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Revision as of 11:48, 1 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI', 'StdInChI', 'StdInChIKey').← Previous edit		Latest revision as of 06:55, 7 January 2025 edit undo103.49.48.125 (talk) →Structure and properties
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 458288128
			| verifiedrevid = 458446617
	| Name = ''N'',''N''-Dimethylformamide
	| ImageFileL1 = Dimethylformamide-2D-skeletal.svg		| ImageFile = Dimethylformamide-2D-skeletal.svg
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageNameL1 = Chemical structure of dimethylformamide
			| ImageSize = 100
	| ImageFileR1 = DMF-3D-balls.png
			| ImageName = Skeletal formula of dimethylformamide with one explicit hydrogen added
	| ImageNameR1 = Dimethylformamide
			| ImageFileL1 = DMF-3D-balls.png
	| IUPACName = ''N'',''N''-Dimethylmethanamide
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| OtherNames = DMF; Dimethylformamide; ''N'',''N''-Dimethylformamide; DMFA
			| ImageNameL1 = Ball and stick model of dimethylformamide
	| Section1 = {{Chembox Identifiers
			| ImageFileR1 = Dimethylformamide-3D-vdW.png
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| ImageNameR1 = Spacefill model of dimethylformamide
	| DrugBank = DB01844
			| PIN = ''N'',''N''-Dimethylformamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 841, 844 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The traditional name ‘formamide’ is retained for HCO-NH<sub>2</sub> and is the preferred IUPAC name. Substitution is permitted on the –NH<sub>2</sub> group.}}</ref>
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| SystematicName = ''N'',''N''-Dimethylmethanamide<ref>, NIST web thermo tables</ref>
	| StdInChI = 1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
			| OtherNames = Dimethylformamide<br />DMF
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| IUPACName =
	| StdInChIKey = ZMXDDKWLCZADIW-UHFFFAOYSA-N
			| Section1 = {{Chembox Identifiers
	| SMILES = O=CN(C)C
			|CASNo = 68-12-2
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			|CASNo_Ref = {{cascite|correct|CAS}}
	| ChEMBL = 268291
			|PubChem = 6228
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 5993		|ChemSpiderID = 5993
	| UNII_Ref = {{fdacite|correct|FDA}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| UNII = 8696NH0Y2X		|UNII = 8696NH0Y2X
			|UNII_Ref = {{fdacite|correct|FDA}}
	| InChI = 1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
			|EINECS = 200-679-5
	| InChIKey = ZMXDDKWLCZADIW-UHFFFAOYSA-N
	| CASNo = 68-12-2		|UNNumber = 2265
			|DrugBank = DB01844
	| CASNo_Ref = {{cascite|correct|CAS}}
			|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| RTECS = LQ2100000
	| ChEBI = 17741		|KEGG = C03134
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| PubChem = 6228
			|MeSHName = Dimethylformamide
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C03134		|ChEBI = 17741
			|ChEBI_Ref = {{ebicite|correct|EBI}}
			|ChEMBL = 268291
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
			|RTECS = LQ2100000
			|Beilstein = 605365
			|3DMet = B00545
			|SMILES = CN(C)C=O
			|StdInChI = 1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey = ZMXDDKWLCZADIW-UHFFFAOYSA-N
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			}}
			| Section2 = {{Chembox Properties
			|C=3|H=7|N=1|O=1
			|Appearance = Colourless liquid
			|Odor = Odorless, fishy if impure
			|Density = 0.948 g/mL
			|MeltingPtC = -61
			|BoilingPtC = 153
