13831-31-7

Basic information

• Product Name: Acetoxyacetyl chloride
• Synonyms: ACETOXYACETYL CHLORIDE;2-ACETOXYACETYL CHLORIDE;2-chloro-2-oxoethyl acetate;(Acetyloxy)acetyl chloride;Acetoxyacetic acid chloride;Acetoxyacetyl chloride,97%;acetyl chloride, (acetyloxy)-;Acetoxyacetyl chloride ,98%
• CAS NO: 13831-31-7
• Molecular Formula: C₄H₅ClO₃
• Molecular Weight: 136.53
• EINECS: 237-542-4
• Product Categories: Biochemistry;Reagents for Oligosaccharide Synthesis;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 13831-31-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 159-160 °C
• Boiling Point: 55 °C12 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.27 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.04mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: water-free area
• Water Solubility: Reacts with water violently.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Acetoxyacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Acetoxyacetyl chloride(13831-31-7)
• EPA Substance Registry System: Acetoxyacetyl chloride(13831-31-7)

Safety Data

• Hazard Codes: C
• Statements: 14-34-36/37
• Safety Statements: 23-26-27-36/37/39-45-8
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: N
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13831-31-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

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

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

Synthetic route

acetoxyacetic acid (13831-30-6) → Acetoxyacetyl chloride (13831-31-7)

Conditions	Yield
With thionyl chloride; acetyl chloride for 1.3h; Heating;	77.5%
With phosphorus trichloride
With thionyl chloride; acetyl chloride

glycolic Acid (79-14-1) + acetyl chloride (75-36-5) → Acetoxyacetyl chloride (13831-31-7)

Conditions	Yield
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

glycolic Acid (79-14-1) + acetic anhydride (108-24-7) → Acetoxyacetyl chloride (13831-31-7)

Conditions	Yield
(i) H2SO4, (ii) SOCl2; Multistep reaction;

2-hydroxy-2-methyl-1-(4-(methylsulfonyl)-phenyl)propan-1-one (180048-73-1) + Acetoxyacetyl chloride (13831-31-7) → acetoxy-acetic acid 2-(4-methanesulfonylphenyl)-1,1-dimethyl-2-oxo-ethyl ester

Conditions	Yield
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

2-bromoaniline (615-36-1) + Acetoxyacetyl chloride (13831-31-7) → acetic acid (2-bromo-phenylcarbamoyl)-methyl ester (901335-15-7)

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

C36H43FN2O4 + Acetoxyacetyl chloride (13831-31-7) → C40H47FN2O7

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;	100%

4-bromo-2-fluoroaniline (367-24-8) + Acetoxyacetyl chloride (13831-31-7) → 2-((4-bromo-2-fluorophenyl)amino)-2-oxoethyl acetate

Conditions	Yield
In chloroform at 20℃; for 0.5h; Inert atmosphere;	100%
In chloroform at 20℃; Inert atmosphere;	100%
With potassium carbonate In chloroform	75%
In chloroform at 20℃; for 0.5h; Inert atmosphere;

(cis)-3-(4-fluoro-phenoxy)-8-aza-bicyclo[3.2.1]octane (653600-07-8) + Acetoxyacetyl chloride (13831-31-7) → acetic acid 2-[(cis)-3-(4-fluoro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-2-oxo-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%

2-[4-(piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (862682-63-1) + Acetoxyacetyl chloride (13831-31-7) → 2-{4-[4-(2-acetoxyacetyl)piperazin-1-yl]amino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Conditions	Yield
With triethylamine In dichloromethane at 18 - 25℃; for 1.25h;	100%

3-(4-fluoro-benzyl)-3,8-diaza-bicyclo[3.2.1]octane (417727-43-6) + Acetoxyacetyl chloride (13831-31-7) → acetic acid 2-[3-(4-fluoro-benzyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-2-oxo-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane	100%

methyl 2-(6-(3-(8-azabicyclo[3.2.1]octan-3-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)acetate (1065608-29-8) + Acetoxyacetyl chloride (13831-31-7) → 2-(3-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-oxoethyl acetate (1065608-34-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.0833333h;	100%

