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Revision as of 09:36, 25 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 01:19, 1 December 2024 edit undo76.174.0.57 (talk) Distinguish.
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			{{Short description|Organic chemical compound}}
	{{chembox
			{{Distinguish|Methenamine}}
	| verifiedrevid = 398781973
			{{Chembox
	| Name = Methylamine
			| pronounce = {{IPAc-en|ˌ|m|ɛ|θ|ə|l|ə|ˈ|m|iː|n|}}<br/>({{Respell|METH|ə|lə|MEEN}}), {{IPAc-en|ˌ|m|ɛ|θ|ə|ˈ|l|æ|m|ə|n|}}<br/>({{Respell|METH|ə|LA|mən}}), {{IPAc-en|m|ə|ˈ|θ|ɪ|l|ə|ˌ|m|iː|n|}}<br/>({{Respell|mə|THIL|ə|meen}})<ref>{{cite web |url = https://www.dictionary.com/browse/methylamine |title = Methylamine Definition & Meaning |access-date = 22 April 2022 }}</ref>
	| ImageFileL1 = Methylamine-2D.png
			| Verifiedfields = changed
	| ImageSizeL1 = 120px
			| Watchedfields = changed
	| ImageNameL1 = Methylamine
			| verifiedrevid = 415838275
	| ImageFile2 = Methylamine-3D-vdW.png
			| ImageFile = MeNH2.svg
	| ImageSize2 = 120px
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageName2 = Methylamine
			| ImageSize = 200
	| ImageFileR1 = Methylamine-3D-balls.png
			| ImageName = Skeletal formula of methylamine with all explicit hydrogens added
	| ImageSizeR1 = 150px
	| ImageNameR1 = Methylamine		| ImageFileL1 = Methylamine-3D-balls.png
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| IUPACName = aminomethane, methanamine
			| ImageNameL1 = Ball and stick model of methylamine
	| OtherNames = monomethylamine<br />MMA
			| ImageFileR1 = Methylamine-3D-vdW.png
	| Section1 = {{Chembox Identifiers
			| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| SMILES = NC
			| ImageNameR1 = Spacefill model of methylamine
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| PIN = Methanamine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 670 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}}</ref>
	| ChemSpiderID = 6089
			| OtherNames = {{bulletedlist|Aminomethane|Monomethylamine}}
			| Section1 = {{Chembox Identifiers
			| Abbreviations = MMA
			| CASNo = 74-89-5
			| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = BSF23SJ79E
	| PubChem = 6329		| PubChem = 6329
			| ChemSpiderID = 6089
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| EINECS = 200-820-0
			| UNNumber = 1061
			| DrugBank = DB01828
			| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
	| KEGG = C00218		| KEGG = C00218
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/CH5N/c1-2/h2H2,1H3
			| MeSHName = methylamine
	| InChIKey = BAVYZALUXZFZLV-UHFFFAOYAN
			| ChEBI = 16830
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = 43280		| ChEMBL = 43280
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| RTECS = PF6300000
			| Beilstein = 741851
			| Gmelin = 145
			| 3DMet = B00060
			| SMILES = CN
	| StdInChI = 1S/CH5N/c1-2/h2H2,1H3		| StdInChI = 1S/CH5N/c1-2/h2H2,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = BAVYZALUXZFZLV-UHFFFAOYSA-N		| StdInChIKey = BAVYZALUXZFZLV-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| CASNo = 74-89-5
			}}
	| CASNo_Ref = {{cascite|correct|CAS}}
			| Section2 = {{Chembox Properties
	| RTECS = PF6300000
			| Formula = {{chem2|CH3NH2}}
	}}
			| C=1|H=5|N=1
	| Section2 = {{Chembox Properties
			| Appearance = Colorless gas
	| C = 1 | H = 5 | N = 1
			| Odor = Fishy, ammoniacal
	| Appearance = Colorless Gas
