Product Name

  • Name

    Acetyl chloride, cyano-

  • EINECS
  • CAS No. 16130-58-8
  • Article Data63
  • CAS DataBase
  • Density 1.2170 (rough estimate)
  • Solubility
  • Melting Point
  • Formula C3H2 Cl N O
  • Boiling Point 73-75 °C
  • Molecular Weight 103.508
  • Flash Point
  • Transport Information
  • Appearance
  • Safety A poison. A storage hazard. It may explode at room temperature. Upon decomposition it emits toxic fumes of Cl−, NOx, and CN−. See also CYANIDE and CHLORIDES.
  • Risk Codes  3:;
  • Molecular Structure Molecular Structure of 16130-58-8 (Acetyl chloride, cyano-)
  • Hazard Symbols 3
  • Synonyms Cyanoacetic acid chloride;Cyanoacetyl chloride;Acetylchloride, cyano- (8CI,9CI);2-cyanoacetyl chloride;cyanoacetyl chloride;
  • PSA 40.86000
  • LogP 0.66548

Synthetic route

cyanoacetic acid
372-09-8

cyanoacetic acid

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h; Solvent; Temperature; Inert atmosphere;100%
With phosphorus pentachloride In diethyl ether at 20℃;89%
With phosphorus pentachloride In diethyl ether Inert atmosphere; Cooling with ice;52%
oxalyl dichloride
79-37-8

oxalyl dichloride

cyanoacetic acid
372-09-8

cyanoacetic acid

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2.5h;
cyanoacetic acid
372-09-8

cyanoacetic acid

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25℃; for 1h; Inert atmosphere;
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

cis-1-<1-<(tert-Butyldimethylsiloxy)methyl>-2-hydroxy-4-methyl-3-cyclohexenyl>-1-ethanone
75233-82-8

cis-1-<1-<(tert-Butyldimethylsiloxy)methyl>-2-hydroxy-4-methyl-3-cyclohexenyl>-1-ethanone

Cyano-acetic acid (1R,6R)-6-acetyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-2-enyl ester
75247-62-0

Cyano-acetic acid (1R,6R)-6-acetyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-2-enyl ester

Conditions
ConditionsYield
With pyridine In diethyl ether; dichloromethane at 0℃; for 0.25h;100%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

5-bromo-2-aminobenzoic acid methyl ester
52727-57-8

5-bromo-2-aminobenzoic acid methyl ester

methyl 2-(2-cyanoacetamido)-5-bromobenzoate
1179347-38-6

methyl 2-(2-cyanoacetamido)-5-bromobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
2-amino-4-(2-phenyl-cyclopropyl)-thiophene-3-carboxylic acid ethyl ester
844501-14-0

2-amino-4-(2-phenyl-cyclopropyl)-thiophene-3-carboxylic acid ethyl ester

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

2-(2-cyano-acetylamino)-4-(2-phenyl-cyclopropyl)-thiophene-3-carboxylic acid ethyl ester
844501-16-2

2-(2-cyano-acetylamino)-4-(2-phenyl-cyclopropyl)-thiophene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
In dichloromethane99%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C17H19NO3

C17H19NO3

C20H18N2O3

C20H18N2O3

Conditions
ConditionsYield
In benzene at 80℃; for 24h; Inert atmosphere;98%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C16H16BrNO2

C16H16BrNO2

C19H15BrN2O2

C19H15BrN2O2

Conditions
ConditionsYield
In benzene at 80℃; for 24h; Inert atmosphere;98%
1-[5-chloro-2-(4-methoxy-benzylamino)-phenyl]-ethanone
685540-89-0

1-[5-chloro-2-(4-methoxy-benzylamino)-phenyl]-ethanone

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C19H15ClN2O2

C19H15ClN2O2

Conditions
ConditionsYield
In benzene at 80℃; for 24h; Inert atmosphere;97%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

1-(2-((4-methoxybenzyl)amino)phenyl)propan-1-one

1-(2-((4-methoxybenzyl)amino)phenyl)propan-1-one

3-cyano-4-ethyl-2-quinolone

3-cyano-4-ethyl-2-quinolone

Conditions
ConditionsYield
In benzene at 80℃; for 12h; Inert atmosphere;97%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

