Product Name

  • Name

    3-Chlorobenzonitrile

  • EINECS 212-172-6
  • CAS No. 766-84-7
  • Article Data150
  • CAS DataBase
  • Density 1.23 g/cm3
  • Solubility Insoluble in water
  • Melting Point 38-42 °C
  • Formula C7H4ClN
  • Boiling Point 203.4 °C at 760 mmHg
  • Molecular Weight 137.568
  • Flash Point 97.2
  • Transport Information
  • Appearance slightly beige to light pink crystalline powder
  • Safety 23-24/25
  • Risk Codes 36-21/22
  • Molecular Structure Molecular Structure of 766-84-7 (3-Chlorobenzonitrile)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Benzonitrile,m-chloro- (7CI,8CI);NSC 59733;m-Chlorobenzonitrile;m-Chlorocyanobenzene;
  • PSA 23.79000
  • LogP 2.21168

Synthetic route

(3‐cyanophenyl)boronic acid
150255-96-2

(3‐cyanophenyl)boronic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With N-chloro-succinimide; copper(l) chloride In acetonitrile at 80℃; for 1h;98%
With N-chloro-succinimide In acetonitrile at 80℃; for 12h;97%
C14H10ClNO2

C14H10ClNO2

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane; toluene at 20℃; for 0.0833333h;97%
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.0833333h; Schlenk technique;85%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With copper(II) oxide; hydroxylamine hydrochloride In neat (no solvent) for 0.0263889h; Mechanism; Reagent/catalyst; Microwave irradiation; Green chemistry;95%
With ammonium acetate; phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 64h;94%
Stage #1: m-Chlorobenzaldehyde With ammonia In water at 20℃; for 0.166667h;
Stage #2: With tetra-N-butylammonium tribromide In water at 20℃; for 3h;		93%
m-chlorobenzylamine
4152-90-3

m-chlorobenzylamine

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 15h; Reagent/catalyst;95%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;90%
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In dichloromethane at 20℃; for 10h; Oxidation;87%
3-chlorobenzaldehyde oxime
34158-71-9

3-chlorobenzaldehyde oxime

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With acetonitrile for 1.5h; Reflux; Green chemistry;95%
Stage #1: 3-chlorobenzaldehyde oxime With Bromotrichloromethane; triphenylphosphine In dichloromethane for 0.416667h; Reflux;
Stage #2: With triethylamine In dichloromethane for 8h; Reflux;		81%
With 1,2-bis(3-fluorophenyl)diselane; dihydrogen peroxide In acetonitrile at 65℃; for 24h;80%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

potassium ferrocyanide

potassium ferrocyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;94%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 13h;88%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;
With sodium carbonate In N,N-dimethyl-formamide at 120℃;
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium ferrocyanide

potassium ferrocyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.05h; Microwave irradiation; chemoselective reaction;93%
With tri-tert-butyl phosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 17h; Inert atmosphere;69 %Chromat.
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;
With sodium carbonate In N,N-dimethyl-formamide at 120℃;
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium cyanide
151-50-8

potassium cyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; tributyltin chloride; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;92%
potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With CHF3O3S*C52H45NO2P2Pd; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3.25h; chemoselective reaction;92%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 6h;91%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-bromo-benzenesulfonic acid-(4-chloro-anilide)
6295-97-2

4-bromo-benzenesulfonic acid-(4-chloro-anilide)

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux;A 91%
B n/a
...Expand
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-nitro-N-(4-chlorophenyl)benzenesulfonamide
16937-03-4

4-nitro-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 13h; Catalytic behavior; Reflux;A 91%
B n/a
...Expand
3-chlorobenzamide
618-48-4

