Dimethylacetamide

Dimethylacetamide
Names
IUPAC name
N,N-Dimethylacetamide[1]
Identifiers
3D model (JSmol)
Abbreviations DMA, DMAC, DMAc[2]
1737614
ChEBI
ChemSpider
ECHA InfoCard 100.004.389
EC Number 204-826-4
MeSH dimethylacetamide
RTECS number AB7700000
UNII
Properties
C4H9NO
Molar mass 87.12 g·mol−1
Appearance Colorless liquid
Odor Ammoniacal
Density 0.937 g mL−1
Melting point −20 °C (−4 °F; 253 K)
Boiling point 165.1 °C; 329.1 °F; 438.2 K
Miscible
log P −0.253
Vapor pressure 300 Pa
UV-vis (λmax) 270 nm
Absorbance 1.00
1.4375
Viscosity 0.945 mPa s [3]
Thermochemistry
178.2 J K−1 mol−1
−300.1 kJ mol−1
−2.5835–−2.5805 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H312, H319, H332, H360
P280, P308+313
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
2
2
0
Flash point 63 °C (145 °F; 336 K)
490 °C (914 °F; 763 K)
Explosive limits 1.8–11.5%
Lethal dose or concentration (LD, LC):
2.24 g kg−1 (dermal, rabbit)
4.3 g kg−1 (oral, rat)
4.8 g/kg (oral, rat)
4.62 g/kg (oral, mouse)[4]
2475 ppm (rat, 1 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 10 ppm (35 mg/m3) [skin][5]
REL (Recommended)
 TWA 10 ppm (35 mg/m3) [skin][5]
IDLH (Immediate danger)
 300 ppm[5]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

Synthesis, reactions, applications

DMA is prepared by the reaction of dimethylamine with acetic anhydride and esters of acetic acid. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound:[6]

CH3CO2H·HN(CH3)2 → H2O + CH3CON(CH3)2

The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. It will hydrolyze in the presence of acids:

CH3CON(CH3)2 + H2O + HCl → CH3COOH + (CH3)2NH2+Cl−

It is however resistant to bases. For this reason DMA is useful solvent for reactions involving strong bases such as sodium hydroxide.[7]

Dimethylacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the adhesive industry.[6] It is also employed in the production of pharmaceuticals and plasticizers as a reaction medium. It is an important Lewis base used to establish the ECW Model.

Dimethylacetamide is also used as an excipient in drugs, e.g. in Vumon (teniposide), Busulfex (busulfan) or Amsidine (amsacrine).

Toxicity

Dimethylacetamide is a medium potency reproductive toxicant (toxic for reproduction, category 1B)[8] and may damage fertility or the unborn child. It is harmful in contact with skin or if inhaled, and causes serious eye irritation.

Dimethylacetamide can cause hepatotoxicity, including occupational dimethylacetamide exposure-induced hepatotoxicity.[9][10][11][12] At high doses (400 mg/kg bodyweight daily), dimethylacetamide causes effects on the central nervous system (e.g. depression, hallucinations and delusion).[9][13][14]

Dimethylacetamide may be incompatible with polycarbonate or ABS. Devices (e.g. syringes) that contain polycarbonate or ABS can dissolve when coming into contact with dimethylacetamide.[15]

Regulation

In 2011, dimethylacetamide was identified in the EU as a Substance of very high concern (SVHC) because of its reproductive toxicity.[16] In 2014, the European Commission has started an investigation to restrict the use of dimethylacetamide in the EU according to REACH.[17]

In 2015, the CNESST (Committee on Standards, Equity, Health and Safety at Work in Quebec) has adopted a tightened classification of dimethylacetamide:[18]

Description Category GHS hazard statement
Reproductive toxicity 2 Suspected of damaging fertility or the unborn child (H361)
Specific target organ toxicity - repeated exposure 2 May cause damage to organs through prolonged or repeated exposure (H373)
Serious eye damage/eye irritation 2 Causes serious eye irritation (H319)
Acute toxicity - inhalation 3 Toxic if inhaled (H331)
Specific target organ toxicity - single exposure - narcotic effects 3 May cause drowsiness or dizziness (H336)
Flammable liquid 4 Combustible liquid (H227)