5(S)-(isoxazol-3-ylaminomethyl)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one trifluoroacetate (264600-27-3) + Acetoxyacetyl chloride (13831-31-7) → 5(S)-(isoxazol-3-ylaminomethyl)-3-(4-(1-acetoxyacetyl-1,2,5,6-tetrahydropyrid-4yl)phenyl)oxazolidin-2-one

Conditions	Yield
Stage #1: 5(S)-(isoxazol-3-ylaminomethyl)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one trifluoroacetate With sodium hydrogencarbonate In water; acetone at 0 - 4℃; Stage #2: Acetoxyacetyl chloride In water; acetone at 0 - 5℃; for 0.333333h;	100%

Acetoxyacetyl chloride (13831-31-7) + 3-((E)-3-{4-[1-(t-butoxycarbonyl)piperidin-4-yloxy]phenylamino}-1-propenyl)benzonitrile (337519-98-9) → C30H35N3O6 (475504-77-9)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	100%

C36H60N6S2 + Acetoxyacetyl chloride (13831-31-7) → C52H76N6O12S2 (1185199-11-4)

Conditions	Yield
With triethylamine	100%

(((CH3)3C)C6H2CH2NHCH2CH2NHCH2CH2NHCH2)2(SCH2CH2S) (366804-69-5) + Acetoxyacetyl chloride (13831-31-7) → C58H80N6O18S2 (1185199-09-0)

Conditions	Yield
With triethylamine	100%

3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine hydrochloride + Acetoxyacetyl chloride (13831-31-7) → acetic acid 2-[4-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-piperidin-1-yl]-2-oxo-ethyl ester

Conditions	Yield
Stage #1: 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: Acetoxyacetyl chloride In dichloromethane at 0 - 20℃; for 1h;	100%
Stage #1: 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: Acetoxyacetyl chloride In dichloromethane at 20℃; for 1h;	100%

(2,4-dimethoxybenzyl)-(3-methoxyphenyl)amine (1020936-75-7) + Acetoxyacetyl chloride (13831-31-7) → 2-acetoxy-N-(2,4-dimethoxybenzyl)-N-(3-methoxyphenyl)acetamide (1318074-43-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

4,4-bis-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)piperidine-1-carboxylic acid ethyl ester (1402049-10-8) + Acetoxyacetyl chloride (13831-31-7) → acetic acid 2-[4,4-bis-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)piperidin-1-yl]-2-oxo-ethyl ester (1402049-43-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 3h;	100%

(5-(5-(aminomethyl)-1,3,4-oxadiazol-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)(3-bromophenyl)methanone + Acetoxyacetyl chloride (13831-31-7) → 2-(((5-(4-(3-bromobenzoyl)-3,5-dimethyl-1H-pyrrol-2-yl)-1,3,4-oxadiazol-2-yl)methyl)amino)-2-oxoethyl acetate

Conditions	Yield
With triethylamine In dichloromethane	100%

p-aminoiodobenzene (540-37-4) + Acetoxyacetyl chloride (13831-31-7) → 2-((4-iodophenyl)amino)-2-oxoethyl acetate

Conditions	Yield
In dichloromethane at 20℃; for 1.75h;	100%

4-bromodeacetyl colchicine + Acetoxyacetyl chloride (13831-31-7) → N-(acetoxyacetyl)-4-bromodeacetyl colchicine

Conditions	Yield
In dichloromethane at 20℃; for 2h;	100%

[1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (131613-92-8) + Acetoxyacetyl chloride (13831-31-7) → C17H21NO6

Conditions	Yield
With 4-methyl-morpholine In chlorobenzene Microwave irradiation;	100%
With 4-methyl-morpholine Microwave irradiation; stereoselective reaction;	85%

N'-((1R,1'R,3r,3'R,5S,5'S)-[3,9'-bi(9'-azabicyclo[3.3.1]nonan)]-3'-yl)benzene-1,2-diamine (1126795-15-0) + Acetoxyacetyl chloride (13831-31-7) → 2-((2-((1R,1'R,3r,3'R,5S,5'S)-[3,9'-bi(9'-azabicyclo[3.3.1]nonan)]-3'-ylamino)phenyl)amino)-2-oxoethyl acetate (1616764-56-7)

Conditions	Yield
In dichloromethane for 0.5h; Cooling with ice;	99.5%

4-nitro-3-piperidin-1-yl-phenylamine (202279-91-2) + Acetoxyacetyl chloride (13831-31-7) → C15H19N3O5 (885705-21-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;	99%

