Acetamide

Acetamide
Names
Preferred IUPAC name
Acetamide[1]
Systematic IUPAC name
Ethanamide
Other names
Acetic acid amide
Acetylamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430 Edit this at Wikidata
EC Number
  • 200-473-5
KEGG
RTECS number
  • AB4025000
UNII
  • InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) checkY
    Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N checkY
  • InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
    Key: DLFVBJFMPXGRIB-UHFFFAOYAC
  • O=C(N)C
Properties
C2H5NO
Molar mass 59.068 g·mol−1
Appearance colorless, hygroscopic solid
Odor odorless
mouse-like with impurities
Density 1.159 g cm−3
Melting point 79 to 81 °C (174 to 178 °F; 352 to 354 K)
Boiling point 221.2 °C (430.2 °F; 494.3 K) (decomposes)
2000 g L−1[2]
Solubility ethanol 500 g L−1[2]
pyridine 166.67 g L−1[2]
soluble in chloroform, glycerol, benzene[2]
log P −1.26
Vapor pressure 1.3 Pa
Acidity (pKa) 15.1 (25 °C, H2O)[3]
−0.577 × 10−6 cm3 g−1
1.4274
Viscosity 2.052 cP (91 °C)
Structure
trigonal
Thermochemistry[4]
91.3 J·mol−1·K−1
115.0 J·mol−1·K−1
−317.0 kJ·mol−1
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H351
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
7000 mg kg−1 (rat, oral)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is an amide derived from ammonia and acetic acid. It finds some use as a plasticizer and as an industrial solvent.[5] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral[6] with the IMA symbol: Ace.[7]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d The Merck Index, 14th Edition, 36
  3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
  4. ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
  5. ^ Cite error: The named reference ullmann was invoked but never defined (see the help page).
  6. ^ Mindat: Naturally occurring acetamide
  7. ^ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols". Mineralogical Magazine. 85 (3): 291–320. Bibcode:2021MinM...85..291W. doi:10.1180/mgm.2021.43. S2CID 235729616.