3-chlorobenzamide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With C8H14N2O4S In dichloromethane for 1h; Reflux;90%
With vanadium oxide on hydrotalcite (V/HT) In 1,3,5-trimethyl-benzene for 24h; Reflux;89%
Stage #1: 3-chlorobenzamide With C39H45N2 In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;		82%
m-chlorobenzyl alcohol
873-63-2

m-chlorobenzyl alcohol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With ammonium acetate; iodine at 100℃; for 3h;90%
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 20℃; for 24h;85%
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;82%
With copper(II) choride dihydrate; ammonium formate; potassium carbonate In neat (no solvent) at 135℃; under 760.051 Torr; for 24h; Sealed tube; Schlenk technique; Green chemistry;75%
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Microwave irradiation; chemoselective reaction;90%
With C20H28Br2N2O4Pd2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.333333h; Inert atmosphere; Microwave irradiation; chemoselective reaction;58%
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium hexacyanoferrate(II) hydrate

potassium hexacyanoferrate(II) hydrate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;90%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide
119986-58-2

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-methyl-N-(4-chlorophenyl)benzenesulfonamide
2903-34-6

4-methyl-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 16h; Catalytic behavior; Reflux;A 90%
B n/a
...Expand
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

2-(dimethylamino)malononitrile
19555-13-6

2-(dimethylamino)malononitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With copper(II) orthophosphate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Sealed tube;89%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

3-chlorobenzaldehyde oxime
34158-71-9

3-chlorobenzaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; FeOO280 In toluene for 7h; Condensation; dehydration; Heating;A 86%
B 14%
3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

A

3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

B

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With Bromotrichloromethane; trichloroisocyanuric acid; bromine at 10 - 120℃; for 0.5h; Photolysis;A 84%
B 10%
m-chlorobenzylamine
4152-90-3

m-chlorobenzylamine

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

N-(3-chlorobenzylidene)-1-(3-chlorophenyl)methylamine
161723-68-8

N-(3-chlorobenzylidene)-1-(3-chlorophenyl)methylamine

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethylethylenediamine; copper(l) chloride In toluene at 80℃; for 24h; Sealed tube; Schlenk technique; chemoselective reaction;A 82%
B n/a
With iodine; tert-butylamine In acetonitrile for 6h; Ambient temperature;A 86 % Chromat.
B 9 % Chromat.
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C63H51N2O3P2Ru(1+)*ClO4(1-); oxygen In toluene at 90℃; under 760.051 Torr; for 20h;A 50 %Chromat.
B 20 %Chromat.
3-chlorophenylacetic acid
1878-65-5

3-chlorophenylacetic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 38h; Green chemistry;80%
3'-Chloroacetophenone
99-02-5

3'-Chloroacetophenone

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With oxygen; copper(l) cyanide In dimethyl sulfoxide at 150℃;78%
3-chlorobenzoate
535-80-8

3-chlorobenzoate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With aluminum oxide; aminosulfonic acid; urea for 0.0833333h; Irradiation;77%
With ammonium hydroxide; thionyl chloride 2.) dioxane, 3.) reflux; Multistep reaction;
N-cyano-N-phenyl-p-toluenesulfonamide
55305-43-6

N-cyano-N-phenyl-p-toluenesulfonamide

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With hydroxo(1,5-cyclooctadiene)rhodium (I) dimer; potassium carbonate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere;76%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

A

3-chlorobenzamide
618-48-4

3-chlorobenzamide

B

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Inert atmosphere; Sealed tube; Green chemistry;A 74%
B n/a
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

2,2-dimethylmalononitrile
7321-55-3

2,2-dimethylmalononitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
Stage #1: 1-bromo-3-chlorobenzene With TurboGrignard In tetrahydrofuran at 0℃; for 5h;
Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 23℃; for 1h;		73%
3-Carboxyphenol
99-06-9

3-Carboxyphenol

acetonitrile
75-05-8

acetonitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 150℃; for 6h; Autoclave;72%
(E)-3-chlorobenzaldehyde oxime
3717-33-7, 34158-71-9, 4006-79-5

(E)-3-chlorobenzaldehyde oxime

acetonitrile
75-05-8

acetonitrile

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

3-(3-chlorophenyl)-5-methyl-1,2,4-oxadiazole
95124-66-6

3-(3-chlorophenyl)-5-methyl-1,2,4-oxadiazole

C

3-chlorobenzoate
535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate at 70℃; for 1h;A n/a
B 70%
C 7%
...Expand
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-N-hydroxy-benzamidine
22179-77-7