			|pKa = −0.3 (for the conjugate acid) (H<sub>2</sub>O)<ref>{{cite web | title = Hazardous Substances Data Bank (HSDB) - N,N-DIMETHYLFORMAMIDE | url = https://pubchem.ncbi.nlm.nih.gov/source/hsdb/78}}</ref>
			|Solubility = Miscible
			|LogP = −0.829
			|VaporPressure = 516 Pa
			|LambdaMax = 270 nm
			|Absorbance = 1.00
			|RefractIndex = 1.4305 (at 20&nbsp;°C)
			|Viscosity = 0.92 mPa·s (at 20&nbsp;°C)
			}}
			| Section3 = {{Chembox Structure
			|Dipole = 3.86 D
			}}
			| Section4 = {{Chembox Thermochemistry
			|DeltaHf = −239.4 ± 1.2 kJ/mol
			|DeltaHc = −1.9416 ± 0.0012 MJ/mol
			|HeatCapacity = 146.05 J/(K·mol)
			}}
			| Section5 = {{Chembox Hazards
			|GHSPictograms = {{gHS flame}} {{gHS exclamation mark}} {{gHS health hazard}}
			|GHSSignalWord = '''DANGER'''
			|HPhrases = {{h-phrases|226|312|319|332|360}}
			|PPhrases = {{p-phrases|280|305+351+338|308+313}}
			|NFPA-H = 2
			|NFPA-F = 2
			|NFPA-R = 0
			|FlashPtC = 58
			|AutoignitionPtC = 445
			|ExploLimits = 2.2–15.2%
			|TLV-TWA = 30 mg/m<sup>3</sup>
			|LD50 = {{unbulleted list|1.5 g/kg <small>(rabbit, dermal)</small>|2.8 g/kg <small>(rat, oral)</small>|3.7 g/kg <small>(mouse, oral)</small>|3.5 g/kg <small>(rat, oral)</small>}}
			|PEL = TWA 10 ppm (30 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0226}}</ref>
			|IDLH = 500 ppm<ref name=PGCH/>
			|REL = TWA 10 ppm (30 mg/m<sup>3</sup>) <ref name=PGCH/>
			|LC50 = 3092 ppm (mouse, 2 ])<ref name=IDLH>{{IDLH|68122|Dimethylformamide}}</ref>
			|LCLo = 5000 ppm (rat, 6 h)<ref name=IDLH/>
			}}
			| Section6 = {{Chembox Related
			|OtherFunction_label = alkanamides
			|OtherFunction = {{unbulleted list|]|]|]}}
			|OtherCompounds = {{unbulleted list|]|]}}
	}}		}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>3</sub>H<sub>7</sub>NO
	| MolarMass = 73.09 g/mol
	| Appearance = Clear liquid
	| Density = 0.944 g/cm<sup>3</sup>, liquid
	| Solubility = Miscible
	| MeltingPtC = -61
	| BoilingPtC = 153
	| VaporPressure = 0.3 kPa (@ 20°C)
	| pKa =
	| pKb =
	| Viscosity = 0.92 ] at 20 °C
	| RefractIndex = 1.4305 (20 °C), ] = 36.71 (25°C)
	}}
	| Section3 = {{Chembox Structure
	| Dipole = 3.86 ] (25 °C)
	}}
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| MainHazards = flammable
	| NFPA-H = 1
	| NFPA-F = 2
	| NFPA-R = 0
	| FlashPt = 58 °C
	| RPhrases = {{R61}} {{R20/21}} {{R36}}
	| SPhrases = {{S53}} {{S45}}
	| TLV-TWA = 10 ppm<ref></ref>
	}}
	| Section8 = {{Chembox Related
	| Function = ]s
	| OtherFunctn = ],<br />],<br />]
	| OtherCpds = ],<br />],<br />]
	}}
	}}		}}
	'''Dimethylformamide''' is an ] with the ] (])<sub>2</sub>NC(O)H. Commonly abbreviated DMF (though this acronym is sometimes used for ]), this colourless liquid is miscible with ] and the majority of organic liquids. DMF is a common ] for ]. Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of ]. Its name is derived from the fact that it is a derivative of ], the ] of ].		'''Dimethylformamide''', '''DMF''' is an ] with the ] {{chem2|HCON(CH3)2|auto=1}}. Its structure is {{chem2|HC(\dO)\sN(])2}}. Commonly abbreviated as DMF (although this initialism is sometimes used for ], or ]), this colourless liquid is ] with ] and the majority of organic liquids. DMF is a common ] for ]. Dimethylformamide is odorless, but ] or degraded samples often have a fishy smell due to impurity of ]. Dimethylamine degradation impurities can be removed by ] samples with an inert gas such as ] or by ] the samples under reduced pressure. As its name indicates, it is structurally related to ], having two ]s in the place of the two hydrogens. DMF is a ] (]) ] with a high ]. It facilitates reactions that follow polar mechanisms, such as ] reactions.
