Ethenone

Ethenone
Structural formula
Space-filling model
Names
Preferred IUPAC name
Ethenone[1]
Other names
Ketene
Carbomethene
Keto-ethylene
Identifiers
3D model (JSmol)
1098282
ChEBI
ChemSpider
ECHA InfoCard 100.006.671 Edit this at Wikidata
EC Number
  • 207-336-9
RTECS number
  • OA7700000
UNII
  • InChI=1S/C2H2O/c1-2-3/h1H2 checkY
    Key: CCGKOQOJPYTBIH-UHFFFAOYSA-N checkY
  • InChI=1/C2H2O/c1-2-3/h1H2
    Key: CCGKOQOJPYTBIH-UHFFFAOYSA-N
  • InChI=1/C2H2O/c1-2-3/h1H2
    Key: CCGKOQOJPYTBIH-UHFFFAOYAO
  • O=C=C
Properties
C2H2O
Molar mass 42.037 g/mol
Appearance Colourless gas
Odor penetrating
Density 1.93 g/cm3
Melting point −150.5 °C (−238.9 °F; 122.6 K)
Boiling point −56.1 °C (−69.0 °F; 217.1 K)
decomposes
Solubility soluble in acetone
ethanol
ethyl ether
aromatic solvents
halocarbons
Vapor pressure >1 atm (20°C)[2]
1.4355
Thermochemistry
51.75 J/K mol
-87.24 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
4
1
Flash point −107 °C (−161 °F; 166 K)
Explosive limits 5.5-18%
Lethal dose or concentration (LD, LC):
1300 mg/kg (oral, rat)
17 ppm (mouse, 10 min)[3]
23 ppm (mouse, 30 min)
53 ppm (rabbit, 2 hr)
53 ppm (guinea pig, 2 hr)
750 ppm (cat, 10 min)
200 ppm (monkey, 10 min)
50 ppm (mouse, 10 min)
1000 ppm (rabbit, 10 min)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.5 ppm (0.9 mg/m3)[2]
REL (Recommended)
 TWA 0.5 ppm (0.9 mg/m3) ST 1.5 ppm (3 mg/m3)[2]
IDLH (Immediate danger)
 5 ppm[2]
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).
☒N verify (what is checkY☒N ?)

Ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.[4][5]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0367". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Ketene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_063. ISBN 3527306730.
  5. ^ Mitzel, Thomas M.; Pigza, Julie A. (2009). "Ketene". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rk000.pub2. ISBN 978-0-471-93623-7.