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302341

Sigma-Aldrich

Acetoxyacetic acid

99%

Synonym(s):

α-Acetoxyacetic acid, (Acetyloxy)acetic acid, 2-(Acetyloxy)acetic acid, 2-Hydroxyacetic acid acetate, Acetylglycolic acid, O-Acetylglycolic acid

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About This Item

Linear Formula:
CH3CO2CH2CO2H
CAS Number:
13831-30-6
Molecular Weight:
118.09
EC Number:
237-541-9
MDL number:
MFCD00011551
UNSPSC Code:
12352100
PubChem Substance ID:
24858247
NACRES:
NA.22

Assay

99%

bp

141-142 °C/12 mmHg (lit.)

mp

67-69 °C (lit.)

SMILES string

CC(=O)OCC(O)=O

InChI

1S/C4H6O4/c1-3(5)8-2-4(6)7/h2H2,1H3,(H,6,7)

InChI key

MLXDUYUQINCFFV-UHFFFAOYSA-N

General description

Acetoxyacetic acid is kinetically stable degradation product of oxidative degradation of 1,3-dialkylimidazolium ionic liquids in hydrogen peroxide/aceticacid aqueous medium assisted by ultrasonic chemical irradiation. It is an intermediate formed during reactions of manganic acetate in glacial acetic acid with benzene (100°C), chlorobenzene, or toluene.

Application

Acetoxyacetic acid was used in preparation of tert-butyl glycolate.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Xuehui Li et al.
Dalton transactions (Cambridge, England : 2003), (19)(19), 1875-1880 (2007-08-19)
A highly efficient process for oxidative degradation of 1,3-dialkylimidazolium ionic liquids in hydrogen peroxide/acetic acid aqueous medium assisted by ultrasonic chemical irradiation is, for the first time, described. It is shown that more than 93% of the 1,3-dialkylimidazolium cation with
Synthetic studies of pyridomycin. II. Synthesis of a model twelve-membered ring compound related to pyridomycin.
Kinoshita M and Awamura M.
Bulletin of the Chemical Society of Japan, 51(3), 869-871 (1978)
Intermediate steps in autoxidation: III. Reactions of MnIII acetate in acetic acid with benzene, chlorobenzene, and toluene.
Van der PRE, et al.
J. Catal., 10(1), 52-59 (1968)
Amberlyn M Wands et al.
ACS infectious diseases, 4(5), 758-770 (2018-02-08)
Cholera toxin (CT) enters host intestinal epithelia cells, and its retrograde transport to the cytosol results in the massive loss of fluids and electrolytes associated with severe dehydration. To initiate this intoxication process, the B subunit of CT (CTB) first

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