	Dimethylformamide is a ] (]) ] with a high ]. It facilitates reactions that follow polar mechanisms, such as ] reactions. Dimethylformamide can be synthesized from ] and ] or by reaction of dimethylamine with ].<ref name="indchem">{{cite book
	| author = Klaus Weissermel, Hans-Jürgen Arpe
	| title = Industrial Organic Chemistry: Important Raw Materials and Intermediates
	| publisher = Wiley-VCH
	| isbn = 3527305785
	| pages = 45–46
	}}</ref> Dimethylformamide is not stable in the presence of strong bases like ] or strong acids such as ] or ] and is ] back into formic acid and dimethylamine, especially at elevated temperatures.
	==Structure and properties==		==Structure and properties==
	Due to the contribution of the two possible resonance structures of an amide, the bond order of the ] C=O bond is reduced, while that of the ] is increased. Thus the ] of DMF shows a lower C=O stretching frequency at 1675&nbsp;cm<sup>−1</sup><ref name=SDBS>Spectral Database for Organic Compounds, , accessed 27 Jan 2007.</ref> than an unsubstituted C=O bond. Also, because of the partial double bond character, the rotation about the C-N axis is slow at room temperature, making the two methyl groups inequivalent on the ] time scale, giving rise to two singlets of 3 protons each at δ 2.97 and 2.88,<ref name=SDBS/> instead of one singlet of 6 protons in the ] spectrum.		As for most ]s, the spectroscopic evidence indicates partial double bond character for the C−N and C−O bonds.Thus, the ] shows a C=O stretching frequency at only 1675&nbsp;cm<sup>−1</sup>, whereas a ketone would absorb near 1700&nbsp;cm<sup>−1</sup>.<ref name=SDBS>{{cite web | publisher = AIST | location = Japan | work = Spectral Database for Organic Compounds | url = http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_frame_disp.cgi?sdbsno=324 | title = Dimethylformamide | access-date = 2012-06-28}}{{Dead link|date=July 2019 |bot=InternetArchiveBot |fix-attempted=yes}}</ref>
			DMF is a classic example of a ].<ref>{{cite journal | author1 = H. S. Gutowsky | author2 = C. H. Holm | title = Rate Processes and Nuclear Magnetic Resonance Spectra. II. Hindered Internal Rotation of Amides | journal = J. Chem. Phys. | year = 1956 | volume = 25 | pages = 1228–1234 | doi=10.1063/1.1743184 | issue = 6|bibcode = 1956JChPh..25.1228G}}</ref>
	N,N-Dimethylformamide (DMF) is miscible with water in all proportions.<ref name=bipp>{{cite book|author=Bipp, H. and Kieczka, H. |year=1989|title=Ullmann’s Encyclopedia of Industrial Chemistry|edition=5|volume= A12|pages=1–12|publisher= VCH Verlagsgesellschaft|place=Weinheim}}</ref> The vapour pressure at 20°C is 3.5hPa.<ref>IPCS (International Programme on Chemical Safety) (1991). Environmental Health Criteria 114 “Dimethylformamide” United Nations Environment Programme, International Labour Organisation, World Health Organization; 1-124.</ref> A ] constant of 7.47×10<sup>−5</sup> hPa·m<sup>3</sup>/mol can be deduced from an experimentally determined equilibrium constant at 25 °C.<ref>{{cite journal|author=Taft, R.W. ''et al.''|title=The molecular properties governing solubilities of organic nonelectrolytes in water|journal=Nature |volume=313|pages=384–386|year=1985|doi=10.1038/313384a0|issue=6001}}</ref> The ] logPOW is measured to –0.85.<ref>(BASF AG, department of analytical, unpublished data, J-No. 124659/08, 27.11.1987)</ref> Since the density of DMF (0.95 g/cm<sup>3</sup> at 20 °C<ref name=bipp/>) is very similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.
			]
			The ambient temperature ] shows two methyl signals, indicative of hindered rotation about the (O)C−N bond.<ref name=SDBS/> At temperatures near 100&nbsp;°C, the 500&nbsp;MHz NMR spectrum of this compound shows only one signal for the methyl groups.
