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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: H301-H311-H314-H331-H335
Toxic if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. Toxic if inhaled. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant