| Revision as of 12:57, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
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{{distinguish|dimethoxyethane}} |
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{{Redirect-distinguish|Methylal|Methanal|Methylol}} |
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{{Chembox |
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{{Chembox |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 389270413 |
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|verifiedrevid = 414426643 |
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| ImageFile = Dimethoxymethane-2D-skeletal.png |
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|ImageFile = Dimethoxymethane-2D-skeletal.png |
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| ImageName = Structural formula of dimethoxymethane |
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|ImageName = Structural formula of dimethoxymethane |
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| ImageFile1 = Dimethoxymethane-gauche-gauche-conformer-3D-balls.png |
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|ImageFile1 = Dimethoxymethane-gauche-gauche-conformer-3D-balls.png |
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| ImageName1 = Ball and stick model of dimethoxymethane |
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|ImageName1 = Ball and stick model of dimethoxymethane |
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| IUPACName = Dimethoxymethane |
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|PIN = Dimethoxymethane |
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| OtherNames = Formal<br /> |
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|OtherNames = Formal<br /> |
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Formaldehyde dimethyl ether<br /> |
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Formaldehyde dimethyl ether<br /> |
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Methylal |
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Methylal<br /> |
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Dimethylformal (DMFL)<br/> |
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| Section1 = {{Chembox Identifiers |
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Formaldehyde dimethylacetal<br/> |
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| CASNo = 109-87-5 |
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Methoxymethyl methyl ether<br/> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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Methylene dimethyl ether |
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| PubChem = 8020 |
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|Section1={{Chembox Identifiers |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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|CASNo = 109-87-5 |
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| PubChem1 = 10080321 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem1_Comment = (<sup>2</sup>''H''<sub>3</sub>)methoxy |
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| PubChem1_Ref = {{Pubchemcite|correct|PubChem}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 7H1M4G2NUE |
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| PubChem2 = 18424407 |
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|PubChem = 8020 |
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| PubChem2_Comment = sulfane |
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|ChemSpiderID = 13837190 |
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| PubChem2_Ref = {{Pubchemcite|correct|PubChem}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem3 = 21424378 |
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|EINECS = 203-714-2 |
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| PubChem3_Comment = methoxymethane |
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|UNNumber = 1234 |
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| PubChem3_Ref = {{Pubchemcite|correct|PubChem}} |
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|MeSHName = Dimethoxymethane |
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| ChemSpiderID = 13837190 |
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| ChemSpiderID_Ref = {{Chemspidercite|correct|ChemSpider}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 48341 |
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| ChemSpiderID1 = 8255859 |
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|RTECS = PA8750000 |
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| ChemSpiderID1_Comment = (<sup>2</sup>''H''<sub>3</sub>)methoxy |
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|SMILES = COCOC |
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| ChemSpiderID1_Ref = {{Chemspidercite|correct|ChemSpider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| EINECS = 203-714-2 |
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| UNNumber = 1234 |
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|ChEMBL = 15537 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| MeSHName = Dimethoxymethane |
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|StdInChI = 1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
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| ChEBI = 48341 |
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|InChI = 1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
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| RTECS = PA8750000 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = COCOC |
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|StdInChIKey = NKDDWNXOKDWJAK-UHFFFAOYSA-N |
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| ChEMBL = 15537 |
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|InChIKey = NKDDWNXOKDWJAK-UHFFFAOYAE |
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| StdInChI = 1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
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|Beilstein = 1697025 |
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| InChI = 1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
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|Gmelin = 100776}} |
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| StdInChIKey = NKDDWNXOKDWJAK-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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| InChIKey = NKDDWNXOKDWJAK-UHFFFAOYAE |
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|C=3 | H=8 | O=2 |
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| Beilstein = 1697025 |
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|Appearance = Colorless liquid<ref name=Merck>''Merck Index'', 11th Edition, '''5936'''</ref> |
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| Gmelin = 100776}} |
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|Odor = Chloroform-like<ref name=Merck/> |
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| Section2 = {{Chembox Properties |
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|Density = 0.8593 g cm<sup>−3</sup> (at 20 °C)<ref name=Merck/> |
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| C = 3 |
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|MeltingPtC = −105 |
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| H = 8 |
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|MeltingPt_ref = <ref name=Merck/><ref name=inchem>{{ICSC|1152|11}}</ref> |
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| O = 2 |
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|BoilingPtC = 42 |
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| ExactMass = 76.052429500 g mol<sup>-1</sup> |
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|BoilingPt_ref = <ref name=Merck/><ref name=inchem/> |
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| Appearance = Colorless liquid |
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|Solubility = 33% (20 °C)<ref name=PGCH/>{{cln|reason=33% of what? And define "%"! Is it a mass fraction, volume fraction or mole fraction? We cannot read your mind, sorry!|date=May 2023}} |
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| Density = 0.860 g cm<sup>-3</sup> (at 20 °C) |
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|VaporPressure = 330 mmHg (20 °C)<ref name=PGCH/> |
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| MeltingPtC = -32 |
