Product Name

  • Name

    4-Chlorobutyronitrile

  • EINECS 211-031-6
  • CAS No. 628-20-6
  • Article Data29
  • CAS DataBase
  • Density 1.042 g/cm3
  • Solubility Immiscible with water
  • Melting Point -44oC
  • Formula C4H6ClN
  • Boiling Point 191 °C at 760 mmHg
  • Molecular Weight 103.551
  • Flash Point 85 °C
  • Transport Information UN 3276
  • Appearance Colorless transparent liquid
  • Safety 45-7-36/37/39
  • Risk Codes 25-36/37/38
  • Molecular Structure Molecular Structure of 628-20-6 (4-Chlorobutyronitrile)
  • Hazard Symbols ToxicT,IrritantXi
  • Synonyms Butyronitrile,4-chloro- (6CI,7CI,8CI);4-Chlorobutanenitrile;NSC8410;g-Chlorobutyronitrile;4-Chlorobutyronitrile;
  • PSA 23.79000
  • LogP 1.52898

Synthetic route

1-chloro-4,4-dihydroxy-4-butylamine

1-chloro-4,4-dihydroxy-4-butylamine

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With aluminum oxide; calcium hydroxide; 2-hydroxynitrobenzene In cyclohexane at 77 - 97℃; for 5.5h; Temperature; Reflux;92%
4-chlorobutyramide
2455-04-1

4-chlorobutyramide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With formaldehyd; formic acid; acetonitrile for 12h; Heating;87%
2-((cyclobutylideneamino)oxy)-2-methylpropanoic acid

2-((cyclobutylideneamino)oxy)-2-methylpropanoic acid

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With N-chloro-succinimide; potassium acetate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 1h; Irradiation; Sealed tube; Inert atmosphere;59%
5-chloro-valeric acid
1119-46-6

5-chloro-valeric acid

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage;57%
propyl cyanide
109-74-0

propyl cyanide

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With chlorine Irradiation.mit UV-Licht;
With sodium persulfate; copper dichloride In water at 85 - 90℃; for 10h; Yield given. Yields of byproduct given;
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity;
hydroxymethyl propionamide
927-60-6

hydroxymethyl propionamide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With thionyl chloride; benzene
With trichlorophosphate; benzene
With phosphorus trichloride
ethanol
64-17-5

ethanol

sodium cyanide
143-33-9

sodium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

ethanol
64-17-5

ethanol

potassium cyanide
151-50-8

potassium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

Glutaronitrile
544-13-8

Glutaronitrile

sodium cyanide
143-33-9

sodium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

Glutaronitrile
544-13-8

Glutaronitrile

Conditions
ConditionsYield
With methanol
potassium cyanide
151-50-8

potassium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With ethanol
With ethanol; water Alkohol abdestillieren,Wasser zum Rueckstand geben,abgeschiedene Oelschicht abheben und fraktionieren;
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

4-butanolide
96-48-0

4-butanolide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
(i) liq. NH3, (ii) SOCl2; Multistep reaction;
tetraethylammoniumcyanide
13435-20-6

tetraethylammoniumcyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
In dichloromethane
2,4-dichlorobutanenitrile
77100-86-8

2,4-dichlorobutanenitrile

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With acetic acid; zinc for 2h; Yield given;
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

alcoholic KCN

alcoholic KCN

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

propyl cyanide
109-74-0

propyl cyanide

chlorine
7782-50-5

chlorine

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
mit UV-Licht in der Dampfphase.Irradiation;
propyl cyanide
109-74-0

propyl cyanide

chlorine
7782-50-5

chlorine

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

C

2-chlorobutyronitrile
4158-37-6

2-chlorobutyronitrile

Conditions
ConditionsYield
at 450℃; Dampfphase;
propyl cyanide
109-74-0

propyl cyanide

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

2-chloro-butyronitrile and 3-chloro-butyronitrile

2-chloro-butyronitrile and 3-chloro-butyronitrile

Conditions
ConditionsYield
With chlorine at 450℃;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

4-(methylthio)butyronitrile
59121-24-3

4-(methylthio)butyronitrile

Conditions
ConditionsYield
In ethanol at 20℃; for 25h; Inert atmosphere; Cooling with ice;100%
In ethanol
In ethanol at 25℃; for 15h;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

tert-butyl N-(benzyloxy)carbamate
79722-21-7

tert-butyl N-(benzyloxy)carbamate

4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile
489452-95-1

4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile

Conditions
ConditionsYield
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 80℃; for 6h;
100%
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere;
98%
With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 60 - 70℃; for 5h;80%
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0℃; Inert atmosphere;
Stage #2: 4-Chlorobutyronitrile In N,N-dimethyl-formamide at 85℃; Inert atmosphere;
70%
With sodium hydride; potassium iodide In N,N-dimethyl-formamide
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

