Chlorobenzalmalondinitrile

Chlorobenzalmalonodinitrile was synthesized at Middlebridge College by two Americans, Ben Corson, and Roger Stoughton, in 1928. It is believed that the designation CS comes from the first letters of the names of the discoverers.

CS is a colorless, non-volatile crystalline substance with the smell of pepper. Melting point 95 ° C; boiling point 310-315 ° C. It is poorly soluble in water (0.01% at 30 ° C), moderately in alcohol, good in acetone, chloroform. The substance is chemically stable; it hydrolyzes very slowly with water to form o-chlorobenzaldehyde and malonodinitrile. In 95% ethanol, the hydrolysis time is 99% at 30 ° C for 635 minutes, at 40 ° C - 265 minutes. Diluted alkalis accelerate hydrolysis, acids slow it down. Chlorobenzalmalonodinitrile reacts with oxidizing agents with a loss of irritating properties. Thermally stable up to 300 ° C, decomposes at 625 ° C in 15-20 s.

Chlorobenzalmalonodinitrile is obtained by the reaction reverse to hydrolysis in the presence of bases ( Knevenagel reaction ):

The combat condition is aerosol. It is used with the help of chemical aerial bombs, artillery shells, aerosol generators and smoke grenades. CS in small concentrations is irritating to the eyes and upper respiratory tract, and in high concentrations it causes burns to exposed skin, in some cases - respiratory paralysis, heart and death. Signs of damage: severe burning and pain in the eyes and chest, severe lacrimation, involuntary closing of the eyelids, sneezing, runny nose (sometimes with blood), painful burning in the mouth, nasopharynx, upper respiratory tract, cough and chest pain. Upon exiting the infected atmosphere or after putting on a gas mask, symptoms continue to increase for 15 to 20 minutes, and then gradually subside over 1 to 3 hours. Protection against CS - gas mask, skin protection products are sometimes required.

Intolerable concentration in the air 0.001-0.005 mg / l (1 min). A striking concentration of 5 mg / m³. Intolerable toxic dose of 0.02 g · min / m³. Mid-lethal toxic dose (LCt ₅₀ ) 25 g · min / m³. The damaging effect on the skin is twice as strong as that of chloroacetophenone and bromobenzyl cyanide .

It is used by law enforcement to disperse demonstrations and eliminate street riots, as well as in gas self-defense weapons: gas cartridges , cartridges for gas pistols and revolvers.

• Chemical weapon
• Dibenzoxazepine

• N. S. Zefirov - Chemical Encyclopedia vol. 5: Great Russian Encyclopedia: 1999
• Kenneth Barbalace. Chemical Database - Tert-tetradecyl mercaptan EnvironmentalChemistry.com. Date of treatment October 16, 2010.