Phosgene oxime

Source: Wikipedia, the free encyclopedia.
Phosgene oxime
Full structural formula
Space-filling model
  Carbon, C
  Hydrogen, H
  Oxygen, O
  Nitrogen, N
  Chlorine, Cl
Names
Preferred IUPAC name
1,1-Dichloro-N-hydroxymethanimine
Other names
  • CX
  • Dichloroformaldehyde oxime
  • Dichloroformaldoxime
  • Dichloroformoxime
  • Hydroxycarbonimidic dichloride
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/CHCl2NO/c2-1(3)4-5/h5H checkY
    Key: JIRJHEXNDQBKRZ-UHFFFAOYSA-N checkY
  • InChI=1/CHCl2NO/c2-1(3)4-5/h5H
    Key: JIRJHEXNDQBKRZ-UHFFFAOYAP
  • Cl/C(Cl)=N\O
Properties
Cl2CNOH
Molar mass 113.93 g·mol−1
Appearance colorless or white solid
Odor Strong, disagreeable and irritating
Melting point 35 to 40 °C (95 to 104 °F; 308 to 313 K)[1]
Boiling point 128 °C (262 °F; 401 K)[1]
70%[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
Related compounds
Related compounds
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 ?)

Phosgene oxime, or CX, is an organic compound with the formula Cl2C=NOH. It is a potent chemical weapon, specifically a nettle agent, which is a type of blister agent. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disagreeable and irritating odor. It is used as a reagent in organic chemistry.[2]

Preparation and reactions

Phosgene oxime can be prepared by

active hydrogen reducing agent
:

Cl3CNO2 + 4 [H] → Cl2C=N−OH + HCl + H2O

The observation of a transient violet color in the reaction suggests intermediate formation of trichloronitrosomethane (Cl3CNO). Early preparations, using stannous chloride as the reductant, also started with chloropicrin.[3]

The compound is

nucleophiles, including bases
, which destroy it:

Cl2CNOH + 2 NaOHCO2 + NH2OH + 2 NaCl + H2O

Phosgene oxime has been used to prepare heterocycles that contain N-O bonds, such as isoxazoles.[4]

nitrile oxide:[5]

Cl2CNOH → Cl−C≡N+−O + HCl

Toxicity

Phosgene oxime is classified as a

toxic
by inhalation, ingestion, or skin contact. The effects of the poisoning occur almost immediately. No antidote for phosgene oxime poisoning is known. Generally, any treatment is supportive. Typical physical symptoms of CX exposure are as follows:

References

External links