	| Density = d<sub>4</sub>0.699 (−10.8 °C) / 0.902 g/cm³, 40w/w% in water		| Density = 0.6562 g/cm<sup>3</sup> (at 25&nbsp;°C)
			| MeltingPtK = 180.05
	| Solubility = 108 g/100 mL (20 °C)
	| MeltingPt = −94 °C (179.15 K)		| BoilingPtK = 266.5 to 267.1
			| Solubility = 1008 g/L (at 20&nbsp;°C)
	| BoilingPt = −6 °C (267.2 K)
			| VaporPressure = 186.10 kPa (at 20&nbsp;°C)
	| pKa = 10.62<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref>
			| LogP = −0.472
	| Viscosity = 0.23 ] at 0 °C
			| HenryConstant = 1.4 mmol/(Pa·kg)
	}}
			| ConjugateAcid = {{chem2|+}} (])
	| Section3 = {{Chembox Structure
			| Viscosity = 230 μPa·s (at 0&nbsp;°C)
	| MolShape = tetrahedral
	| Dipole = 1.31 ] (gas)		| Dipole = 1.31 D
			| pKa = 10.66
	}}
			| MagSus = -27.0·10<sup>−6</sup> cm<sup>3</sup>/mol
	| Section7 = {{Chembox Hazards
			}}
	| ExternalMSDS = From EMD Chemicals
			| Section3 = {{Chembox Thermochemistry
	| MainHazards = Corrosive liquid and gas,<br />inhalation hazard, flammable.
			| DeltaHf = −23.5 kJ/mol
	| NFPA-H = 3
			}}
	| NFPA-F = 4
			| Section4 = {{Chembox Hazards
	| NFPA-R =
			| ExternalSDS =
	| FlashPt = 8 °C
			| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}}
	| RPhrases = 11-36/37 (40% solution in water)
			| GHSSignalWord = '''DANGER'''
	| SPhrases =
			| HPhrases = {{H-phrases|220|315|318|332|335}}
	}}
			| PPhrases = {{P-phrases|210|261|280|305+351+338|410+403}}
	| Section8 = {{Chembox Related
			| NFPA-H = 3
	| Function = ]s
			| NFPA-F = 4
	| OtherFunctn = ]<br /> ]<br /> ]
			| NFPA-R = 0
	}}
			| FlashPtF = 14
			| FlashPt_notes = (liquid, gas is extremely flammable)<ref name=PGCH/>
			| AutoignitionPtC = 430
			| ExploLimits = 4.9–20.7%
			| LD50 = 100 mg/kg (oral, rat)
			| PEL = TWA 10 ppm (12 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0398}}</ref>
			| IDLH = 100 ppm<ref name=PGCH/>
			| LC50 = 1860 ppm (mouse, 2 hr)<ref name=PGCH/>
			| REL = TWA 10 ppm (12 mg/m<sup>3</sup>)<ref name=PGCH/>
			}}
			| Section5 = {{Chembox Related
			| OtherFunction_label = alkanamines
			| OtherFunction = ], ], ]
			| OtherCompounds = ]
			}}
	}}		}}
	'''Methylamine''' is the ] with a ] of CH<sub>3</sub>NH<sub>2</sub>. This colourless gas is a derivative of ], wherein one H atom is replaced by a ] group. It is the simplest primary ]. It is sold as a solution in ], ], ], and ], or as the ] gas in pressurized metal containers. Industrially methylamine is sold in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to fish. Methylamine is used as a building block for the synthesis of many other commercially available compounds. Hundreds of millions of kilograms are produced annually.		'''Methylamine''', also known as '''methanamine''', is an ] with a ] of {{chem2|CH3NH2}}. This colorless gas is a derivative of ], but with one hydrogen atom being replaced by a ]. It is the simplest primary ].
			Methylamine is sold as a solution in ], ], ], or ], or as the ] gas in pressurized metal containers. Industrially, methylamine is transported in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to rotten fish. Methylamine is used as a building block for the synthesis of numerous other commercially available compounds.
	==Production==
	Methylamine is prepared commercially by the reaction of ] with ] in the presence of a silicoaluminate ]. ] and ] are coproduced; the reaction kinetics and reactant ratios determine the ratio of the three products.<ref>{{cite journal
			== Industrial production ==
	| author = Corbin D.R.; Schwarz S.; Sonnichsen G.C.
