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Trichloronitrosomethane

Names
Other names TL-358
Identifiers
CAS Number	3711-49-7
3D model (JSmol)	Interactive image
ChemSpider	69724
PubChem CID	77305
CompTox Dashboard (EPA)	DTXSID80190610
InChI InChI=1S/CCl3NO/c2-1(3,4)5-6Key: WXWITNRAXGTELB-UHFFFAOYSA-N
SMILES C(N=O)(Cl)(Cl)Cl
Properties
Chemical formula	CCl3NO
Molar mass	148.37 g·mol
Appearance	Deep blue liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Trichloronitrosomethane is a chlorinated nitrosoalkane. It is a deep blue liquid with powerful lachrymatory effects.

Synthesis

Trichloronitrosomethane can be produced with following methods:

• Oxidation of trichloromethylsulfinic acid with nitric acid.
• Reaction of sodium trichloromethylsulfinate with sodium nitrite and sodium nitrate or potassium nitrate in sulfuric acid.
• Pyrolysis of trichloroacethydroxamic acid.

Chemistry

Trichloronitrosomethane is an unstable substance. It slowly decomposes into nitrosyl chloride, nitrogen oxides, and chloropicrin over time.

Trichloronitrosomethane can be reduced to phosgene oxime by hydrogen sulfide.

See also

• Chloropicrin
• Trifluoronitrosomethane
• Phosgene oxime

References

1. ^ Sartori, Mario (1939). The War Gases. New York: D. Von Nostrand. pp. 164–165.
2. Sutcliffe, H. (September 1965). "The Synthesis of Trichloronitrosomethane". The Journal of Organic Chemistry. 30 (9): 3221–3222. doi:10.1021/jo01020a516.

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