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302368

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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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
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

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