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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 399907716 |
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|Watchedfields = changed |
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| Name = Dimethylacetamide |
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|verifiedrevid = 414427167 |
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| ImageFileL1 = Dimethylacetamide.svg |
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|ImageFile = Dimethylacetamide.svg |
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| ImageSizeL1 = 110px |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1 = Dimethylacetamide-3D-balls-B.png |
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|ImageSize = 100 |
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| ImageSizeR1 = 130px |
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| ImageName = Chemical structure of dimethyalcetamide |
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|ImageName = Skeletal formula of dimethylacetamide |
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| IUPACName = Dimethylacetamide |
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|ImageFile1 = Dimethylacetamide-3D-balls-B.png |
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|ImageFile1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = DMAc, DMA, acetic acid-dimethylamide, N,N-dimethylacetamide, acetyldimethylamine |
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|ImageSize1 = 160 |
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| Section1 = {{Chembox Identifiers |
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|ImageName1 = Ball and stick model of dimethylacetamide |
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| SMILES = O=C(N(C)C)C |
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|PIN = ''N'',''N''-Dimethylacetamide |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 29107 |
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|Abbreviations = DMA, DMAC, DMAc<ref>{{ cite journal |author1=Munro, D. D. |author2=Stoughton, R. B. | title = Dimethylacetamide (DMAC) and Dimethylformamide (DMFA). Effect on Percutaneous Absorption | journal = Archives of Dermatology | year = 1965 | volume = 92 | issue = 5 | pages = 585–586 | doi = 10.1001/archderm.1965.01600170101020 | pmid = 5844405}}</ref> |
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| PubChem = 31374 |
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|CASNo = 127-19-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII = JCV5VDB3HY |
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|PubChem = 31374 |
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| InChI = 1/C4H9NO/c1-4(6)5(2)3/h1-3H3 |
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|ChemSpiderID = 29107 |
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| InChIKey = FXHOOIRPVKKKFG-UHFFFAOYAE |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL = 11873 |
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|UNII = JCV5VDB3HY |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChI = 1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 |
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|EINECS = 204-826-4 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|MeSHName = dimethylacetamide |
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| StdInChIKey = FXHOOIRPVKKKFG-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEBI = 84254 |
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| CASNo = 127-19-5 |
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|ChEMBL = 11873 |
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| RTECS = AB7700000 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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}} |
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|RTECS = AB7700000 |
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| Section2 = {{Chembox Properties |
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|Beilstein = 1737614 |
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| C=4|H=9|N=1|O=1 |
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|SMILES = CN(C)C(C)=O |
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| Appearance = Colorless liquid with<br />faint ammonia odor |
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|StdInChI = 1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 |
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| Density = 0.94 g/cm<sup>3</sup> |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| MeltingPtC = -20 |
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|StdInChIKey = FXHOOIRPVKKKFG-UHFFFAOYSA-N |
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| BoilingPt = 164-166 °C |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Refractive index = 1.4375 |
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}} |
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| Viscosity = 1.956 cP @ 25 °C<br/> |
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|Section2={{Chembox Properties |
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1.279 cP @ 50 °C<br/> |
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|C=4 | H=9 | N=1 | O=1 |
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0.896 cP @ 75 °C<br/> |
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|Appearance = Colorless liquid |
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0.661 cP @ 100 °C}} |
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|Odor = Ammoniacal |
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| Section7 = {{Chembox Hazards |
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|Density = 0.937 g/mL |
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| MainHazards = Toxic ('''T''') |
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|MeltingPtC = −20 |
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| RPhrases = {{R61}} {{R20/21}} |
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|BoilingPtK = 438.2 |
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| SPhrases = {{S53}} {{S45}} |
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|Solubility = Miscible |
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| NFPA-H = 2 |
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|LogP = −0.253 |