5-amino-2,4,6-triiodoisophthalic acid dichloride (37441-29-5) + Acetoxyacetyl chloride (13831-31-7) → 2-((3,5-bis (chlorocarbonyl)-2,4,6-triiodophenyl)amino)-2-oxoethyl acetate (78314-12-2)

Conditions	Yield
In water	99%
In N,N-dimethyl acetamide at 20℃; for 15h; Cooling;	92%
In tetrahydrofuran; n-heptane at 20℃; Product distribution / selectivity; Heating / reflux;	35%

C11H13NO2 (1214742-74-1) + Acetoxyacetyl chloride (13831-31-7) → C15H17NO5 (1214742-73-0)

Conditions	Yield
With triethylamine In methanol at 0℃;	99%

C11H15NO2 (1214742-67-2) + Acetoxyacetyl chloride (13831-31-7) → C15H19NO5 (1214742-66-1)

Conditions	Yield
With triethylamine In methanol at 0℃;	99%

C17H31NO2Si (1253282-61-9) + Acetoxyacetyl chloride (13831-31-7) → C21H35NO5Si (1253282-62-0)

Conditions	Yield
With triethylamine In methanol; diethyl ether at 0 - 20℃;	99%

5-amino-N,N'-bis[2,3-bis(acetyloxy)propyl]2,4,6-triiodo-1,3-benzenedicarboxamide (76801-94-0) + Acetoxyacetyl chloride (13831-31-7) → 5-(acetoxyacetylamino)-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 4h;	99%

(S,E)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)but-3-en-1-amine + Acetoxyacetyl chloride (13831-31-7) → (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(3-butenyl)-2-azetidinone (358973-75-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h; Staudinger reaction;	98%

5(R)(N-isoxazol-3-yl-N-(tertbutoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one hydrochloride (264600-99-9) + Acetoxyacetyl chloride (13831-31-7) → 5(R)-(N-isoxazol-3-yl-N-(tertbutoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(1-acetoxyacetyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 0 - 20℃; for 2h;	98%

N-(4-hydroxybutyl)-O-benzyl-hydroxylamine (1253282-56-2) + Acetoxyacetyl chloride (13831-31-7) → C15H21NO5 (1253282-57-3)

Conditions	Yield
With triethylamine In methanol; diethyl ether at 0 - 20℃;	98%

5-(benzyloxy)-3,4,6-trimethylpyridine-2-amine (1444335-07-2) + Acetoxyacetyl chloride (13831-31-7) → 2-((5-benzyloxy-3,4,6-trimethylpyridin-2-yl)amino)-2-oxoethyl acetate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	98%

Upstream product

• 13831-30-6 acetoxyacetic acid 
• 79-14-1 glycolic Acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 408329-20-4 4-acetoxyacetyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 83-16-9 acetoxy-acetic acid-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamide) 
• 52762-38-6 2-(acetoxyacetyl)cyclohexanone 
• 5628-00-2 5-Chlor-2-acetoxyacetamino-benzophenon 
• 131968-76-8 (+/-)-(3R,4S)-3-acetoxy-N-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 87265-98-3 6-acetoxyacetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone 
• 135386-75-3 N-Benzoyl-N-butylacetoxyacetamide 
• 103174-02-3 (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 135508-49-5 (3S,4R)-3-acetoxy-4-<(R)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl>-1-(4-methoxyphenyl)azetidin-2-one 
• 133464-15-0 benzyl (S)-5-acetoxy-2-<(tert-butoxycarbonyl)amino>-4-oxopentanoate 
• 74280-94-7 3β-(Acetoxyacetamido)-1-<1-((benzyloxy)carbonyl)-2-methylprop-1-enyl>-4β-(methylthio)azetidin-2-one 
• 78032-29-8 acetonyl 2-(4'-acetoxyacetylthio-3'-ethyl-2'-oxoazetidin-1'-yl)-2-(triphenylphosphoranylidene)acetate 
• 136778-96-6 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3S,4R)-3-<(3'S,4'R)-3'-acetoxy-2'-oxo-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one 
• 98380-58-6 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3S,4R)-3-<(3'R,4'S)-3'-acetoxy-2'-oxo-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one 

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