			Methylamine has been produced industrially since the 1920s (originally by ] for dehairing of animal skins).<ref name=":0" /> This was made possible by {{Interlanguage link|Kazimierz Smoleński|pl}} and his wife Eugenia who discovered amination of alcohols, including methanol, on alumina or kaolin catalyst after WWI, filed two patent applications in 1919<ref>{{Patent|PL|90B1|application}}, {{Patent|PL|91B1|application}}, https://uprp.gov.pl/sites/default/files/2019-12/KWARTALNIK_100_lat_wydanie_specjalne.pdf</ref> and published an article in 1921.<ref name=":0" /><ref>{{Cite book |last=Not Available |url=http://archive.org/details/in.ernet.dli.2015.48294 |title=Chemical Abstracts (1922) Vol.16, No.18 |date=1922}}</ref>
	| title = Methylamines synthesis: A review
			It is now prepared commercially by the reaction of ] with ] in the presence of an ]. ] and ] are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favored by the reaction kinetics is trimethylamine.<ref name=":0">{{cite journal
			|author1=Corbin D.R. |author2=Schwarz S. |author3=Sonnichsen G.C. | title = Methylamines synthesis: A review
	| journal = Catalysis Today		| journal = Catalysis Today
	| year = 1997		| year = 1997
	| volume = 37		| volume = 37
	| issue = 2		| issue = 24
	| pages = 71–102		| pages = 71–102
	| doi = 10.1016/S0920-5861(97)00003-5 }}		| doi = 10.1016/S0920-5861(97)00003-5 }}
	</ref>		</ref>
			:{{chem2|CH3OH + NH3 → CH3NH2 + H2O}}
	:CH<sub>3</sub>OH + NH<sub>3</sub> → CH<sub>3</sub>NH<sub>2</sub> + H<sub>2</sub>O
	In this way, more than 400M kg are produced annually.		In this way, an estimated 115,000 tons were produced in 2005.<ref name=Ullmann/>
			==Laboratory methods==
			Methylamine was first prepared in 1849 by ] via the hydrolysis of ] and related compounds.<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a02_001}}</ref><ref>Charles-Adolphe Wurtz (1849) (On a series of homologous organic alkalis containing ammonia), ''Comptes rendus'' … , '''28''' : 223-226. Note: Wurtz's empirical formula for methylamine is incorrect because chemists in that era used an incorrect atomic mass for carbon (6 instead of 12).</ref> An example of this process includes the use of the ], to yield methylamine from ] and ].<ref>{{cite book|last1= Mann |first1= F. G. |last2= Saunders |first2= B. C.|title=Practical Organic Chemistry|edition=4th|year=1960|publisher=Longman|location=London|isbn=9780582444072|pages=128|url=https://www.scribd.com/doc/46973684/Practical-Organic-Chemistry-Frederick-George-Mann}}</ref><ref>{{cite book|last=Cohen|first=Julius|title=Practical Organic Chemistry|edition=2nd|year=1900|publisher=Macmillan and Co., Limited|location=London|page=|url=https://archive.org/details/practicalorgani00cohegoog}}</ref>
			In the laboratory, methylamine ] is readily prepared by various other methods. One method entails treating ] with ].<ref>{{OrgSynth | author = Marvel, C. S. | author2 = Jenkins, R. L. | title = Methylamine Hydrochloride | collvol = 1 | collvolpages = 347 | year = 1941 | prep = cv1p0347}}</ref>
			:{{chem2|Cl + CH2O → Cl + H2O}}
			:{{chem2|Cl + CH2O + H2O → Cl + ]}}
			The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as ] (NaOH):
			:{{chem2|Cl + NaOH → CH3NH2 + NaCl + H2O}}
			Another method entails reducing ] with ] and hydrochloric acid.<ref>{{cite book|author1=Gatterman, Ludwig |author2=Wieland, Heinrich |name-list-style=amp |title=Laboratory Methods of Organic Chemistry|year=1937|publisher=R & R Clark, Limited|location=Edinburgh, UK|pages=157–158|url=https://books.google.com/books?id=M94cMwEACAAJ&q=Laboratory+Methods+of+Organic+Chemistry+Gattermann+Wieland+Heinrich+1937}}</ref>