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| NFPA-F = |
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|VaporPressure = 300 Pa |
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| NFPA-R = |
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| FlashPt = 70 °C |
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|LambdaMax = 270 nm |
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|RefractIndex = 1.4375 |
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| Autoignition = 490 °C |
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|Viscosity = 0.945 mPa·s <ref>Iloukhani, H., K. Khanlarzadeh. "Densities, viscosities, and refractive indices for binary and ternary mixtures of N, N-dimethylacetamide (1)+ 2-methylbutan-2-ol (2)+ ethyl acetate (3) at 298.15 K for m liquid region and at ambient pressure". Journal of Chemical & Engineering Data, 51.4 (2006): 1226–1231. {{doi|10.1021/je050538q}}.</ref> |
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}} |
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| Section8 = {{Chembox Related |
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|Section3={{Chembox Thermochemistry |
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| Function = ]s |
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|DeltaHf = −300.1 kJ/mol |
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| OtherFunctn = ''N'',''N''-] |
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|DeltaHc = −2.5835–−2.5805 MJ/mol |
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| Function = Compounds |
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|HeatCapacity = 178.2 J/(K·mol) |
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| OtherFunctn = ]<br />]<br />] |
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|Section4={{Chembox Hazards |
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|GHSPictograms = {{gHS exclamation mark}} {{gHS health hazard}} |
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|GHSSignalWord = '''DANGER''' |
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|HPhrases = {{h-phrases|312|319|332|360}} |
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|PPhrases = {{p-phrases|280|308+313}} |
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|NFPA-H = 2 |
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|NFPA-F = 2 |
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|NFPA-R = 0 |
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|FlashPtC = 63 |
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|AutoignitionPtC = 490 |
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|ExploLimits = 1.8–11.5% |
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|LD50 = 2.24 g/kg <small>(dermal, rabbit)</small><br />4.3 g/kg <small>(oral, rat)</small><br />4.8 g/kg (oral, rat)<br />4.62 g/kg (oral, mouse)<ref name=IDLH/> |
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|PEL = TWA 10 ppm (35 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0218}}</ref> |
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|IDLH = 300 ppm<ref name=PGCH/> |
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|REL = TWA 10 ppm (35 mg/m<sup>3</sup>) <ref name=PGCH/> |
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|LC50 = 2475 ppm (rat, 1 ])<ref name=IDLH>{{IDLH|127195|Dimethyl acetamide}}</ref> |
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|Section5={{Chembox Related |
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|OtherCompounds = {{Unbulleted list|]|]|]}} |
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'''Dimethylacetamide''' is the ] with the ] CH<sub>3</sub>C(O)N(CH<sub>3</sub>)<sub>2</sub>. This colorless, water miscible, high boiling liquid is commonly used as a polar ] in organic chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in ] ]s. |
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'''Dimethylacetamide''' ('''DMAc''' or '''DMA''') is the ] with the ] CH<sub>3</sub>C(O)N(CH<sub>3</sub>)<sub>2</sub>. This colorless, water-miscible, high-boiling liquid is commonly used as a polar ] in ]. DMA is miscible with most other solvents, although it is poorly soluble in ] ]s. |
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==Synthesis and production== |
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The chemical reactions of dimethylacetamide are typical of ''N'',''N''-disubstituted ]s. It will ] in the presence of ]s: |
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DMA is prepared commercially by the reaction of ] with ] or ]. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound:<ref name=Ullmann>{{ Ullmann | author = Cheung, H. | author2 = Tanke, R. S. | author3 = Torrence, G. P. | title = Acetic Acid | doi = 10.1002/14356007.a01_045.pub2}}</ref> |
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: CH<sub>3</sub>CO<sub>2</sub>H·HN(CH<sub>3</sub>)<sub>2</sub> → H<sub>2</sub>O + CH<sub>3</sub>CON(CH<sub>3</sub>)<sub>2</sub> |
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Dimethylacetamide can also be produced by the reaction of ] with ].<ref name="production">{{cite web |last1=Grafmans |first1=Horst |last2=Maas |first2=Steffen |last3=Weck |first3=Alexander |last4=Rütter |first4=Heinz |last5=Schulz |first5=Michael |last6=Ross |first6=Karl-Heinz |title=Method for the production of n,n-dimethylacetamide (DMAC) |url=https://patents.google.com/patent/EP1828102B1/en |website=Google Patents |publisher=BASF SE |accessdate=18 July 2019}}</ref> |
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: CH<sub>3</sub>CON(CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>O + HCl → CH<sub>3</sub>COOH + (CH<sub>3</sub>)<sub>2</sub>NH<sub>2</sub><sup>+</sup>Cl<sup>-</sup> |
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: ] |
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Dimethylacetamide is useful as a medium for strong bases such as ].<ref>{{OrgSynth | author = S. Zen and E. Kaji | title = Dimethyl nitrosuccinate | collvol = 6 | collvolpages = 503 | year = 1988 | prep = CV6P0503}}</ref> Dimethylacetamide is commonly used as a solvent for fibers or in the ] industry. It is also employed in the production of ] and ]s as a reaction medium. |
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The separation and purification of the product is carried out by multistage ] in rectification columns. DMA is obtained with essentially quantitive (99%) ] referred to methyl acetate.<ref name=production/> |