			DMF is miscible with water.<ref name=bipp>{{Ullmann | author = Bipp, H. | author2 = Kieczka, H. | title = Formamides | doi = 10.1002/14356007.a12_001.pub2}}</ref> The vapour pressure at 20&nbsp;°C is 3.5&nbsp;hPa.<ref>IPCS (International Programme on Chemical Safety) (1991). Environmental Health Criteria 114 "Dimethylformamide" United Nations Environment Programme, International Labour Organisation, World Health Organization; 1–124.</ref> A ] constant of 7.47 × 10<sup>−5</sup> hPa·m<sup>3</sup>/mol can be deduced from an experimentally determined equilibrium constant at 25&nbsp;°C.<ref>{{cite journal |author1=Taft, R. W. |author2=Abraham, M. H. |author3=Doherty, R. M. |author4=Kamlet, M. J. | title = The molecular properties governing solubilities of organic nonelectrolytes in water | journal = ] | year = 1985 | volume = 313 | issue = 6001 | pages = 384–386 | doi = 10.1038/313384a0 |bibcode=1985Natur.313..384T |s2cid=36740734}}</ref> The ] log&nbsp;''P''<sub>OW</sub> is measured to −0.85.<ref>(BASF AG, department of analytical, unpublished data, J-No. 124659/08, 27.11.1987)</ref> Since the density of DMF (0.95&nbsp;g·cm<sup>&minus;3</sup> at 20&nbsp;°C<ref name=bipp/>) is similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.
	]{{Clearleft}}
			]{{Clear left}}
			==Reactions==
			DMF is hydrolyzed by strong acids and bases, especially at elevated temperatures. With ], DMF converts to formate and dimethylamine. DMF undergoes ] near its boiling point to give dimethylamine. Distillation is therefore conducted under reduced pressure at lower temperatures.<ref>{{Cite encyclopedia|title = ''N'',''N''-Dimethylformamide|encyclopedia = Encyclopedia of Reagents for Organic Synthesis|last1 = Comins|first1 = Daniel L.|last2 = Joseph|first2 = Sajan P.|year = 2001|publisher = ]|isbn = 9780470842898|doi = 10.1002/047084289x.rd335|chapter = N,N-Dimethylformamide}}</ref>
			In one of its main uses in ], DMF is a reagent in the ], which is used to formylate aromatic compounds.<ref name = VH1>{{cite journal|author-link1 = Anton Vilsmeier|last1 = Vilsmeier|first1 = Anton|last2 = Haack|first2 = Albrecht|title = Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer ''p''-Alkylamino-benzaldehyde|language = de|trans-title=On the reaction of phosphorus halides with alkyl formanilides. A new method for the preparation of secondary and tertiary ''p''-alkylamino-benzaldehyde|year = 1927|journal = ]|volume = 60|issue = 1|pages = 119–122|doi = 10.1002/cber.19270600118}}</ref><ref name = VH2>{{cite book|last1 = Meth-Cohn|first1 = Otto|last2 = Stanforth|first2 = Stephen P.|chapter = The Vilsmeier-Haack Reaction|title = Additions to CX π-Bonds, Part 2|series = Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry|year = 1993|volume = 2|editor1-first = Barry M.|editor1-last = Trost|editor1-link = Barry M. Trost|editor2-first = Clayton H.|editor2-last = Heathcock|editor2-link = Clayton H. Heathcock|pages = 777–794|doi = 10.1016/B978-0-08-052349-1.00049-4|publisher = ]|isbn = 9780080405933}}</ref> The process involves initial conversion of DMF to a chloroiminium ion, <sup>+</sup>, known as a ],<ref>{{cite journal|title = The Vilsmeier Reaction of Non-Aromatic Compounds|first1 = Gurnos|last1 = Jones|first2 = Stephen P.|last2 = Stanforth|journal = ]|year = 2000|volume = 56|issue = 2|pages = 355–686|doi = 10.1002/0471264180.or056.02}}</ref> which attacks arenes.