			Another method of methylamine production is spontaneous decarboxylation of ] with a strong base in water.<ref>{{Cite journal |last=Callahan |first=Brian P. |last2=Wolfenden |first2=Richard |date=2003-07-31 |title=Migration of Methyl Groups between Aliphatic Amines in Water  . |url=http://dx.doi.org/10.1021/ja033448j |journal=Journal of the American Chemical Society |volume=125 |issue=34 |pages=10481–10481 |doi=10.1021/ja033448j |issn=0002-7863}}</ref>
			== Reactivity and applications ==
			Methylamine is a good ] as it is an unhindered ].<ref>{{cite book | title = Linker Strategies in Solid-Phase Organic Synthesis | date = 13 October 2009 | editor = Peter Scott | url = https://books.google.com/books?id=yZlldxZKBNsC&q=methylamine+unhindered+base&pg=PA80 | page = 80 | publisher = John Wiley & Sons | isbn = 9780470749050 | quote = ...an unhindered amine such as methylamine}}</ref> As an amine it is considered a ]. Its use in ] is pervasive. Some reactions involving simple reagents include: with ] to ], with ] and ] to the sodium methyldithiocarbamate, with ] and base to ] and with ] to ]s. Liquid methylamine has solvent properties analogous to those of ].<ref>{{Cite journal | doi = 10.1021/ja952634p| title = The Lithium−Sodium−Methylamine System: Does a Low-Melting Sodide Become a Liquid Metal?| journal = Journal of the American Chemical Society| volume = 118| issue = 8| pages = 1997| year = 1996| last1 = Debacker| first1 = Marc G.| last2 = Mkadmi| first2 = El Bachir| last3 = Sauvage| first3 = François X.| last4 = Lelieur| first4 = Jean-Pierre| last5 = Wagner| first5 = Michael J.| last6 = Concepcion| first6 = Rosario| last7 = Kim| first7 = Jineun| last8 = McMills| first8 = Lauren E. H.| last9 = Dye| first9 = James L.}}</ref>
			Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ] and ], the pesticides ], ], and ], and the solvents ] and ]. The preparation of some ]s and photographic developers require methylamine as a building block.<ref name=Ullmann/>
	In the laboratory, methylamine ] is readily prepared by the reaction of ] with ] or by treating ] with ].<ref>{{OrgSynth | author = Marvel, C. S.; Jenkins, R. L. | title = Methylamine Hydrochloride | collvol = 1 | collvolpages = 347 | year = 1941 | prep = cv1p0347}}</ref>
	:NH<sub>4</sub>Cl + ] → CH<sub>2</sub>=NH·HCl + H<sub>2</sub>O
	:CH<sub>2</sub>=NH·HCl + H<sub>2</sub>CO + H<sub>2</sub>O → CH<sub>3</sub>NH<sub>2</sub>·HCl + ]
	The colourless hydrochloride salt can be converted to the amine by the addition of strong base, like NaOH:
	:CH<sub>3</sub>NH<sub>2</sub>·HCl + NaOH → CH<sub>3</sub>NH<sub>2</sub> + NaCl + H<sub>2</sub>O
			== Biological chemistry ==
	Methylamine was first prepared by ] by the hydrolysis of ] and related compounds.<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref>
			Methylamine arises as a result of ] and is a substrate for ].<ref>{{Cite journal | doi = 10.1099/00221287-144-9-2377| title = Biochemistry of methanogenesis: A tribute to Marjory Stephenson:1998 Marjory Stephenson Prize Lecture| journal = Microbiology| volume = 144| issue = 9| pages = 2377–406| year = 1998| last1 = Thauer| first1 = R. K.| pmid=9782487| doi-access = free}}</ref>
			Additionally, methylamine is produced during ]-dependent ] ].<ref>{{cite journal|last1=Ng|first1=SS|last2=Yue|first2=WW|last3=Oppermann|first3=U|last4=Klose|first4=RJ|title=Dynamic protein methylation in chromatin biology.|journal=Cellular and Molecular Life Sciences|date=February 2009|volume=66|issue=3|pages=407–22|pmid=18923809|doi=10.1007/s00018-008-8303-z|pmc=2794343}}</ref>
	==Reactivity and applications==
	Methylamine is a good ] as it is highly basic and unhindered, though, as an ] it is considered a ]. Its use in ] is pervasive. Some reactions involving simple reagents include: with phosgene to ], with ] and ] to the sodium methyldithiocarbamate, with chloroform and base to methyl ] and with ] to ]s.
