Trichloronitrosomethane

Trichloronitrosomethane

Names
Other names TL-358
Identifiers
CAS Number	3711-49-7  Y
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.

Chemistry

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]

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.