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Acetoxyacetyl chloride
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Name

Acetoxyacetyl chloride

 EINECS 237-542-4
CAS No. 13831-31-7 Density 1.281 g/cm3
PSA 43.37000 LogP 0.31490
Solubility Reacts with water violently. Melting Point 159-160 °C
Formula C4H5ClO3 Boiling Point 163.7 °C at 760 mmHg
Molecular Weight 136.535 Flash Point 62.5 °C
Transport Information UN 3265 8/PG 2 Appearance Clear colorless to pale yellow liquid
Safety 23-26-27-36/37/39-45-8 Risk Codes 14-34-36/37
Molecular Structure Molecular Structure of 13831-31-7 (Acetoxyacetyl chloride) Hazard Symbols CorrosiveC
Synonyms

Acetylchloride, (acetyloxy)- (9CI);Glycoloyl chloride, acetate (6CI,8CI);(Acetyloxy)acetyl chloride;2-Acetoxyacetyl chloride;2-Chloro-2-oxoethylacetate;Acetic acid (chlorocarbonyl)methyl ester;Acetylchloride, 2-(acetyloxy)-;a-Acetoxyacetyl chloride;

Article Data 23

Acetoxyacetyl chloride Synthetic route

13831-30-6

acetoxyacetic acid

13831-31-7

Acetoxyacetyl chloride

Conditions
ConditionsYield
With thionyl chloride; acetyl chloride for 1.3h; Heating;77.5%
With phosphorus trichloride
With thionyl chloride; acetyl chloride
79-14-1

glycolic Acid

75-36-5

acetyl chloride

13831-31-7

Acetoxyacetyl chloride

Conditions
ConditionsYield
With pyridine Behandeln des vom Acetylchlorid befreiten Reaktionsgemisches mit Thionylchlorid und wenig Pyridin;
(i), (ii) PCl3; Multistep reaction;
(i), (ii) SOCl2; Multistep reaction;
With thionyl chloride
79-14-1

glycolic Acid

108-24-7

acetic anhydride

13831-31-7

Acetoxyacetyl chloride

Conditions
ConditionsYield
(i) H2SO4, (ii) SOCl2; Multistep reaction;
180048-73-1

2-hydroxy-2-methyl-1-(4-(methylsulfonyl)-phenyl)propan-1-one

13831-31-7

Acetoxyacetyl chloride

acetoxy-acetic acid 2-(4-methanesulfonylphenyl)-1,1-dimethyl-2-oxo-ethyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 20℃; Solvent;100%
With dmap; triethylamine In dichloromethane at 0℃;99.5%
With pyridine In acetonitrile
With triethylamine In dichloromethane at 20℃; for 3h; Solvent; Reagent/catalyst;207 g
With triethylamine In dichloromethane at 20℃; for 4h; Solvent; Reagent/catalyst;220 g
615-36-1

2-bromoaniline

13831-31-7

Acetoxyacetyl chloride

901335-15-7

acetic acid (2-bromo-phenylcarbamoyl)-methyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h;100%
With pyridine In dichloromethane at 20℃; for 2h;

C36H43FN2O4

13831-31-7

Acetoxyacetyl chloride

C40H47FN2O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;100%
367-24-8

4-bromo-2-fluoroaniline

13831-31-7

Acetoxyacetyl chloride

2-((4-bromo-2-fluorophenyl)amino)-2-oxoethyl acetate

Conditions
ConditionsYield
In chloroform at 20℃; for 0.5h; Inert atmosphere;100%
In chloroform at 20℃; Inert atmosphere;100%
With potassium carbonate In chloroform75%
In chloroform at 20℃; for 0.5h; Inert atmosphere;
653600-07-8

(cis)-3-(4-fluoro-phenoxy)-8-aza-bicyclo[3.2.1]octane

13831-31-7

Acetoxyacetyl chloride

acetic acid 2-[(cis)-3-(4-fluoro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-2-oxo-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;100%
862682-63-1

2-[4-(piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

13831-31-7

Acetoxyacetyl chloride

2-{4-[4-(2-acetoxyacetyl)piperazin-1-yl]amino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 18 - 25℃; for 1.25h;100%
417727-43-6

3-(4-fluoro-benzyl)-3,8-diaza-bicyclo[3.2.1]octane

13831-31-7

Acetoxyacetyl chloride

acetic acid 2-[3-(4-fluoro-benzyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-2-oxo-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane100%

Acetoxyacetyl chloride Chemical Properties

Structure of Acetoxyacetyl chloride (CAS NO.13831-31-7):

IUPAC Name: (2-chloro-2-oxoethyl) acetate 
Empirical Formula: C4H5ClO3
Molecular Weight: 136.5337 
EINECS: 237-542-4 
Index of Refraction: 1.424
Molar Refractivity: 27.23 cm3
Molar Volume: 106.5 cm3
Polarizability: 10.79×10-24cm3
Surface Tension: 35.2 dyne/cm
Density: 1.281 g/cm3
Flash Point: 62.5 °C
Enthalpy of Vaporization: 40.03 kJ/mol
Boiling Point: 163.7 °C at 760 mmHg
Vapour Pressure: 2.04 mmHg at 25°C 
Physical Appearance: Clear colorless to pale yellow liquid
Product Categories: Biochemistry;Reagents for Oligosaccharide Synthesis;Acid Halides;Carbonyl Compounds;Organic Building Blocks 
Synonyms of Acetoxyacetyl chloride (CAS NO.13831-31-7): 2-Chloro-2-oxoethyl acetate ; Acetyl chloride, 2-(acetyloxy) ; 2-Acetoxyacetyl chloride .
Canonical SMILES: CC(=O)OCC(=O)Cl
InChI: InChI=1S/C4H5ClO3/c1-3(6)8-2-4(5)7/h2H2,1H3
InChIKey: HZDNNJABYXNPPV-UHFFFAOYSA-N

Acetoxyacetyl chloride Safety Profile

Hazard Codes: CorrosiveC
Risk Statements: 14-34-36/37 
R14 :Reacts violently with water. 
R34:Causes burns. 
R36/37:Irritating to eyes and respiratory system.
Safety Statements: 23-26-27-36/37/39-45-8 
S23:Do not breathe vapour. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S8:Keep container dry.
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
Hazard Note: Corrosive
HazardClass: 8
PackingGroup: II

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