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Sigma-Aldrich

Acetoxyacetyl chloride

97%

Synonym(s):

α-Acetoxyacetyl chloride, (Acetyloxy)acetyl chloride, (Chlorocarbonyl)methyl acetate, 2-(Acetyloxy)acetyl chloride, 2-Acetoxyacetyl chloride, 2-Chloro-2-oxoethyl acetate, Acetic acid (chlorocarbonyl)methyl ester, Acetylglycoloyl chloride

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About This Item

Linear Formula:
CH3CO2CH2COCl
CAS Number:
13831-31-7
Molecular Weight:
136.53
EC Number:
237-542-4
MDL number:
MFCD00011535
UNSPSC Code:
12352100
PubChem Substance ID:
24858248
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.428 (lit.)

bp

55 °C/12 mmHg (lit.)

density

1.27 g/mL at 25 °C (lit.)

SMILES string

CC(=O)OCC(Cl)=O

InChI

1S/C4H5ClO3/c1-3(6)8-2-4(5)7/h2H2,1H3

InChI key

HZDNNJABYXNPPV-UHFFFAOYSA-N

Application

Acetoxyacetyl chloride was used in synthesis of stabilized axial and equatorial conformers of spiro-β-lactams and glycolylhydroxamic acids.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

159.8 °F - closed cup

Flash Point(C)

71 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M D Corbett et al.
Chemical research in toxicology, 1(4), 222-227 (1988-07-01)
A new and improved method for the synthesis of glycolylhydroxamic acids is described. The two-step method involves acylation of arylhydroxylamines with acetoxyacetyl chloride, followed by saponification of the ester bond to give the desired products. The conversion of hydroxamic acids
Naveen Anand et al.
The Journal of organic chemistry, 76(15), 5999-6006 (2011-06-15)
The facile synthesis of the stabilized axial and equatorial conformers of spiro-β-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2]-cycloaddition reaction followed by their kinetic resolution. The immobilization of the racemic

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