References

  1. ↑ "dimethylacetamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 2005-03-26. Identification. Retrieved 2012-04-19.
  2. ↑ Munro, D. D.; Stoughton, R. B. (1965). "Dimethylacetamide (DMAC) and Dimethylformamide (DMFA). Effect on Percutaneous Absorption". Archives of Dermatology. 92 (5): 585–586. PMID 5844405. doi:10.1001/archderm.1965.01600170101020.
  3. ↑ Iloukhani, H., and 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 the liquid region and at ambient pressure." Journal of Chemical & Engineering Data 51.4 (2006): 1226-1231. doi:10.1021/je050538q
  4. 1 2 "Dimethyl acetamide". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 3 "NIOSH Pocket Guide to Chemical Hazards #0218". National Institute for Occupational Safety and Health (NIOSH).
  6. 1 2 Cheung, H.; Tanke, R. S.; Torrence, G. P. (2005), "Acetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_045.pub2
  7. ↑ Zen, S.; Kaji, E. (1977). "Dimethyl nitrosuccinate". Org. Synth. 57: 60.; Coll. Vol., 6, p. 503
  8. ↑ European Chemicals Agency, Opinion on N,N-Dimethylacetamide (DMAC), 12 September 2014
  9. 1 2 U.S. Department of Health and Human Services & U.S. Department of Labor (1978) Occupational Health Guideline for Dimethyl Acetamide. Now: Occupational Health Guideline for Chemical Hazards. DHHS (NIOSH) Publication Number 81-123. January 1981. The National Institute for Occupational Safety and Health (NIOSH).
  10. ↑ Baum, S. L.; Suruda, A. J. (1997). "Toxic Hepatitis from Dimethylacetamide". International Journal of Occupational and Environmental Health. 3 (1): 1–4. PMID 9891094. doi:10.1179/oeh.1997.3.1.1.
  11. ↑ Lee, C.-Y.; Jung, S.-J.; Kim, S.-A.; Park, K.-S.; Ha, B.-G. (2006). "Incidence of dimethylacetamide induced hepatic injury among new employees in a cohort of elastane fibre workers". Occupational and Environmental Medicine. 63 (10): 688–693. PMC 2078052 Freely accessible. PMID 16728503. doi:10.1136/oem.2005.023580.
  12. ↑ Gong, W.; Liu, X.; Zhu, B. (2016). "Dimethylacetamide-induced occupational toxic hepatitis with a short term recurrence: a rare case report". Journal of Thoracic Disease. 8 (6): E408–E411. PMC 4885965 Freely accessible. PMID 27293868. doi:10.21037/jtd.2016.04.44.
  13. ↑ Weiss, A. J.; Jackson, L. G.; Carabasi, R. A.; Mancall, E. L.; White, J. C. (1962). "A Phase I Study of Dimethylacetamide". Cancer Chemotherapy Reports. 16 (February 1962): 477–485. PMID 14005853.
  14. ↑ Weiss, A. J.; Mancall, E. L.; Koltes, J. A.; White, J. C.; Jackson, L. G. (1962). "Dimethylacetamide: A Hitherto Unrecognized Hallucinogenic Agent". Science. 136 (3511): 151–152. PMID 14005854. doi:10.1126/science.136.3511.151.
  15. ↑ FDA warns health care professionals not to use Treanda Injection (solution) with closed system transfer devices, adapters, and syringes containing polycarbonate or acrylonitrile-butadiene-styrene – 10 March 2015
  16. ↑ Agreement of the Member State Committee on the Identification of N,N-Dimethylacetamide (DMAC) as a Substance of Very High Concern – Adopted on 24 November 2011
  17. ↑ Official Journal of the European Union, 19.8.2014, Commission Regulation (EU) No 895/2014
  18. ↑ Commission des normes, de l'équité, de la santé et de la sécurité du travail (CNESST), Quebec, Canada: WHMIS 2015 classification of N,N-Dimethylacetamide
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