(S)-(-)-[1-phenylethyl]-1H-imidazole
129696-60-2

(S)-(-)-[1-phenylethyl]-1H-imidazole

3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride
1253119-37-7

3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In acetonitrile Reflux;100%
morpholine
110-91-8

morpholine

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

3-(morpholin-4-yl)-butanenitrile
5807-11-4

3-(morpholin-4-yl)-butanenitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 72h;99%
In toluene for 7h; Reflux;65%
at 20℃;63%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium chloride In water; dimethyl sulfoxide98%
With sodium hydride In ethylene glycol; mineral oil at 20 - 80℃; for 0.5h; Solvent; Reagent/catalyst;97.2%
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h;89%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

methyl N-tosylanthranilate
50998-74-8

methyl N-tosylanthranilate

methyl 2-{(3-cyanopropyl)[(4-methylphenyl)sulfonyl]amino}benzoate
105895-93-0

methyl 2-{(3-cyanopropyl)[(4-methylphenyl)sulfonyl]amino}benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In butanone for 12h; Heating;98%
With potassium carbonate; potassium iodide In acetone for 168h; Heating;95%
With potassium carbonate; potassium iodide In butanone for 12h; Reflux;80.1%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

[1(R)-methyl-3-[(phenylmethyl)amino]propyl]carbamic acid, 1,1-dimethylethyl ester
170367-70-1

[1(R)-methyl-3-[(phenylmethyl)amino]propyl]carbamic acid, 1,1-dimethylethyl ester

3-[(3-cyanopropyl)(phenylmethyl)amino-1(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester
170367-71-2

3-[(3-cyanopropyl)(phenylmethyl)amino-1(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In butan-1-ol for 20h; Alkylation; Heating;98%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

N-(2,4,6-trimethylphenyl)imidazole
25364-44-7

N-(2,4,6-trimethylphenyl)imidazole

1-(2,4,6-trimethylphenyl)-3-(butylnitrile)imidazolium chloride
1247011-82-0

1-(2,4,6-trimethylphenyl)-3-(butylnitrile)imidazolium chloride

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 72h; Reflux; Inert atmosphere;98%
In 1,2-dimethoxyethane Inert atmosphere; Heating;98%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

2-bromo-4-chlorobutyronitrile

2-bromo-4-chlorobutyronitrile

Conditions
ConditionsYield
With triphenyl phosphite; bromine at 80℃; for 4h; Reagent/catalyst;98%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

(3-cyanopropyl)dimethylsilyl chloride
18156-15-5

(3-cyanopropyl)dimethylsilyl chloride

Conditions
ConditionsYield
With magnesium; ethylene dibromide; manganese(ll) chloride In tetrahydrofuran at 65℃; for 2h; Inert atmosphere;96.1%
Stage #1: 4-Chlorobutyronitrile With sodium In toluene at 108 - 110℃; for 3h;
Stage #2: dimethylsilicon dichloride In toluene at 40 - 45℃; for 4h; Temperature;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

1-(2-Methoxyphenyl)piperazine
35386-24-4

1-(2-Methoxyphenyl)piperazine

4‐[4‐(2‐methoxyphenyl)piperazin‐1‐yl]butannitrile
25024-99-1

4‐[4‐(2‐methoxyphenyl)piperazin‐1‐yl]butannitrile

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 60℃; for 1.33333h; Microwave irradiation; Neat (no solvent); chemoselective reaction;96%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester
29247-79-8

N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester

methyl 4-chloro-2-(N-tosyl-3-cyanopropylamino)benzoate
105896-01-3

methyl 4-chloro-2-(N-tosyl-3-cyanopropylamino)benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 168h; Heating;95%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

N-[N-(tert-Butyloxycarbonyl)-3-aminopropyl]benzylamine
90914-08-2

N-[N-(tert-Butyloxycarbonyl)-3-aminopropyl]benzylamine

N-[N-(tert-Butoxycarbonyl)-3-aminopropyl]-N-(3-cyanopropyl)benzylamine
90914-11-7

