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Thermo Scientific Chemicals
Chloroacetic anhydride, 97%
CAS: 541-88-8 | C4H4Cl2O3 | 170.97 g/mol
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化學識別
CAS541-88-8
IUPAC Name2-chloroacetyl 2-chloroacetate
Molecular FormulaC4H4Cl2O3
InChI KeyPNVPNXKRAUBJGW-UHFFFAOYSA-N
SMILESClCC(=O)OC(=O)CCl
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規格
規格表
規格表Appearance (Color)White to cream to brown
FormCrystals or powder or crystalline powder or fused solid
Assay (GC)≥94.0%
Identification (FTIR)Conforms
Melting Point (clear melt)50.0-61.0°C
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Freely soluble in ether, chloroform. Slightly soluble in benzene. Insoluble in cold ligroin
Notes
Moisture sensitive. Incompatible with oxidizing agent, bases, amines, alcohols, water/ moisture.
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.
Solubility
Freely soluble in ether, chloroform. Slightly soluble in benzene. Insoluble in cold ligroin
Notes
Moisture sensitive. Incompatible with oxidizing agent, bases, amines, alcohols, water/ moisture.
RUO – Research Use Only
General References:
- 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.