Ethyl carbamate

Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks.

Ethyl carbamate
Names
Preferred IUPAC name
Ethyl carbamate
Other names
Carbamic acid ethyl ester, Urethane, Ethylurethane
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.113
EC Number
  • 200-123-1
KEGG
MeSH Urethane
PubChem CID
RTECS number
  • FA8400000
UNII
UN number 2811
  • InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5) Y
    Key: JOYRKODLDBILNP-UHFFFAOYSA-N Y
  • InChI=1/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
    Key: JOYRKODLDBILNP-UHFFFAOYAY
SMILES
  • CCOC(N)=O
  • O=C(OCC)N
Properties
C3H7NO2
Molar mass 89.094 g·mol−1
Appearance White crystals
Density 1.056 g cm−3
Melting point 46 to 50 °C (115 to 122 °F; 319 to 323 K)
Boiling point 182 to 185 °C (360 to 365 °F; 455 to 458 K)
0.480 g cm−3 at 15 °C
log P -0.190(4)
Vapor pressure 1.3 kPa at 78 °C
Acidity (pKa) 13.58
2.59 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful if swallowed
May cause cancer
GHS labelling:
Danger
H302, H350
P201, P301+P312+P330, P308+P313
NFPA 704 (fire diamond)
1
2
0
Flash point 92 °C (198 °F; 365 K)
Related compounds
Related compounds
Methyl carbamate
Propyl carbamate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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