N-[N-(tert-Butoxycarbonyl)-3-aminopropyl]-N-(3-cyanopropyl)benzylamine

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In butan-1-ol for 48h; Heating;95%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

thiophenol
108-98-5

thiophenol

4-(phenylthio)butanenitrile
35756-39-9

4-(phenylthio)butanenitrile

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 48h; Inert atmosphere;95%
With triethylamine In N,N-dimethyl-formamide at 25℃;
With sodium methylate; sodium iodide 1.) methanol, 1 h, 2.) reflux, 12 h; Yield given. Multistep reaction;
salicylonitrile
611-20-1

salicylonitrile

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

4-(2-cyanophenoxy)butanenitrile

4-(2-cyanophenoxy)butanenitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Heating;95%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

1,2,3,4-tetrahydro-4-methylspiro
127934-39-8

1,2,3,4-tetrahydro-4-methylspiro

N-(γ-cyanopropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]
522592-78-5

N-(γ-cyanopropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In butan-1-ol Heating;95%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

1-(3'-cyanopropyl)-3-methylimidazolium chloride

1-(3'-cyanopropyl)-3-methylimidazolium chloride

Conditions
ConditionsYield
at 80℃; for 24h;95%
at 70℃; for 48h; Neat (no solvent); Sealed vial;92%
at 80℃; for 24h;82%
Heating;78%
at 79.84℃; for 48h;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

trans-hydridochloro-di-{1,2-bis(diphenylphosphino)ethane}iron(II)
19392-93-9, 32490-70-3

trans-hydridochloro-di-{1,2-bis(diphenylphosphino)ethane}iron(II)

trans-[FeH(4-chlorobutyronitrile)(dppe)2]Cl
252659-30-6

trans-[FeH(4-chlorobutyronitrile)(dppe)2]Cl

Conditions
ConditionsYield
In further solvent(s) Ar-atmosphere; stirring in ClCH2CH2CH2CN for 1 h; filtration, solvent removal (vac.), washing (Et2O); elem. anal.;95%
methanol
67-56-1

methanol

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

methyl 3-chloropropanimidate hydrochloride
77570-15-1

methyl 3-chloropropanimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 20℃; for 4h;94%
With hydrogenchloride In diethyl ether at -20℃; for 24h;90%
With hydrogenchloride In diethyl ether at 0℃; for 24h;70%
With hydrogenchloride In diethyl ether at -20 - 0℃; for 28h;
1-chloro-4,4-dihydroxy-4-butylamine

1-chloro-4,4-dihydroxy-4-butylamine

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With aluminum oxide; calcium hydroxide; 2-hydroxynitrobenzene In cyclohexane at 77 - 97℃; for 5.5h; Temperature; Reflux;92%
4-chlorobutyramide
2455-04-1

4-chlorobutyramide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With formaldehyd; formic acid; acetonitrile for 12h; Heating;87%
2-((cyclobutylideneamino)oxy)-2-methylpropanoic acid

2-((cyclobutylideneamino)oxy)-2-methylpropanoic acid

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With N-chloro-succinimide; potassium acetate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 1h; Irradiation; Sealed tube; Inert atmosphere;59%
5-chloro-valeric acid
1119-46-6

5-chloro-valeric acid

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage;57%
propyl cyanide
109-74-0

propyl cyanide

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With chlorine Irradiation.mit UV-Licht;
With sodium persulfate; copper dichloride In water at 85 - 90℃; for 10h; Yield given. Yields of byproduct given;
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity;
hydroxymethyl propionamide
927-60-6

hydroxymethyl propionamide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With thionyl chloride; benzene
With trichlorophosphate; benzene
With phosphorus trichloride
ethanol
64-17-5

ethanol

sodium cyanide
143-33-9

sodium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

ethanol
64-17-5

ethanol

potassium cyanide
151-50-8

potassium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

Glutaronitrile
544-13-8

Glutaronitrile

sodium cyanide
143-33-9

sodium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

Glutaronitrile
544-13-8

Glutaronitrile

Conditions
ConditionsYield
With methanol
potassium cyanide
151-50-8

potassium cyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With ethanol
With ethanol; water Alkohol abdestillieren,Wasser zum Rueckstand geben,abgeschiedene Oelschicht abheben und fraktionieren;
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

4-butanolide
96-48-0

4-butanolide

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
(i) liq. NH3, (ii) SOCl2; Multistep reaction;
tetraethylammoniumcyanide
13435-20-6

tetraethylammoniumcyanide

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
In dichloromethane
2,4-dichlorobutanenitrile
77100-86-8