			]s and ]s react with DMF to give ]s after hydrolysis in a reaction called ].<ref name="Wang-2009">{{cite book |last1=Wang |first1=Zerong |title=Comprehensive organic name reactions and reagents |date=2009 |publisher=John Wiley |location=Hoboken, N.J. |isbn=9780471704508 |pages=490–492}}</ref>
			Dimethylformamide forms 1:1 ] with a variety of Lewis acids such as the soft acid ], and the hard acid ]. It is classified as a ] and its ] base parameters are E<sub>B</sub> = 2.19 and C<sub>B</sub> = 1.31.<ref>{{cite journal|author1=Vogel G. C. |author2=Drago, R. S. |year=1996|journal=Journal of Chemical Education|volume=73|pages=701–707|title=The ECW Model|issue=8 |bibcode=1996JChEd..73..701V|doi=10.1021/ed073p701}}</ref> Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by ].<ref>Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9</ref><ref>{{cite journal|author1=Cramer, R. E. |author2=Bopp, T. T. |year=1977|title= Graphical display of the enthalpies of adduct formation for Lewis acids and bases |journal= Journal of Chemical Education |volume=54|pages=612–613|doi= 10.1021/ed054p612}} The plots shown in this paper used older parameters. Improved E&C parameters are listed in ]. </ref>
	==Production==		==Production==
			DMF was first prepared in 1893 by the French chemist Albert Verley (8 January 1867 – 27 November 1959), by distilling a mixture of dimethylamine hydrochloride and ].<ref>{{cite journal|last1=Verley|first1=A.|title=Sur la préparation des amides en général|journal=Bulletin de la Société Chimique de Paris|date=1893|volume=9|pages=690–692|url=https://babel.hathitrust.org/cgi/pt?id=uc1.a0008581456;view=1up;seq=700|series=3rd series|trans-title=On the preparation of amides in general|language=fr}} On p. 692, Verley states that DMF is prepared by a procedure analogous to that for the preparation of dimethylacetamide (see p. 691), which would be by distilling dimethylamine hydrochloride and ].</ref>
	Dimethyl formamide is produced either via catalyzed reaction of ] and ] in methanol <!--at low pressure and temperature (contadicts the reference)--> or via the reaction of ] with dimethylamine.<ref name="indchem" /> It may also be prepared on a laboratory scale by reacting dimethylamine with ].{{Citation needed|date=February 2010}}
			DMF is prepared by combining ] and ] or by reaction of dimethylamine with ].<ref name="indchem">{{cite book |author1=Weissermel, K. |author2=Arpe, H.-J. | title = Industrial Organic Chemistry: Important Raw Materials and Intermediates | publisher = Wiley-VCH | isbn = 3-527-30578-5 | pages = 45–46 |year=2003}}</ref>
			Although currently impractical, DMF can be prepared from ] using ]-based catalysts.<ref>{{cite book|author1=Walter Leitner|author2=Philip G. Jessop|title=Chemical synthesis using supercritical fluids|url=https://books.google.com/books?id=-9yqpBozUuYC&pg=PA408|access-date=27 June 2011|year=1999|publisher=Wiley-VCH|isbn=978-3-527-29605-7|pages=408–}}</ref>
	==Applications==		==Applications==
	The primary use of dimethylformamide is as a solvent with low evaporation rate. DMF is used in the production of ] and ]. It is also used as a solvent in ] for pharmaceuticals, in the development and production of ], and in the manufacture of ], synthetic ], fibers, films, and surface coatings.<ref name=dmf-uses>{{cite journal | last1 = Redlich | first1 = C | last2 = Beckett | first2 = W. S. | last3 = Sparer | first3 = J. | last4 = Barwick | first4 = K. W. | last5 = Riely | first5 = C. A. | last6 = Miller | first6 = H. | last7 = Sigal | first7 = S. L. | last8 = Shalat | first8 = S. L. | last9 = Cullen | first9 = M. R. ''et al.'' | year = 1988 | title = Liver disease associated with occupational exposure to the solvent dimethylformamide | url = | journal = Ann. Intern. Med. | volume = 108 | issue = 5| pages = 680–686 | pmid = 3358569 }}</ref>		The primary use of DMF is as a solvent with low evaporation rate. DMF is used in the production of ] and ]. It is also used as a solvent in ] for pharmaceuticals, in the development and production of ], and in the manufacture of ], synthetic ]s, fibers, films, and surface coatings.<ref name=bipp/>
			*It is used as a reagent in the ]<ref>{{cite journal|last = Bouveault|first = Louis|author-link = Louis Bouveault|journal = Bulletin de la Société Chimique de Paris|year = 1904|series=3rd series|volume = 31|pages = 1306–1322|title = Modes de formation et de préparation des aldéhydes saturées de la série grasse|language = fr|trans-title = Methods of preparation of saturated aldehydes of the aliphatic series|url=https://babel.hathitrust.org/cgi/pt?id=uc1.a0004784781;view=1up;seq=1410}}</ref><ref>{{cite journal|last = Bouveault|first = Louis|author-link = Louis Bouveault|journal = Bulletin de la Société Chimique de Paris|year = 1904|series=3rd series|volume = 31|pages = 1322–1327|title = Nouvelle méthode générale synthétique de préparation des aldéhydes|trans-title = Novel general synthetic method for preparing aldehydes|language = fr|url=https://babel.hathitrust.org/cgi/pt?id=uc1.a0004784781;view=1up;seq=1426}}</ref><ref>{{cite book|last = Li|first = Jie Jack|title = Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications|edition = 5th|chapter = Bouveault aldehyde synthesis|pages = 72–73|chapter-url = https://books.google.com/books?id=HoXBBAAAQBAJ&pg=PA72|year = 2014|publisher = ]|isbn = 978-3-319-03979-4}}</ref> and in the ],<ref name = VH1 /><ref name = VH2 /> another useful method of forming ].
