Diazomethane

Diazomethane
Names
	IUPAC name Diazomethane
	Other names Azimethylene,; Azomethylene,;
Identifiers
CAS Number	334-88-3 ;
3D model (JSmol)	N≡N: Interactive image; N=N: Interactive image;
ChEBI	CHEBI:73716 ;
ChemSpider	9176 ;
ECHA InfoCard	100.005.803
EC Number	206-382-7;
KEGG	C19387 ;
PubChem CID	9550;
UNII	60A625P70P ;
CompTox Dashboard (EPA)	DTXSID0024008 ;
	InChI InChI=1S/CH2N2/c1-3-2/h1H2 Key: YXHKONLOYHBTNS-UHFFFAOYSA-N ; InChI=1/CH2N2/c1-3-2/h1H2 Key: YXHKONLOYHBTNS-UHFFFAOYAZ;
	SMILES N≡N: N#[N+]-[C-]; N=N: [N-]=[N+]=[C];
Properties
Chemical formula	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)
Solubility in water	hydrolysis
Conjugate acid	Methyldiazonium
Structure
Molecular shape	linear C=N=N
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	toxic and explosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H350
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)	4 3 4
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	175 ppm (cat, 10 min)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.2 ppm (0.4 mg/m3)
REL (Recommended)	TWA 0.2 ppm (0.4 mg/m3)
IDLH (Immediate danger)	2 ppm
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). verify (what is ?) Infobox references

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]

^ ICSC 1256 – DIAZOMETHANE
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0182". National Institute for Occupational Safety and Health (NIOSH).
^ "Diazomethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ 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.

[1] ICSC 1256 – DIAZOMETHANE

[PGCH-2] 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).

[proctor-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.

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[3]

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[4]

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Names


IUPAC name Diazomethane
Other names Azimethylene, Azomethylene,
Identifiers
CAS Number	334-88-3^Y
3D model (JSmol)	N≡N: Interactive image N=N: Interactive image
ChEBI	CHEBI:73716^N
ChemSpider	9176^Y
ECHA InfoCard	100.005.803
EC Number	206-382-7
KEGG	C19387^Y
PubChem CID	9550
UNII	60A625P70P^Y
CompTox Dashboard (EPA)	DTXSID0024008
InChI InChI=1S/CH2N2/c1-3-2/h1H2^Y Key: YXHKONLOYHBTNS-UHFFFAOYSA-N^Y InChI=1/CH2N2/c1-3-2/h1H2 Key: YXHKONLOYHBTNS-UHFFFAOYAZ
SMILES N≡N: N#[N+]-[C-] N=N: [N-]=[N+]=[C]
Properties
Chemical formula	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)
Solubility in water	hydrolysis^[1]
Conjugate acid	Methyldiazonium
Structure
Molecular shape	linear C=N=N
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	toxic and explosive
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H350
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)	4 3 4
Lethal dose or concentration (LD, LC):
LC₅₀ (median concentration)	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). N verify (what is ^YN ?) Infobox references