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215163

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

functional group

anhydride
chloro
ester

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0097
MKCV4192
MKCT3780
MKCQ8383
MKCQ6792

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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
Amandine Gendron et al.
Pharmaceutics, 13(1) (2021-01-16)
Cyclosporin A (CsA) is a molecule with well-known immunosuppressive properties. As it also acts on the opening of mitochondrial permeability transition pore (mPTP), CsA has been evaluated for ischemic heart diseases (IHD). However, its distribution throughout the body and its
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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