	*It is used as a reagent in the ] and in the ], another useful method of forming ].
			*It is a common solvent in the ].<ref>{{cite book|title = The Mizoroki&ndash;Heck Reaction|editor-first = Martin|editor-last = Oestreich|publisher = ]|year = 2009|isbn = 9780470716069}}</ref>
	*It is also a common catalyst used in the synthesis of ], in particular the synthesis of ] from ] using ] or ].<ref name = clayden>{{cite book |author=Clayden, Jonathan |title=Organic chemistry |publisher=Oxford University Press |location=Oxford |year=2001 |pages=276–296 |isbn=0-19-850346-6 |oclc= |doi= |accessdate=}}</ref>
			*It is a common catalyst used in the synthesis of ], in particular the synthesis of ] from ] using ] or ]. The catalytic mechanism entails reversible formation of an ] (also known as the 'Vilsmeier reagent'):<ref name = clayden>{{cite book | author = Clayden, J. | title = Organic Chemistry | publisher = Oxford University Press | location = Oxford | year = 2001 | pages = | isbn = 0-19-850346-6 | url-access = registration | url = https://archive.org/details/organicchemistry00clay_0/page/276}}</ref><ref>Ansell, M. F. in "The Chemistry of Acyl Halides"; S. Patai, Ed.; John Wiley and Sons: London, 1972; pp 35–68.</ref>
	*DMF penetrates most ] and makes them ]. This property makes it very suitable for ]. It also frequently occurs as a component of ] for this purpose.
	*DMF is very effective at separating and suspending ], and is recommended by the ] for use in ] of such.<ref name=miiswcn>{{cite journal
			]
	| author = Haddon, Robert
	| coauthors = Itkis, Mikhail
			*DMF penetrates most ] and makes them swell. Because of this property DMF is suitable for ] and as a component of ].
	| title = Measurement Issues in Single Wall Carbon Nanotubes
	| publisher = NIST
	| date = March, 2008
	| url = http://www.nist.gov/public_affairs/practiceguides/NIST%20SP960-19.pdf
	| format = ]
	| pages = 20
	| accessdate = 2008-08-15
	}}</ref>
	*DMF can be utilized as a standard in proton NMR allowing for a quantitative determination of an unknown chemical.
	*DMF is used as a solvent to recover ] such as ] via ].		*DMF is used as a solvent to recover ] such as ] via ].
	*It is also used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.		*It is used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.
	*Pure ] gas cannot be compressed and stored without the danger of explosion. Industrial acetylene gas is, therefore, dissolved in dimethylformamide and stored in metal cylinders or bottles. The casing is also filled with ], which renders it safe to transport and use.		*Pure ] gas cannot be compressed and stored without the danger of explosion. Industrial acetylene is safely compressed in the presence of dimethylformamide, which forms a safe, concentrated solution. The casing is also filled with ], which renders it safe to transport and use.
			As a cheap and common reagent, DMF has many uses in a research laboratory.