			== Safety ==
	Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ] and ], the pesticides ], ], and ], and the solvents N-methylformamide and N-]. The preparation of some surfactants and photographic developers require methylamine as a building block.<ref name=Ullmann/>
			The ] (mouse, ]) is 2.5 g/kg.<ref>''The Merck Index'', 10th Ed. (1983), p.864, Rahway: Merck & Co.</ref>
			The ] (OSHA) and ] (NIOSH) have set occupational exposure limits at 10 ppm or 12&nbsp;mg/m<sup>3</sup> over an eight-hour time-weighted average.<ref></ref>
	Liquid methylamine can be used as a solvent analogous to ]. It shares some of the properties of liquid ammonia, but is better for dissolving organic substances, in the same way that ] is better than ].<ref>{{cite journal | author = H. D. Gibbs | title = Liquid methylamine as a solvent, and a study of its chemical reactivity | journal = ] | year = 1906 | volume = 28 | pages = 1395–1422 | doi = 10.1021/ja01976a009}}</ref> Methylamine can also be used for scavenging ] from hydrocarbon in refining applications.
			== Regulation ==
	==Biological chemistry==
			In the United States, methylamine is controlled as a ] ] chemical by the ]<ref></ref> due to its use in the illicit production of ].<ref>{{cite journal | doi = 10.1520/JFS12235J| title = The Clandestine Drug Laboratory Situation in the United States| journal = Journal of Forensic Sciences| volume = 28| pages = 18–31| year = 1983| last1 = Frank| first1 = R. S.| issue = 1| pmid = 6680736}}</ref>
	Methylamine arises naturally as the result of ] and is a substrate for ].<ref>Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, 144, 2377-2406.</ref> It serves as a ] in the ] of the ] in plants, effectively siphoning off protons that are heading for ].{{Fact|date=February 2007}}
			== In popular culture ==
	==Safety==
			Fictional characters ] and ] use ] methylamine as part of a process to synthesize ] in the ] series '']''.<ref>{{cite web |website=] |url=https://www.washingtonpost.com/news/wonk/wp/2013/08/15/heres-what-breaking-bad-gets-right-and-wrong-about-the-meth-business/ |title=Here’s what ‘Breaking Bad’ gets right, and wrong, about the meth business |date=15 August 2013 |last=Matthews |first=Dylan |archive-date=3 February 2023 |archive-url=https://web.archive.org/web/20230203140004/https://www.washingtonpost.com/news/wonk/wp/2013/08/15/heres-what-breaking-bad-gets-right-and-wrong-about-the-meth-business/}}</ref><ref>{{cite web |website=Chemistry Views |publisher=] |title=The Chemistry of Breaking Bad |last1=Harnisch |first1=Falk |last2=Salthammer |first2=Tunga |archive-url=https://web.archive.org/web/20240208125657/https://www.chemistryviews.org/details/ezine/5416791/The_Chemistry_of_Breaking_Bad/ |archive-date=8 February 2024 |url=https://www.chemistryviews.org/details/ezine/5416791/The_Chemistry_of_Breaking_Bad/}}</ref>
	The ] (mouse) is 2400 mg/m<sup>3</sup>. Methylamine is also controlled as a List 1 substance by the United States Drug Enforcement Administration (DEA); the ] lists methylamine as a precursor (to ]).
	==References==		==See also==
			*]
	<references/>
			== References ==
	]
			{{Reflist}}
	]
			{{Molecules detected in outer space}}
			{{Authority control}}
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