3-chloro-N-hydroxy-benzamidine

Conditions
ConditionsYield
With hydroxylamine monohydrate In ethanol at 90℃; for 1h; Sealed tube;100%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 80℃; for 2h;85.9%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water at 25℃; for 70h;80%
ethanol
64-17-5

ethanol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethyl 3-chlorobenzimidate hydrochloride
60612-87-5

ethyl 3-chlorobenzimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0 - 20℃; for 16.33h;100%
With hydrogenchloride at 0 - 20℃; for 16.3333h;100%
With hydrogenchloride at 0 - 20℃; for 16.3333h;100%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

5-(m-chlorophenyl)tetrazole
41421-28-7

5-(m-chlorophenyl)tetrazole

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;		99%
With sodium azide at 120℃; for 0.0833333h;98%
With sodium azide at 130℃; for 6.75h; Catalytic behavior;98%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorobenzamide
618-48-4

3-chlorobenzamide

Conditions
ConditionsYield
With water; potassium carbonate at 150℃; for 0.25h; Microwave irradiation;99%
With C12H24O16Ru3*2H2O In water at 110℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere; Autoclave;99%
With polystyrene-triethylenetetramine anchored ruthenium(II) complex; air In water at 90℃; for 7h; Green chemistry;95%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-benzylamine; hydrochloride
42365-42-4

3-chloro-benzylamine; hydrochloride

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile With [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; diethylphenylsilane at 20℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;		99%
Stage #1: 3-chloro-benzonitrile With MnBr(CO)2[NH(CH2CH2P(iPr)2)2]; hydrogen; sodium t-butanolate In toluene at 120℃; under 37503.8 Torr; for 24h; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether		96%
Stage #1: 3-chloro-benzonitrile With cobalt pivalate; 1,1,3,3-Tetramethyldisiloxane; tert-butylisonitrile at 80℃; for 24h;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.5h;		95%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

phenylboronic acid
98-80-6

phenylboronic acid

3-phenylbenzonitrile
24973-50-0

3-phenylbenzonitrile

Conditions
ConditionsYield
With C16H36N(1+)*C32H25Cl2Fe2N2O3PdS(1-); potassium carbonate In water for 0.25h; Suzuki coupling; Microwave irradiation;99%
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 1h; Suzuki-Miyaura coupling; Heating;98%
With potassium phosphate; 2-(diphenylphosphino)phenylferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 90℃; for 24h; Suzuki-Miyaura coupling;96%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

n-pentylmagnesium bromide
693-25-4

n-pentylmagnesium bromide

1-(3-chlorophenyl)hexan-1-one

1-(3-chlorophenyl)hexan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; n-pentylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 20℃;		99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

pentafluorophenyl potassium carboxylate
58521-27-0

pentafluorophenyl potassium carboxylate

2′,3′,4′,5′,6′-pentafluorobiphenyl-3-carbonitrile

2′,3′,4′,5′,6′-pentafluorobiphenyl-3-carbonitrile

Conditions
ConditionsYield
With palladium diacetate; tricyclohexylphosphine In diethylene glycol dimethyl ether at 130℃; for 24h; Inert atmosphere; Sealed tube;99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

pentylmagnesium chloride
6393-56-2

pentylmagnesium chloride

1-(3-chlorophenyl)hexan-1-one

1-(3-chlorophenyl)hexan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; pentylmagnesium chloride In tetrahydrofuran; diethyl ether at 20℃; for 144h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0℃;		99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

cyclopentylzinc bromide lithium chloride

cyclopentylzinc bromide lithium chloride

3-cyclopentylbenzonitrile

3-cyclopentylbenzonitrile

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 20℃; for 0.5h; Negishi Coupling; Schlenk technique; Inert atmosphere;99%
styrene
292638-84-7

styrene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

(E)-3-styrylbenzonitrile
14064-35-8

(E)-3-styrylbenzonitrile

Conditions
ConditionsYield
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 16h; Heck Reaction;99%
With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 2h; Heck Reaction; Inert atmosphere; Schlenk technique;99%
4,5,6,7-Tetrahydrocyclohexa-1,2,3-selenadiazol
35676-30-3

