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Phosgene information


"COCl2" redirects here. For the compound CoCl2, see Cobalt(II) chloride.
Not to be confused with phosphine, phosphene, oxalyl chloride, or phosgene oxime.
Phosgene[1]
Full structural formula with dimensions
Space-filling model

A sample case of toxic gases used in chemical warfare; the leftmost contains phosgene in a sealed capillary
Names
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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29365 checkY
ChemSpider
  • 6131 checkY
ECHA InfoCard 100.000.792 Edit this at Wikidata
EC Number
  • 200-870-3
PubChem CID
  • 6371
RTECS number
  • SY5600000
UNII
  • 117K140075 checkY
UN number 1076
CompTox Dashboard (EPA)
  • DTXSID0024260 Edit this at Wikidata
InChI
  • InChI=1S/CCl2O/c2-1(3)4 checkY
    Key: YGYAWVDWMABLBF-UHFFFAOYSA-N checkY
  • 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
 GHS04: Compressed GasGHS05: CorrosiveGHS06: Toxic[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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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]
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
[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).
checkY verify (what is checkY☒N ?)
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]

  1. ^ Merck Index, 11th Edition, 7310.
  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 (inactive 2024-05-09). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of May 2024 (link)
  3. ^ a b c d e 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.
  5. ^ a b c Record of Phosgene in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 16 March 2021.
  6. ^ a b "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
  8. ^ Wolfgang Schneider; Werner Diller. "Phosgene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_411. ISBN 978-3527306732.

and 28 Related for: Phosgene information

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Phosgene

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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...

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Phosgene oxime

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Phosgene oxime, or CX, is an organic compound with the formula Cl2C=N−OH. It is a potent chemical weapon, specifically a nettle agent. The compound itself...

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Chloroform

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from soil and surface water and undergoes degradation in air to produce phosgene, dichloromethane, formyl chloride, carbon monoxide, carbon dioxide, and...

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Chemical weapons in World War I

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ranged from disabling chemicals, such as tear gas, to lethal agents like phosgene, chlorine, and mustard gas. These chemical weapons caused medical problems...

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German phosgene attack of 19 December 1915

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The German phosgene attack of 19 December 1915 was the first use of phosgene gas against British troops by the German army. The gas attack took place...

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Bhopal disaster

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chemical process employed in the Bhopal plant had methylamine reacting with phosgene to form MIC, which was in turn reacted with 1-naphthol to form the final...

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Diphosgene

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Diphosgene is related to phosgene and has comparable toxicity, but is more conveniently handled because it is a liquid, whereas phosgene is a gas. Diphosgene...

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Polycarbonate

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polycarbonate material is produced by the reaction of bisphenol A (BPA) and phosgene COCl 2. The overall reaction can be written as follows: The first step...

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Chemical warfare

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industrial uses. Examples include phosgene and chloropicrin. Both have been used as chemical weapons but phosgene is an important precursor in the manufacture...

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Chemical weapon

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Widely used during the World War I, the effects of so-called mustard gas, phosgene gas, and others caused lung searing, blindness, death and maiming. During...

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Blister agent

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rendered obsolete with the development of British anti-Lewisite in the 1940s. Phosgene oxime – Occasionally included among the blister agents, although it is...

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Triphosgene

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compound with the formula OC(OCCl3)2. It is used as a solid substitute for phosgene, which is a gas and diphosgene, which is a liquid. Triphosgene is stable...

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PH helmet

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British Army in the First World War, to protect troops against chlorine, phosgene and tear gases. Rather than having a separate filter for removing the toxic...

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Carbon tetrachloride

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gives phosgene: CCl 4 + CO 2 ⟶ 2 COCl 2 {\displaystyle {\ce {CCl4 + CO2 -> 2COCl2}}} A similar reaction with carbon monoxide instead gives phosgene and...

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Oxalyl chloride

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hydrogen chloride HCl, which is subsequently degraded to oxalyl chloride and phosgene COCl2: C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HCl C2Cl4O2CO → C2O2Cl2 + COCl2...

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Asphyxia

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body Contact with certain chemicals, including pulmonary agents (such as phosgene) and blood agents (such as hydrogen cyanide) Drowning Drug overdose Exposure...

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Organic compound

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organic solvent). Halides of carbon without hydrogen (e.g., CF4 and CClF3), phosgene (COCl2), carboranes, metal carbonyls (e.g., nickel tetracarbonyl), mellitic...

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Acyl halide

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syntheses of acyl chlorides also entail the reaction of carboxylic acids with phosgene, thionyl chloride, and phosphorus trichloride Phosphorus pentabromide is...

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List of chemical warfare agents

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skin necrotizers and are known as the most painful substances produced. Phosgene oxime (CX) These substances are metabolic poisons that interfere with the...

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Pulmonary agent

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Chloropicrin (PS) Diphosgene (DP) Phosgene (CG) Disulfur decafluoride Perfluoroisobutene Acrolein Diphenylcyanoarsine Phosgene is the most dangerous commonly...

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Hexamethylenetetramine

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to phosgene in World War I. Subsequent studies have shown that large doses of hexamethylenetetramine provide some protection if taken before phosgene exposure...

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Benzyl chloroformate

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prepared in the lab by treating benzyl alcohol with phosgene: PhCH2OH + COCl2 → PhCH2OC(O)Cl + HCl Phosgene is used in excess to minimise the production of...

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Methyl chloroformate

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Methyl chloroformate can be synthesized using anhydrous methanol and phosgene. COCl2 + CH3OH → ClC(O)OCH3 + HCl Methyl chloroformate hydrolyzes in water...

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Acute inhalation injury

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usually from the release of acidic or alkaline radicals. Smoke, chlorine, phosgene, sulfur dioxide, hydrogen chloride, hydrogen sulfide, nitrogen dioxide...

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Boiling liquid expanding vapor explosion

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involved are toxic and do not catch fire upon release. Chlorine, ammonia and phosgene are example of toxic gases that underwent BLEVE in past accidents and produced...

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Atomic bombings of Hiroshima and Nagasaki

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assuredly can decrease the cost in American lives": poison gas. Quantities of phosgene, mustard gas, tear gas and cyanogen chloride were moved to Luzon from stockpiles...

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Moscow hostage crisis chemical agent

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Nitrogen mustard HN1 HN2 HN3 Phosgene oxime (CX) C01-A035 C01-A039 Nerve Pulmonary/choking Chlorine Chloropicrin (PS) Phosgene (CG) Diphosgene (DP) Disulfur...

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NFPA 704

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exposure could cause death or major residual injury (e.g. aluminum phosphide, hydrogen cyanide, phosgene, diborane, methyl isocyanate, hydrofluoric acid)...

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