Phosgene

Phosgene^[1]
	; A sample case of toxic gases used in chemical warfare; the leftmost contains phosgene in a sealed capillary
Names
	Preferred IUPAC name Carbonyl dichloride
	Other names Carbon dichloride oxide; Carbon oxychloride; Carbonyl chloride; CG; Chloroformyl chloride; Collongite; Dichloroformaldehyde; Dichloromethanal; Dichloromethanone;
Identifiers
CAS Number	75-44-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29365 ;
ChemSpider	6131 ;
ECHA InfoCard	100.000.792
EC Number	200-870-3;
PubChem CID	6371;
RTECS number	SY5600000;
UNII	117K140075 ;
UN number	1076
CompTox Dashboard (EPA)	DTXSID0024260 ;
	InChI InChI=1S/CCl2O/c2-1(3)4 Key: YGYAWVDWMABLBF-UHFFFAOYSA-N ; InChI=1/CCl2O/c2-1(3)4 Key: YGYAWVDWMABLBF-UHFFFAOYAH;
	SMILES ClC(Cl)=O;
Properties
Chemical formula	COCl2
Molar mass	98.91 g·mol−1
Appearance	Colorless gas
Odor	Suffocating, like musty hay or grass
Density	4.248 g/L (15 °C, gas); 1.432 g/cm3 (0 °C, liquid)
Melting point	−118 °C (−180 °F; 155 K)
Boiling point	8.3 °C (46.9 °F; 281.4 K)
Solubility in water	Insoluble, reacts
Solubility	Soluble in benzene, toluene, acetic acid; Decomposes in alcohol and acid
Vapor pressure	1.6 atm (20°C)
Magnetic susceptibility (χ)	−48·10−6 cm3/mol
Structure
Molecular shape	Trigonal planar
Dipole moment	1.17 D
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H280, H314, H330
Precautionary statements	P260, P280, P303+P361+P353+P315, P304+P340+P315, P305+P351+P338+P315, P403, P405
NFPA 704 (fire diamond)	4 0 1
Flash point	Non-flammable
Threshold limit value (TLV)	0.1 ppm (1 ppm = 4 mg/m3)
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	500 ppm (human, 1 min); 340 ppm (rat, 30 min); 438 ppm (mouse, 30 min); 243 ppm (rabbit, 30 min); 316 ppm (guinea pig, 30 min); 1022 ppm (dog, 20 min); 145 ppm (monkey, 1 min); 1 ppm is 4 mg/m3;
LCLo (lowest published)	3 ppm (human, 2.83 h); 30 ppm (human, 17 min); 50 ppm (mammal, 5 min); 88 ppm (human, 30 min); 46 ppm (cat, 15 min); 50 ppm (human, 5 min); 2.7 ppm (mammal, 30 min); 1 ppm is 4 mg/m3;
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.1 ppm (0.4 mg/m3)
REL (Recommended)	TWA 0.1 ppm (0.4 mg/m3) C 0.2 ppm (0.8 mg/m3) [15-minute]
IDLH (Immediate danger)	2 ppm; 1 ppm = 4 mg/m3
Safety data sheet (SDS)	[1]
Related compounds
Related compounds	Thiophosgene; Formaldehyde; Carbonic acid; Urea; Carbon monoxide; Chloroformic acid; Phosgene oxime;
	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

Phosgene is an organic chemical compound with the formula COCl₂. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass.^[7] It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

Phosgene is extremely poisonous and was used as a chemical weapon during World War I, where it was responsible for 85,000 deaths. It is a highly potent pulmonary irritant and quickly filled enemy trenches due to it being a heavy gas.

It is classified as a Schedule 3 substance under the Chemical Weapons Convention. In addition to its industrial production, small amounts occur from the breakdown and the combustion of organochlorine compounds, such as chloroform.^[8]

^ Merck Index, 11th Edition, 7310.
^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 798. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0504". National Institute for Occupational Safety and Health (NIOSH).
^ "PHOSGENE (cylinder)". Inchem (Chemical Safety Information from Intergovernmental Organizations). International Programme on Chemical Safety and the European Commission.
^ ^a ^b ^c Record of Phosgene in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 16 March 2021.
^ ^a ^b "Phosgene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ CBRNE - Lung-Damaging Agents, Phosgene May 27, 2009
^ Wolfgang Schneider; Werner Diller. "Phosgene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_411. ISBN 978-3527306732.