(2R,5R)-2,5-Bis(methoxymethoxymethyl)pyrrolidine
90290-06-5

(2R,5R)-2,5-Bis(methoxymethoxymethyl)pyrrolidine

(2R,5R)-N-cyanoacetyl-2,5-bis(meyhoxymethoxymethyl)pyrrolidine
108138-88-1

(2R,5R)-N-cyanoacetyl-2,5-bis(meyhoxymethoxymethyl)pyrrolidine

Conditions
ConditionsYield
In dichloromethane Ambient temperature;96%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Cyano-acetic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester
132640-93-8

Cyano-acetic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester

Conditions
ConditionsYield
With silver cyanide In toluene at 80℃; for 4h;96%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

(-)-menthol
2216-51-5

(-)-menthol

(1R,2S,5R)-cyanoacetic acid 2-isopropyl-5-methylcyclohexyl ester
54082-39-2

(1R,2S,5R)-cyanoacetic acid 2-isopropyl-5-methylcyclohexyl ester

Conditions
ConditionsYield
With silver cyanide In toluene at 80℃; for 4h;95%
With N,N-dimethyl-aniline In diethyl ether
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

2,5-dimethoxyaniline
102-56-7

2,5-dimethoxyaniline

2,5-dimethoxy-cyanoacetanilide
113604-07-2

2,5-dimethoxy-cyanoacetanilide

Conditions
ConditionsYield
With triethylamine In dichloromethane95%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

N,N-Dicyclohexyl-C-((1R,2R,4S)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide
501445-38-1

N,N-Dicyclohexyl-C-((1R,2R,4S)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide

Cyano-acetic acid (1R,2R,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
132640-89-2

Cyano-acetic acid (1R,2R,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Conditions
ConditionsYield
With silver cyanide In toluene at 80℃; for 4h;93%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Cyano-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
132640-90-5

Cyano-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
ConditionsYield
With silver cyanide In toluene at 80℃; for 4h;92%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C8H14N2O2

C8H14N2O2

C10H15N3O2

C10H15N3O2

Conditions
ConditionsYield
Stage #1: C8H14N2O2 With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 20 - 30℃; for 0.5h;
Stage #2: cyanoacetic acid chloride In pyridine; dichloromethane at 20 - 30℃; for 10h; Concentration;		92%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C17H19NO2

C17H19NO2

C20H18N2O2

C20H18N2O2

Conditions
ConditionsYield
In benzene at 80℃; for 24h; Inert atmosphere;91%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

4-heptadecafluorooctylaniline
83766-52-3

4-heptadecafluorooctylaniline

C17H7F17N2O

C17H7F17N2O

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;91%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

N-(R-2-chloro-propyl)-2-aminoacetic acid tertbutyl ester

N-(R-2-chloro-propyl)-2-aminoacetic acid tertbutyl ester

tert-butyl 2-{N-[(2R)-2-chloropropyl]-2-cyanoacetamido}acetate

tert-butyl 2-{N-[(2R)-2-chloropropyl]-2-cyanoacetamido}acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 30 - 35℃; for 4h;90.5%
With triethylamine In dichloromethane at 30 - 35℃; for 4h;90.5%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

N-(R-2-chloropropyl)-2-aminoacetamide

N-(R-2-chloropropyl)-2-aminoacetamide

N-(R-2-chloropropyl)-N-(2-acetamido)-2-cyanoacetamide

N-(R-2-chloropropyl)-N-(2-acetamido)-2-cyanoacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 30 - 35℃; for 4h;89.1%
2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

3-(2,5-dimethyl-thiophen-3-yl)-3-oxo-propionitrile
608522-55-0

3-(2,5-dimethyl-thiophen-3-yl)-3-oxo-propionitrile

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 0℃; for 1h;89%
1-[5-chloro-2-(4-methoxy-benzylamino)-phenyl]-pentan-1-one
903594-22-9

1-[5-chloro-2-(4-methoxy-benzylamino)-phenyl]-pentan-1-one

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

4-butyl-6-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile
903594-66-1

4-butyl-6-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Conditions
ConditionsYield
In benzene at 80℃; for 2h;89%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C17H19NO2

C17H19NO2

C20H18N2O2

C20H18N2O2

Conditions
ConditionsYield
In benzene at 80℃; for 24h; Inert atmosphere;88%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