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|MagSus = −47.3·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| BoilingPtC = 42}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = Flammable ('''F''')<br />Irritant ('''Xi''') |
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| RPhrases = {{R11}} {{R36/37/38}} |
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| SPhrases = {{S9}}, {{S16}}, {{S33}} |
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| FlashPt = -18 °C |
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}} |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunctn = ] |
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| OtherCpds = |
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}} |
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}} |
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}} |
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|Section7={{Chembox Hazards |
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'''Dimethoxymethane''', also called methylal, is a clear colorless flammable liquid with a low boiling point, low ] and an excellent dissolving power. It has a ]-like odor and a pungent taste. It is the dimethyl ] of ]. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents. |
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|GHSPictograms = {{GHS02}}{{GHS07}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|225|315|319|335}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|403+235|405|501}} |
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|FlashPtC = −18 |
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|PEL = TWA 1000 ppm (3100 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0396}}</ref> |
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|ExploLimits = 2.2–13.8%<ref name=PGCH/> |
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|IDLH = 2200 ppm<ref name=PGCH/> |
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|LD50 = 5708 mg/kg (rabbit, oral)<ref name=IDLH>{{IDLH|109875|Methylal}}</ref> |
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|LC50 = 18000 ppm (mouse, 7 hr)<br/>15000 ppm (rat)<br/>18354 ppm (mouse, 7 hr)<ref name=IDLH/> |
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|REL = TWA 1000 ppm (3100 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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|Section8={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ] |
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|OtherCompounds = |
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}} |
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}} |
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'''Dimethoxymethane''', also called '''methylal''', is a colorless flammable liquid with a low boiling point, low ] and excellent dissolving power. It has a ]-like odor and a pungent taste. It is the dimethyl ] of ]. Dimethoxymethane is soluble in three parts water{{cln|reason=What on this Earth is "three parts water"? And define "part", because "part" is ambiguous on multiple levels! Is it a mass fraction, volume fraction or mole fraction? We cannot read your mind, sorry!|date=May 2023}} and miscible with most common organic solvents. |
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==Synthesis and structure== |
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It can be manufactured by oxidation of ] or by the reaction of formaldehyde with methanol. In aqueous acid, it is ] back to formaldehyde and methanol. |
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It can be manufactured by oxidation of ] or by the reaction of formaldehyde with methanol. In aqueous acid, it is ] back to formaldehyde and methanol. |
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Due to the ], dimethoxymethane has a preference toward the ''gauche'' ] with respect to each of the C–O bonds, instead of the ''anti'' conformation. Since there are two C–O bonds, the most stable conformation is ''gauche''-''gauche'', which is around 7 kcal/mol more stable than the ''anti''-''anti'' conformation, while the ''gauche''-''anti'' and ''anti-gauche'' are intermediate in energy.<ref>{{Cite book|title=Advanced organic chemistry| last1=Carey|first1=Francis A.| last2=Sundberg|first2=Richard J.| date=2007|publisher=Springer| isbn=9780387448978|edition= 5th|location=New York|oclc=154040953}}</ref> Since it is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, dimethoxymethane is often used for theoretical studies of the anomeric effect. |
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It is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings. |
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==Applications== |
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Another useful application of dimethoxymethane is to protect alcohols with a MOM ether in organic synthesis. This can be done using ] in dry ] or ]. This is a preferred method to using ]. The MOM-ether can be removed using ] and ]. |
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Industrially, it is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings. Another application is as a gasoline-additive for increasing ]. Dimethoxymethane can also be used for blending with diesel. <ref>{{Cite journal|doi = 10.1016/j.combustflame.2020.04.016|title = A comprehensive kinetic model for dimethyl ether and dimethoxymethane oxidation and NO interaction utilizing experimental laminar flame speed measurements at elevated pressure and temperature|year = 2020|last1 = Shrestha|first1 = Krishna P.|last2 = Eckart|first2 = Sven|last3 = Elbaz|first3 = Ayman M.|last4 = Giri|first4 = Binod R.|last5 = Fritsche|first5 = Chris|last6 = Seidel|first6 = Lars|last7 = Roberts|first7 = William L.|last8 = Krause|first8 = Hartmut|last9 = Mauss|first9 = Fabian|journal = Combustion and Flame|volume = 218|pages = 57–74|hdl = 10754/662921|hdl-access = free}}</ref> |
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===Reagent in organic synthesis=== |
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Due to the ], dimethoxymethane has a preference toward the ''gauche'' ] around the C–O bonds, instead of the ''anti'' conformation. Since it is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, dimethoxymethane is often used for theoretical studies of the anomeric effect. |
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Another useful application of dimethoxymethane is to protect alcohols with a methoxymethyl (MOM) ether in organic synthesis. Dimethoxymethane can be activated with ] in ] or ].<ref>{{cite book|last1=Wuts|first1=P. G. M.|last2=Greene, T.W.|year=2006|title=Greene's Protective Groups in Organic Synthesis|doi=10.1002/0470053488|isbn= 9780470053485|publisher=J. Wiley|location=NY}}</ref> This method is preferred to the use of ] (MOMCl). Phenols can also be MOM-protected using dimethoxymethane, ].<ref>{{cite journal |last1=Yardley |first1=John P. |last2=Fletcher |first2=Horace |title=Introduction of the Methoxymethyl Ether Protecting Group |journal=Synthesis |date=1976 |volume=1976 |issue=04 |pages=244–244 |doi=10.1055/s-1976-24000}}</ref> Alternatively, MOMCl can be generated as a solution by treating dimethoxymethane with an acyl chloride in the presence of a Lewis acid catalyst like ]: |
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:MeOCH<sub>2</sub>OMe + RC(=O)Cl → MeOCH<sub>2</sub>Cl + RC(=O)(OMe)). |
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Unlike the classical procedure, which uses formaldehyde and hydrogen chloride as starting materials, the highly carcinogenic side product ] is not generated.<ref>{{cite journal |title=Synthesis of alpha-Halo Ethers from Symmetric Acetals and ''in situ'' Methoxymethylation of an Alcohol |journal=Organic Syntheses |date=2007 |volume=84 |pages=102 |doi=10.15227/orgsyn.084.0102|first1=Martin|last1= Berliner|first2=Katherine|last2=Belecki.|doi-access=free}}</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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*''Merck Index'', 11th Edition, '''5936''' |
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==External links== |
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==External links== |
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* {{ICSC|1152|11}} |
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* {{PGCH|0396}} |
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* {{PGCH|0396}} |
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{{Authority control}} |
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