[1] Merck Index, 11th Edition, 7310.

[iupac2013-2] Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 798. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0504". National Institute for Occupational Safety and Health (NIOSH).

[4] "PHOSGENE (cylinder)". Inchem (Chemical Safety Information from Intergovernmental Organizations). International Programme on Chemical Safety and the European Commission.

[GESTIS-5] Record of Phosgene in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 16 March 2021.

[IDLH-6] "Phosgene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[7] CBRNE - Lung-Damaging Agents, Phosgene May 27, 2009

[Ullmann-8] Wolfgang Schneider; Werner Diller. "Phosgene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_411. ISBN 978-3527306732.

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Names


A sample case of toxic gases used in chemical warfare; the leftmost contains phosgene in a sealed capillary
Preferred IUPAC name Carbonyl dichloride^[2]
Other names Carbon dichloride oxide Carbon oxychloride Carbonyl chloride CG Chloroformyl chloride Collongite Dichloroformaldehyde Dichloromethanal Dichloromethanone
Identifiers
CAS Number	75-44-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29365^Y
ChemSpider	6131^Y
ECHA InfoCard	100.000.792
EC Number	200-870-3
PubChem CID	6371
RTECS number	SY5600000
UNII	117K140075^Y
UN number	1076
CompTox Dashboard (EPA)	DTXSID0024260
InChI InChI=1S/CCl2O/c2-1(3)4^Y Key: YGYAWVDWMABLBF-UHFFFAOYSA-N^Y InChI=1/CCl2O/c2-1(3)4 Key: YGYAWVDWMABLBF-UHFFFAOYAH
SMILES ClC(Cl)=O
Properties
Chemical formula	COCl₂
Molar mass	98.91 g·mol⁻¹
Appearance	Colorless gas
Odor	Suffocating, like musty hay or grass^[3]
Density	4.248 g/L (15 °C, gas) 1.432 g/cm³ (0 °C, liquid)
Melting point	−118 °C (−180 °F; 155 K)
Boiling point	8.3 °C (46.9 °F; 281.4 K)
Solubility in water	Insoluble, reacts^[4]
Solubility	Soluble in benzene, toluene, acetic acid Decomposes in alcohol and acid
Vapor pressure	1.6 atm (20°C)^[3]
Magnetic susceptibility (χ)	−48·10⁻⁶ cm³/mol
Structure
Molecular shape	Trigonal planar
Dipole moment	1.17 D
Hazards
GHS labelling:
Pictograms	^[5]
Signal word	Danger
Hazard statements	H280, H314, H330^[5]
Precautionary statements	P260, P280, P303+P361+P353+P315, P304+P340+P315, P305+P351+P338+P315, P403, P405^[5]
NFPA 704 (fire diamond)	4 0 1
Flash point	Non-flammable
Threshold limit value (TLV)	0.1 ppm (1 ppm = 4 mg/m³)
Lethal dose or concentration (LD, LC):
LC₅₀ (median concentration)	500 ppm (human, 1 min) 340 ppm (rat, 30 min) 438 ppm (mouse, 30 min) 243 ppm (rabbit, 30 min) 316 ppm (guinea pig, 30 min) 1022 ppm (dog, 20 min) 145 ppm (monkey, 1 min) 1 ppm is 4 mg/m³ ^[6]
LC_Lo (lowest published)	3 ppm (human, 2.83 h) 30 ppm (human, 17 min) 50 ppm (mammal, 5 min) 88 ppm (human, 30 min) 46 ppm (cat, 15 min) 50 ppm (human, 5 min) 2.7 ppm (mammal, 30 min) 1 ppm is 4 mg/m³ ^[6]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.1 ppm (0.4 mg/m³)^[3]
REL (Recommended)	TWA 0.1 ppm (0.4 mg/m³) C 0.2 ppm (0.8 mg/m³) [15-minute]^[3]
IDLH (Immediate danger)	2 ppm^[3] 1 ppm = 4 mg/m³
Safety data sheet (SDS)	[1]
Related compounds
Related compounds	Thiophosgene Formaldehyde Carbonic acid Urea Carbon monoxide Chloroformic acid Phosgene oxime
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