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Sigma-Aldrich

Chloroacetic anhydride

95%

Synonym(s):

Monochloroacetic acid anhydride

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About This Item

Linear Formula:
(ClCH2CO)2O
CAS Number:
541-88-8
Molecular Weight:
170.98
Beilstein:
774533
EC Number:
208-794-2
MDL number:
MFCD00000929
UNSPSC Code:
12352100
PubChem Substance ID:
24852874
NACRES:
NA.22

vapor pressure

<0.75 mmHg ( 20 °C)

Assay

95%

form

solid

bp

120-123 °C/20 mmHg (lit.)

mp

48-60 °C (lit.)

solubility

chloroform: soluble 100 mg/mL, clear, colorless to faintly yellow

SMILES string

ClCC(=O)OC(=O)CCl

InChI

1S/C4H4Cl2O3/c5-1-3(7)9-4(8)2-6/h1-2H2

InChI key

PNVPNXKRAUBJGW-UHFFFAOYSA-N

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Application

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 (D,L-7AW)
  • 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2′,1′:4,5]-2-oxazoline

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

289.4 °F - closed cup

Flash Point(C)

143 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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K L Matta et al.
Carbohydrate research, 51(2), 215-222 (1976-11-01)
The use of the chloroacetyl group as a protecting group has been studied for a 2-methylglyco-[2',1':4,5]-2-oxazoline. The reaction of chloroacetyl chloride or chloroacetic anhydride with 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-beta-D-glucopyranose provided 2-acetamido-1,3,4-tri-O-acetyl-6-O-(chloroacetyl)-2-deoxy-beta-D-glucopyranose which, on treatment with anhydrous ferric chloride in dichloromethane, produced the desired
J D Brennan et al.
Analytical biochemistry, 252(2), 260-270 (1997-11-05)
The reaction of D,L-7-azatryptophan (D,L-7AW) with tryptophanyl-tRNA synthetase (TrpRS), adenosine triphosphate (ATP), and Mg2+ in the presence of inorganic pyrophosphatase results in the formation of a highly fluorescent l-7AW-adenylate complex. Detection of this complex is based on its enhanced fluorescence
Darcy C Burns et al.
Nature protocols, 2(2), 251-258 (2007-04-05)
This protocol describes a procedure for the synthesis of 3,3'-bis(sulfonato)-4,4'-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive, photo-switchable cross-linker. In addition, a protocol is outlined for installing the cross-linker in an intramolecular fashion onto proteins bearing two surface-exposed Cys residues. BSBCA is designed

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