Trichloronitrosomethane

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)5-6 Key: WXWITNRAXGTELB-UHFFFAOYSA-N;
	SMILES C(N=O)(Cl)(Cl)Cl;
Properties
Chemical formula	CCl3NO
Molar mass	148.37 g·mol−1
Appearance	Deep blue liquid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trichloronitrosomethane is a chlorinated nitrosoalkane. It is a deep blue liquid with powerful lachrymatory effects.[1]

Synthesis

Trichloronitrosomethane can be produced with following methods:[1][2]

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.

Trichloronitrosomethane is an unstable substance. It slowly decomposes into nitrosyl chloride, nitrogen oxides, and chloropicrin over time.[1]

Trichloronitrosomethane can be reduced to phosgene oxime by hydrogen sulfide.[1]

Sartori, Mario (1939). The War Gases (PDF).
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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