215163
Chloroacetic anhydride
95%
Synonym(s):
Monochloroacetic acid anhydride
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About This Item
Linear Formula:
(ClCH2CO)2O
CAS Number:
Molecular Weight:
170.98
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-794-2
Beilstein/REAXYS Number:
774533
MDL number:
Assay:
95%
Form:
solid
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
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
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B
Storage Class
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
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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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