2156. Chloropicrin

Nomenclature

CAS number: 76-06-2
Trichloronitromethane; acquinite; nitrochloroform; Larvacide 100; Picfume (Dow).
CCl3NO2; mol wt 164.38.
C 7.31%, Cl 64.70%, N 8.52%, O 19.47%.

Description and references

First prepd in 1848 by Stenhouse from picric acid and bleach powder. Review of prepn, properties, physiological action, and uses: Jackson, Chem. Rev. 14, 251 (1934). Manuf from nitromethane and alkaline hypochlorite: Wilhelm, US 3106588 (1963).

Properties

Slightly oily liquid, intense odor; bp757 112°. mp -64°; mp -69.2° (corr). d420 1.6558, d425 1.6483. nD20 1.4611, nD25 1.4596. Poisonous. Dipole moment in heptane or benzene, 1.80D. Practically insol in water. Soly in water (g/100 ml): 0.2272 (0°), 0.1621 (25°). Miscible with benzene, abs alc, carbon disulfide; sol in ether.

Caution

Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; lacrimation; cough, pulmonary edema; nausea, vomiting. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 66.

Use

Disinfecting cereals and grains; in synthesis, esp in manuf of methyl violet; fumigant; soil insecticide; war gas.