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Chloroacetic anhydride has been used in the synthesis of 3,3?-bis(sulfonato)-4,4?-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive and photo-switchable cross-linker, D,L-7-azatryptophan, 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2?,1?:4,5]-2-oxazoline.
Darcy C Burns; Fuzhong Zhang; G Andrew Woolley. Synthesis of 3,3'-bis(sulfonato)-4,4'-bis(chloroacetamido)azobenzene and cysteine cross-linking for photo-control of protein conformation and activity. Nature Protocols. 2007, 2 (2), 251-258.
J D Brennan; C W Hogue; B Rajendran; K J Willis; A G Szabo. Preparation of enantiomerically pure L-7-azatryptophan by an enzymatic method and its application to the development of a fluorimetric activity assay for tryptophanyl-tRNA synthetase. Analytical Biochemistry. 1997, 252 (2), 260-270.
Has been used, in the presence of pyridine, for alcohol protection: J. Org. Chem., 35, 1940 (1970); cf Chloroacetyl chloride, A15846.
Hazard Statements: H300-H314-H318
Fatal if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Do not breathe dusts or mists. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.