2-isopropylaniline
643-28-7

2-isopropylaniline

2-cyano-N-[2-(isopropyl)phenyl]acetamide
87165-41-1

2-cyano-N-[2-(isopropyl)phenyl]acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;88%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

2-((R)-2-chloropropylamino)-N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)acetamide

2-((R)-2-chloropropylamino)-N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)acetamide

C14H15ClN6O2

C14H15ClN6O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 40 - 45℃; for 6h;87.2%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

methyl 3-amino-3-(4-butoxyphenyl)butanoate
1441058-80-5

methyl 3-amino-3-(4-butoxyphenyl)butanoate

methyl 3-(4-butoxyphenyl)-3-(2-cyanoacetamido)butanoate
1441058-82-7

methyl 3-(4-butoxyphenyl)-3-(2-cyanoacetamido)butanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 5h;87%
methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine
910789-32-1

methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

C6H12BrN

C6H12BrN

3-((3R,4R)-4-methyl-3-(methyl(7-p-toluenesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-yl)-3-oxopropionitrile

3-((3R,4R)-4-methyl-3-(methyl(7-p-toluenesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-yl)-3-oxopropionitrile

Conditions
ConditionsYield
Stage #1: methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine; C6H12BrN With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium tert-butylate; lead(II) chloride In 1,4-dioxane at 20℃; for 5h; Inert atmosphere;
Stage #2: cyanoacetic acid chloride With pyridine at 20 - 30℃; for 10h; Reagent/catalyst; Solvent;		87%
...Expand
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

1-(3-amino-7-methoxy-benzofuran-2-yl)-ethanone
916329-09-4

1-(3-amino-7-methoxy-benzofuran-2-yl)-ethanone

N-(2-acetyl-7-methoxy-benzofuran-3-yl)-2-cyano-acetamide

N-(2-acetyl-7-methoxy-benzofuran-3-yl)-2-cyano-acetamide

Conditions
ConditionsYield
In tetrahydrofuran at 68℃; for 6h;86%
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
350255-13-9

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

Cyano-acetic acid (3aR,5R,6S,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
132640-91-6

Cyano-acetic acid (3aR,5R,6S,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Conditions
ConditionsYield
With silver cyanide In toluene at 80℃; for 4h;85%
cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

ethyl 2-(3-(4-methoxyphenylamino)-3-oxopropanamido)-2-methyl-4-oxo-4-p-tolylbutanoate
1441058-46-3

ethyl 2-(3-(4-methoxyphenylamino)-3-oxopropanamido)-2-methyl-4-oxo-4-p-tolylbutanoate

ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate
1441058-88-3

ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 1h; Inert atmosphere;84%
1,3-dibromo-2-hydroxypropane
96-21-9

1,3-dibromo-2-hydroxypropane

cyanoacetic acid chloride
16130-58-8

cyanoacetic acid chloride

2-bromo-1-(bromomethyl)ethyl cyanoacetate

2-bromo-1-(bromomethyl)ethyl cyanoacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;83%

CYANOACETYL CHLORIDE Chemical Properties

Product Name: Cyanoacetyl chloride (CAS NO.16130-58-8)


Molecular Formula: C3H2ClNO
Molecular Weight: 103.51g/mol
Mol File: 16130-58-8.mol
Appearance: Colorless transparent liquid
Boiling point: 180.9 °C at 760 mmHg
Flash Point: 63.2 °C
Density: 1.294 g/cm3
Solubility: Soluble in ether
Surface Tension: 41.8 dyne/cm
Enthalpy of Vaporization: 41.71 kJ/mol
Vapour Pressure: 0.876 mmHg at 25°C
XLogP3-AA: 0.7
H-Bond Donor: 0
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Topological Polar Surface Area: 40.9
Heavy Atom Count: 6
Complexity: 101
Covalently-Bonded Unit Count: 1

CYANOACETYL CHLORIDE Uses

 Cyanoacetyl chloride (CAS NO.16130-58-8) is a cephalosporin acetonitrile (Cefacetrile) an important intermediate.

CYANOACETYL CHLORIDE Consensus Reports

Cyanide compounds are on the Community Right-To-Know List.

CYANOACETYL CHLORIDE Safety Profile

A poison. A storage hazard. It may explode at room temperature. Upon decomposition it emits toxic fumes of Cl−, NOx, and CN−. See also CYANIDE and CHLORIDES.

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