2,4-dichlorobutanenitrile

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
With acetic acid; zinc for 2h; Yield given;
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

alcoholic KCN

alcoholic KCN

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

propyl cyanide
109-74-0

propyl cyanide

chlorine
7782-50-5

chlorine

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

Conditions
ConditionsYield
mit UV-Licht in der Dampfphase.Irradiation;
propyl cyanide
109-74-0

propyl cyanide

chlorine
7782-50-5

chlorine

A

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

B

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

C

2-chlorobutyronitrile
4158-37-6

2-chlorobutyronitrile

Conditions
ConditionsYield
at 450℃; Dampfphase;
propyl cyanide
109-74-0

propyl cyanide

A

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

B

2-chloro-butyronitrile and 3-chloro-butyronitrile

2-chloro-butyronitrile and 3-chloro-butyronitrile

Conditions
ConditionsYield
With chlorine at 450℃;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

4-(methylthio)butyronitrile
59121-24-3

4-(methylthio)butyronitrile

Conditions
ConditionsYield
In ethanol at 20℃; for 25h; Inert atmosphere; Cooling with ice;100%
In ethanol
In ethanol at 25℃; for 15h;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

tert-butyl N-(benzyloxy)carbamate
79722-21-7

tert-butyl N-(benzyloxy)carbamate

4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile
489452-95-1

4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile

Conditions
ConditionsYield
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 80℃; for 6h;
100%
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere;
98%
With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 60 - 70℃; for 5h;80%
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0℃; Inert atmosphere;
Stage #2: 4-Chlorobutyronitrile In N,N-dimethyl-formamide at 85℃; Inert atmosphere;
70%
With sodium hydride; potassium iodide In N,N-dimethyl-formamide
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

(S)-(-)-[1-phenylethyl]-1H-imidazole
129696-60-2

(S)-(-)-[1-phenylethyl]-1H-imidazole

3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride
1253119-37-7

3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In acetonitrile Reflux;100%
morpholine
110-91-8

morpholine

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

3-(morpholin-4-yl)-butanenitrile
5807-11-4

3-(morpholin-4-yl)-butanenitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 72h;99%
In toluene for 7h; Reflux;65%
at 20℃;63%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium chloride In water; dimethyl sulfoxide98%
With sodium hydride In ethylene glycol; mineral oil at 20 - 80℃; for 0.5h; Solvent; Reagent/catalyst;97.2%
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h;89%

4-Chlorobutyronitrile Consensus Reports

Reported in EPA TSCA Inventory.

4-Chlorobutyronitrile Specification

1.Introduction of 4-Chlorobutyronitrile

The 4-Chlorobutanenitrile, with the CAS registry number 628-20-6, is also known as 1-Chloro-3-cyanopropane. It belongs to the product categories of Halogen compounds; Miscellaneous; Aliphatics; C1 to C5; Cyanides/Nitriles; Nitrogen Compounds. It should be stored in shady and cool warehouse and mainly used as Intermediate for Buflomedil.

2.Physical properties of 4-Chlorobutanenitrile

(1)ACD/LogP: 0.56; (2)ACD/LogD (pH 5.5): 0.56; (3)ACD/LogD (pH 7.4): 0.56; (4)ACD/BCF (pH 5.5): 1.57; (5)ACD/BCF (pH 7.4): 1.57; (6)ACD/KOC (pH 5.5): 48.04; (7)ACD/KOC (pH 7.4): 48.04; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.423; (11)Molar Refractivity: 25.34 cm3; (12)Molar Volume: 99.3 cm3; (13)Surface Tension: 32.9 dyne/cm; (14)Density: 1.042 g/cm3; (15)Flash Point: 85 °C; (16)Enthalpy of Vaporization: 42.72 kJ/mol; (17)Boiling Point: 191 °C at 760 mmHg; (18)Vapour Pressure: 0.525 mmHg at 25°C.

3.Structure descriptors of 4-Chlorobutyronitrile

(1)Canonical SMILES: C(CC#N)CCl
(2)InChI: InChI=1S/C4H6ClN/c5-3-1-2-4-6/h1-3H2
(3)InChIKey: ZFCFBWSVQWGOJJ-UHFFFAOYSA-N
 

4. Preparation of 4-Chlorobutyronitrile

The 4-Chlorobutyronitrile can be prepared by 1-chloro-3-bromopropane and potassium cyanide.

BrCH2CH2CH2Cl+KCN→ClCH2CH2CH2CN+KBr

5. Uses of 4-Chlorobutanenitrile

The 4-Chlorobutyronitrile can be used to produce 4-chloro-butyric acid at temperature of 240 °C. This reaction will need reagent CuSO4•H2O with reaction time of 1 hour. The yield is about 65%.

6.Safety information of 4-Chlorobutyronitrile

This chemical that at low levels can cause damage to health. It may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

7.The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 53380ug/kg (53.38mg/kg)   Archives of Toxicology. Vol. 55, Pg. 47, 1984.

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