4,5,6,7-Tetrahydrocyclohexa-1,2,3-selenadiazol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-(3-chlorophenyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole

3-(3-chlorophenyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;99%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;99%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;99%
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

benzaldehyde
100-52-7

benzaldehyde

N-benzyl-1-(3-chlorophenyl)methanaminium chloride

N-benzyl-1-(3-chlorophenyl)methanaminium chloride

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; benzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether		99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethylenediamine
107-15-3

ethylenediamine

2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole
27429-86-3

2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With tetraphosphorus decasulfide for 0.0416667h; microwave irradiation;98%
With toluene-4-sulfonic acid for 0.416667h; Reflux; neat (no solvent);92%
With sulfur at 20℃; for 0.116667h; ultrasonic irradiation;89%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

2-(3-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine
91552-24-8

2-(3-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine

Conditions
ConditionsYield
With Montmorillonite K-10 for 7h; Microwave irradiation;98%
With montmorillonite KSF at 30℃; for 0.166667h; Sonication;98%
With phosphotungstic acid for 0.121667h; Microwave irradiation; chemoselective reaction;90%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

di(p-tolyl)borinic acid
66117-64-4

di(p-tolyl)borinic acid

4'-methyl-[1,1'-biphenyl]-3-carbonitrile
133909-96-3

4'-methyl-[1,1'-biphenyl]-3-carbonitrile

Conditions
ConditionsYield
With NiCl2(Tris-(4-methoxy-phenyl)-phosphin)2; potassium phosphate tribasic trihydrate; P(p-CH3OC6H4)3 In toluene at 110℃; for 5h; Inert atmosphere;98%
With bis(triphenylphosphine)nickel(II) chloride; potassium phosphate tribasic trihydrate; 1-n-butyl-3-methylimidazolim bromide In toluene at 110℃; for 6h; Inert atmosphere;93%
ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate
60474-27-3

ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethyl 3-(3-chlorophenyl)-5-phenylisothiazole-4-carboxylate

ethyl 3-(3-chlorophenyl)-5-phenylisothiazole-4-carboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In chlorobenzene at 130℃; for 1h; Glovebox;98%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorobenzoate
535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With benzene-1,2-dicarboxylic acid for 0.666667h; microwave-irradiation;97%
With potassium hydroxide In ethylene glycol at 170℃; for 7h;
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2'-methyl-[1,1'-biphenyl]-3-carbonitrile
253678-80-7

2'-methyl-[1,1'-biphenyl]-3-carbonitrile

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole In 1,4-dioxane at 90℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;97%
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; potassium phosphate; palladium diacetate In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura coupling;94%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;81%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

1-propylmagnesium chloride
2234-82-4

1-propylmagnesium chloride

1-(3-chlorophenyl)butan-1-one
21550-08-3

1-(3-chlorophenyl)butan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride; copper(l) chloride In tetrahydrofuran; diethyl ether for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 20℃;
Stage #3: With water; hydrogenchloride at 90℃; for 1h;		97%
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 20℃;		88%
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 96h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 20℃; for 1h;		88%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

cyclohexylmagnesiumchloride
931-51-1

cyclohexylmagnesiumchloride

(3-chlorophenyl)(cyclohexyl)methanone
211985-77-2

(3-chlorophenyl)(cyclohexyl)methanone

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; cyclohexylmagnesiumchloride; copper(l) chloride In tetrahydrofuran; diethyl ether for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 20℃;
Stage #3: With water; hydrogenchloride at 90℃; for 1h;		97%
carbon monoxide
201230-82-2

carbon monoxide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

Conditions
ConditionsYield
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; water; palladium diacetate; potassium carbonate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 15h;97%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

m-cyanophenol
873-62-1

m-cyanophenol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;97%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;91%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;90%
1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