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==Reactions and applications== |
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The chemical reactions of dimethylacetamide are typical of ''N'',''N''-disubstituted ]s. ] of the acyl-N bond occurs in the presence of ]s: |
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: CH<sub>3</sub>CON(CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>O + HCl → CH<sub>3</sub>COOH + (CH<sub>3</sub>)<sub>2</sub>NH<sub>2</sub><sup>+</sup>Cl<sup>−</sup> |
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However, it is resistant to bases. For this reason DMA is a useful solvent for reactions involving strong bases such as ].<ref>{{OrgSynth | author = Zen, S. | author2 = Kaji, E. | title = Dimethyl nitrosuccinate | volume = 57 | pages = 60 | collvol = 6 | collvolpages = 503 | year = 1977 | prep = CV6P0503}}</ref> |
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Dimethylacetamide is commonly used as a solvent for fibers (e.g., ], ]) or in the ] industry.<ref name=Ullmann/> It is also employed in the production of ] and ]s as a reaction medium. |
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A solution of ] in DMAc (LiCl/DMAc) can dissolve ]. Unlike many other cellulose solvents, LiCl/DMAc gives a molecular dispersion, i.e. a "true solution". For this reason, it is used in ] to determine the ] of cellulose samples. |
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Dimethylacetamide is also used as an ] in drugs, e.g. in Vumon (]), Busulfex (]) or Amsidine (]). |
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==Toxicity== |
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Dimethylacetamide, like most simple alkyl amides, is of low acute toxicity. Chronic exposure can cause ].<ref name="cdc.gov">U.S. Department of Health and Human Services & U.S. Department of Labor (1978) . Now: Occupational Health Guideline for Chemical Hazards. . January 1981. The National Institute for Occupational Safety and Health (NIOSH).</ref><ref>{{ cite journal |author1=Baum, S. L. |author2=Suruda, A. J. | title = Toxic Hepatitis from Dimethylacetamide | journal = International Journal of Occupational and Environmental Health | year = 1997 | volume = 3 | issue = 1 | pages = 1–4 | doi = 10.1179/oeh.1997.3.1.1 | pmid = 9891094 }}</ref><ref>{{ cite journal |author1=Lee, C.-Y. |author2=Jung, S.-J. |author3=Kim, S.-A. | author4=Park, K.-S. | author5=Ha, B.-G. | title = Incidence of dimethylacetamide induced hepatic injury among new employees in a cohort of elastane fibre workers | journal = Occupational and Environmental Medicine | year = 2006 | volume = 63 | issue = 10 | pages = 688–693 | doi = 10.1136/oem.2005.023580 | pmid = 16728503 | pmc = 2078052 }}</ref><ref>{{ cite journal |author1=Gong, W. |author2=Liu, X. |author3=Zhu, B. | title = Dimethylacetamide-induced occupational toxic hepatitis with a short term recurrence: a rare case report | journal = Journal of Thoracic Disease | year = 2016 | volume = 8 | issue = 6 | pages = E408–E411 | doi = 10.21037/jtd.2016.04.44 | pmid = 27293868 | pmc = 4885965 |doi-access=free }}</ref> At high doses (400 mg/kg body mass daily), dimethylacetamide causes effects on the ] (e.g. ], ]s and ]).<ref name="cdc.gov"/><ref>{{ cite journal |author1= Weiss, A. J. |author2= Jackson, L. G. |author3= Carabasi, R. A. | author4= Mancall, E. L. | author5= White, J. C. | title = A Phase I Study of Dimethylacetamide | journal = Cancer Chemotherapy Reports | year = 1962 | volume = 16 | issue = February 1962 | pages = 477–485 | pmid = 14005853}}</ref><ref>{{ cite journal |author1= Weiss, A. J. |author2= Mancall, E. L. |author3= Koltes, J. A. | author4= White, J. C. | author5= Jackson, L. G. | title = Dimethylacetamide: A Hitherto Unrecognized Hallucinogenic Agent | journal = Science | year = 1962 | volume = 136 | issue = 3511 | pages = 151–152| doi = 10.1126/science.136.3511.151| pmid = 14005854|bibcode= 1962Sci...136..151W |s2cid= 20098340 }}</ref> |
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Dimethylacetamide may be incompatible with ] or ]. Devices (e.g. syringes) that contain polycarbonate or ABS can dissolve when coming into contact with dimethylacetamide.<ref>. 10 March 2015.</ref> |
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==Regulation== |
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In 2011, dimethylacetamide was identified in the EU as a ] (SVHC) because of its ].<ref>.</ref> In 2014, the European Commission has started an investigation to restrict the use of dimethylacetamide in the EU according to ].<ref>, Official Journal of the European Union, 19.08.2014.</ref> |
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In 2015, the CNESST (Committee on Standards, Equity, Health and Safety at Work in ]) has adopted a tightened classification of dimethylacetamide:<ref>Commission des normes, de l'équité, de la santé et de la sécurité du travail (CNESST), Quebec, Canada: .</ref> |
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{| class="wikitable" |
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! Description !! Category !! ] |
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| Reproductive toxicity || 2|| Suspected of damaging fertility or the unborn child (H361) |
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| Specific target organ toxicity – repeated exposure || 2|| May cause damage to organs through prolonged or repeated exposure (H373) |
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| Serious eye damage/eye irritation || 2|| Causes serious eye irritation (H319) |
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| Acute toxicity – inhalation || 3|| Toxic if inhaled (H331) |
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| Specific target organ toxicity – single exposure – narcotic effects || 3|| May cause drowsiness or dizziness (H336) |
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| Flammable liquid || 4|| Combustible liquid (H227) |
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==See Also== |
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* ] |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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==External links== |
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