			*DMF is effective at separating and suspending ], and is recommended by the ] for use in ] of such.<ref name=miiswcn>{{cite book |author1=Haddon, R. |author2=Itkis, M. |editor1=Freiman, S. |editor2=Hooker, S. |editor3=Migler |editor4=K. |editor5=Arepalli, S. | title = Publication 960-19 Measurement Issues in Single Wall Carbon Nanotubes | chapter = 3. Near-Infrared (NIR) Spectroscopy | publisher = NIST |date=March 2008 | chapter-url = https://www.nist.gov/customcf/get_pdf.cfm?pub_id=852726 | chapter-format = pdf | page = 20 | access-date = 2012-06-28}}</ref>
			*DMF can be utilized as a standard in proton NMR spectroscopy allowing for a quantitative determination of an unknown compound.
			*In the synthesis of organometallic compounds, it is used as a source of ] ligands.
			*DMF is a common solvent used in ].
			*DMF is commonly used in the solvothermal synthesis of ].
			*DMF-''d''<sub>7</sub> in the presence of a catalytic amount of ] under microwave heating is a reagent for deuteration of polyaromatic hydrocarbons.
	==Safety==		==Safety==
			Dimethylformamide vapor exposure has shown reduced alcohol tolerance and skin irritation in some cases.<ref>{{cite journal | pmc=1008494 | year=1979 | last1=Lyle | first1=W. H. | last2=Spence | first2=T. W. | last3=McKinneley | first3=W. M. | last4=Duckers | first4=K. | title=Dimethylformamide and alcohol intolerance | journal=British Journal of Industrial Medicine | volume=36 | issue=1 | pages=63–66 | doi=10.1136/oem.36.1.63 | pmid=444443}}</ref>
	Reactions including the use of ] in DMF as a solvent are somewhat hazardous; exothermic decompositions have been reported at temperatures as low as 26 °C. On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents. On a ] scale, on the other hand, several accidents have been reported.<ref> and references cited therein</ref>
			On 20 June 2018, the ] published an article about DMF's use in ]. The density of the compound in the toy resulted in all squishies being removed from the Danish market. All squishies were recommended to be thrown out as household waste.
			<ref>{{cite web | title = Skumlegetøj afgiver farlige kemikalier (in English- Squishies giving dangerous chemicals) | url = https://mst.dk/service/nyheder/nyhedsarkiv/2018/jun/skumlegetoej-afgiver-farlige-kemikalier/ | author1 = Magnus Løfstedt | access-date = 2019-06-13 | archive-date = 2021-09-03 | archive-url = https://web.archive.org/web/20210903082250/https://mst.dk/service/nyheder/nyhedsarkiv/2018/jun/skumlegetoej-afgiver-farlige-kemikalier/ | url-status = dead}}</ref>
	==Toxicity==		==Toxicity==
			The acute ] (oral, rats and mice) is 2.2–7.55 g/kg.<ref name=bipp/> Hazards of DMF have been examined.<ref name=dmf-uses>{{cite journal |author1=Redlich, C. |author2=Beckett, W. S. |author3=Sparer, J. |author4=Barwick, K. W. |author5=Riely, C. A. |author6=Miller, H. |author7=Sigal, S. L. |author8=Shalat, S. L. |author9=Cullen, M. R. | title = Liver disease associated with occupational exposure to the solvent dimethylformamide | journal = Annals of Internal Medicine | year = 1988 | volume = 108 | issue = 5 | pages = 680–686 | pmid = 3358569 | doi=10.7326/0003-4819-108-5-680}}</ref>
	DMF has been linked to ] in humans, and it is thought to cause ] <ref> for Dimethylformamide</ref>. In some sectors of industry women are banned from working with DMF. For many reactions, it can be replaced with ]. Most manufacturers of DMF list (Life) or (Chronic) as a health hazard in their MSDS since DMF is not readily disposed of by the body. According to ], DMF is a possible ], although ] does not consider it a cancer risk.
	==References==		==References==
	{{reflist|2}}		{{Reflist|35em}}
	==External links==		==External links==
	*{{ICSC|0457|04}}		*{{ICSC|0457|04}}
	*{{PGCH|0226}}		*{{PGCH|0226}}
	*Dimethylformamide usage on
	*		*
	* for DMF
	* (])
	*(])
	* (])
			{{Authority control}}
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