C14H24ClNO2Si3

C14H24ClNO2Si3

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;97%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-N-hydroxybenzimidamide
22179-77-7

3-chloro-N-hydroxybenzimidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 6h; Reflux;96%
With hydroxylamine hydrochloride; potassium carbonate In ethanol
With hydroxylamine hydrochloride; sodium carbonate In ethanol Heating;
dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole
109345-74-6

4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole

Conditions
ConditionsYield
dirhodium tetraacetate In chloroform for 8h; Heating;96%
dirhodium tetraacetate In chloroform Heating;96%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorothiobenzamide
2548-79-0

3-chlorothiobenzamide

Conditions
ConditionsYield
With sodium monohydrogen sulfide x-hydrate; magnesium(II) chloride hexahydrate In N,N-dimethyl-formamide at 20℃; for 2h;96%
With diammonium sulfide; 1,6-bis(3-methylimidazolium-1-yl)hexane dichloride at 70℃; for 0.05h;94%
With diphosphorus pentasulfide; ethanol for 4h; Heating;88%

3-Chlorobenzonitrile Specification

The 3-Chlorobenzonitrile with CAS registry number of 766-84-7 is also known as Benzonitrile, m-chloro-. The IUPAC name and product name are the same. It belongs to product categories of Boron, Nitrile, Thio,& TM-Cpds; Halides; Aromatic Nitriles; Chlorine Compounds; Nitriles; C6 to C7; Cyanides/Nitriles; Nitrogen Compounds. Its EINECS registry number is 212-172-6. In addition, the formula is C7H4ClN and the molecular weight is 137.57. This chemical is a white crystal and should be sealed in a ventilated and dry place.

Physical properties about 3-Chlorobenzonitrile are: (1)ACD/LogP: 2.35; (2)ACD/LogD (pH 5.5): 2.35; (3)ACD/LogD (pH 7.4): 2.35; (4)ACD/BCF (pH 5.5): 35.98; (5)ACD/BCF (pH 7.4): 35.98; (6)ACD/KOC (pH 5.5): 452.29; (7)ACD/KOC (pH 7.4): 452.29; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.563; (10)Molar Refractivity: 36.14 cm3; (11)Molar Volume: 111.2 cm3; (12)Surface Tension: 46.2 dyne/cm; (13)Density: 1.23 g/cm3; (14)Flash Point: 97.2 °C; (15)Enthalpy of Vaporization: 43.97 kJ/mol; (16)Boiling Point: 203.4 °C at 760 mmHg; (17)Vapour Pressure: 0.278 mmHg at 25 °C.

Preparation of 3-Chlorobenzonitrile: it is prepared by reaction of 3-chloro-benzamide. The reaction needs reagent 2-(trifluoroacetyloxy)pyridine and  solventacetonitrile and other condition of heating for 5 hours. The yield is about 77%.

3-Chlorobenzonitrile is prepared by reaction of 3-chloro-benzamide.

Uses of 3-Chlorobenzonitrile: it is used as intermediate of medicine, pesticide and dye. It is used to produce 1-(m-chlorophenyl)pentan-1-one by reaction with butyllithium. The reaction occurs with reagent hexane and diethyl ether at ambient temperature. The yield is about 67%.

3-Chlorobenzonitrile is used to produce 1-(m-chlorophenyl)pentan-1-one by reaction with butyllithium.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes and harmful in contact with skin and if swallowed. During using it, do not breathe gas/fumes/vapour/spray and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=CC(=C1)Cl)C#N
2. InChI: InChI=1S/C7H4ClN/c8-7-3-1-2-6(4-7)5-9/h1-4H
3. InChIKey: WBUOVKBZJOIOAE-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 800mg/kg (800mg/kg)   Farmaco, Edizione Scientifica. Vol. 41, Pg. 41, 1986.

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