Diazomethane

Diazomethane
Diazomethane
Diazomethane
Names
IUPAC name
Diazomethane
Other names
Azimethylene,
Azomethylene,
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.803 Edit this at Wikidata
EC Number
  • 206-382-7
KEGG
UNII
  • InChI=1S/CH2N2/c1-3-2/h1H2 checkY
    Key: YXHKONLOYHBTNS-UHFFFAOYSA-N checkY
  • InChI=1/CH2N2/c1-3-2/h1H2
    Key: YXHKONLOYHBTNS-UHFFFAOYAZ
  • N≡N: N#[N+]-[C-]
  • N=N: [N-]=[N+]=[C]
Properties
CH2N2
Molar mass 42.04 g/mol
Appearance Yellow gas
Odor musty
Density 1.4 (air=1)
Melting point −145 °C (−229 °F; 128 K)
Boiling point −23 °C (−9 °F; 250 K)
hydrolysis[1]
Conjugate acid Methyldiazonium
Structure
linear C=N=N
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic and explosive
GHS labelling:
GHS01: ExplosiveGHS08: Health hazard
Danger
H350
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
4
3
4
Lethal dose or concentration (LD, LC):
175 ppm (cat, 10 min)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.2 ppm (0.4 mg/m3)[2]
REL (Recommended)
 TWA 0.2 ppm (0.4 mg/m3)[2]
IDLH (Immediate danger)
 2 ppm[2]
Related compounds
Related functional groups;
compounds
 R-N=N=N (azide),
R-N=N-R (azo);
R2CN2 R = Ph, tms, CF3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions.[4] Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.[5]

  1. ^ ICSC 1256 – DIAZOMETHANE
  2. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0182". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Diazomethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Proctor, Lee D.; Warr, Antony J. (November 2002). "Development of a Continuous Process for the Industrial Generation of Diazomethane". Organic Process Research & Development. 6 (6): 884–892. doi:10.1021/op020049k.
  5. ^ Shioiri, Takayuki; Aoyama, Toyohiko; Snowden, Timothy (2001). "Trimethylsilyldiazomethane". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt298.pub2. ISBN 0471936235.