766-84-7

Basic information

• Product Name: 3-Chlorobenzonitrile
• Synonyms: Benzonitrile, m-chloro-;m-chloro-benzonitril;m-Cyanochlorobenzene;3-CHLOROBENZONITRILE;M-CHLORO BENZONITRILE;MCBN;3-Chlorobenzonitrile m-Chlorobenzonitrile;3-CHLORBENZONITRIL 99%
• CAS NO: 766-84-7
• Molecular Formula: C₇H₄ClN
• Molecular Weight: 137.57
• EINECS: 212-172-6
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Halides;Aromatic Nitriles;Chlorine Compounds;Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 766-84-7.mol
• Article Data: 130

Chemical Properties

• Melting Point: 38-40 °C(lit.)
• Boiling Point: 94 °C (11 mmHg)
• Flash Point: 207 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.14
• Vapor Pressure: 0.278mmHg at 25°C
• Refractive Index: 1.4530 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: insoluble
• BRN: 1906694
• CAS DataBase Reference: 3-Chlorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorobenzonitrile(766-84-7)
• EPA Substance Registry System: 3-Chlorobenzonitrile(766-84-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36-21/22
• Safety Statements: 23-24/25
• RIDADR: 3439
• WGK Germany: 3
• RTECS: DI2600000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 766-84-7(Hazardous Substances Data)

Usage

Chemical Properties

SLIGHTLY BEIGE TO LIGHT PINK CRYSTALLINE POWDER

InChI:InChI=1/C7H4ClN/c8-7-3-1-2-6(4-7)5-9/h1-4H

Synthetic route

(3‐cyanophenyl)boronic acid (150255-96-2) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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 → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + potassium ferrocyanide → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + potassium ferrocyanide → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + potassium cyanide (151-50-8) → 3-chloro-benzonitrile (766-84-7)

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

potassium hexacyanoferrate(II) + 1-bromo-3-chlorobenzene (108-37-2) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With CHF3O3S*C52H45NO2P2Pd; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3.25h; chemoselective reaction;	92%

3-iodochlorobenzene (625-99-0) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 6h;	91%

3-chlorophenylboronic acid (63503-60-6) + 4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide → 3-chloro-benzonitrile (766-84-7) + 4-bromo-benzenesulfonic acid-(4-chloro-anilide) (6295-97-2)

Conditions	Yield
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

3-chlorophenylboronic acid (63503-60-6) + N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide → 3-chloro-benzonitrile (766-84-7) + 4-nitro-N-(4-chlorophenyl)benzenesulfonamide (16937-03-4)

Conditions	Yield
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

3-chlorobenzamide (618-48-4) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + potassiumhexacyanoferrate(II) trihydrate → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + potassium hexacyanoferrate(II) hydrate → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide (119986-58-2) → 3-chloro-benzonitrile (766-84-7) + 4-methyl-N-(4-chlorophenyl)benzenesulfonamide (2903-34-6)

Conditions	Yield
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

3-iodochlorobenzene (625-99-0) + 2-(dimethylamino)malononitrile (19555-13-6) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With copper(II) orthophosphate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Sealed tube;	89%

3-Chlorobenzaldehyde (587-04-2) → 3-chloro-benzonitrile (766-84-7) + 3-chlorobenzaldehyde oxime (34158-71-9)

Conditions	Yield
With hydroxylamine hydrochloride; FeOO280 In toluene for 7h; Condensation; dehydration; Heating;	A 86% B 14%

3-Cyanobenzoic acid (1877-72-1) → 3-cyanobromobenzene (6952-59-6) + 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With Bromotrichloromethane; trichloroisocyanuric acid; bromine at 10 - 120℃; for 0.5h; Photolysis;	A 84% B 10%

m-chlorobenzylamine (4152-90-3) → 3-chloro-benzonitrile (766-84-7) + N-(3-chlorobenzylidene)-1-(3-chlorophenyl)methylamine (161723-68-8)

Conditions	Yield
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-chloro-benzonitrile (766-84-7)

Conditions	Yield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 38h; Green chemistry;	80%

3'-Chloroacetophenone (99-02-5) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With oxygen; copper(l) cyanide In dimethyl sulfoxide at 150℃;	78%

3-chlorobenzoate (535-80-8) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + 3-chlorophenylboronic acid (63503-60-6) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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-chlorobenzamide (618-48-4) + 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + 2,2-dimethylmalononitrile (7321-55-3) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
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) + acetonitrile (75-05-8) → 3-chloro-benzonitrile (766-84-7)

Conditions	Yield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 150℃; for 6h; Autoclave;	72%

(E)-3-chlorobenzaldehyde oxime (3717-33-7, 34158-71-9, 4006-79-5) + acetonitrile (75-05-8) → 3-chloro-benzonitrile (766-84-7) + 3-(3-chlorophenyl)-5-methyl-1,2,4-oxadiazole (95124-66-6) + 3-chlorobenzoate (535-80-8)

Conditions	Yield
With ammonium cerium(IV) nitrate at 70℃; for 1h;	A n/a B 70% C 7%

3-chloro-benzonitrile (766-84-7) → 3-chloro-N-hydroxy-benzamidine (22179-77-7)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → ethyl 3-chlorobenzimidate hydrochloride (60612-87-5)

Conditions	Yield
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) → 5-(m-chlorophenyl)tetrazole (41421-28-7)

Conditions	Yield
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-chlorobenzamide (618-48-4)

Conditions	Yield
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-benzylamine; hydrochloride (42365-42-4)

Conditions	Yield
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) + phenylboronic acid (98-80-6) → 3-phenylbenzonitrile (24973-50-0)

Conditions	Yield
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) + n-pentylmagnesium bromide (693-25-4) → 1-(3-chlorophenyl)hexan-1-one

Conditions	Yield
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) + pentafluorophenyl potassium carboxylate (58521-27-0) → 2′,3′,4′,5′,6′-pentafluorobiphenyl-3-carbonitrile

Conditions	Yield
With palladium diacetate; tricyclohexylphosphine In diethylene glycol dimethyl ether at 130℃; for 24h; Inert atmosphere; Sealed tube;	99%

3-chloro-benzonitrile (766-84-7) + pentylmagnesium chloride (6393-56-2) → 1-(3-chlorophenyl)hexan-1-one

Conditions	Yield
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) + cyclopentylzinc bromide lithium chloride → 3-cyclopentylbenzonitrile

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → (E)-3-styrylbenzonitrile (14064-35-8)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → 3-(3-chlorophenyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole

Conditions	Yield
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-chloro-benzonitrile (766-84-7) → 3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions	Yield
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) + benzaldehyde (100-52-7) → N-benzyl-1-(3-chlorophenyl)methanaminium chloride

Conditions	Yield
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) + ethylenediamine (107-15-3) → 2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole (27429-86-3)

Conditions	Yield
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) + propan-1-ol-3-amine (156-87-6) → 2-(3-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine (91552-24-8)

Conditions	Yield
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) + di(p-tolyl)borinic acid (66117-64-4) → 4'-methyl-[1,1'-biphenyl]-3-carbonitrile (133909-96-3)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → ethyl 3-(3-chlorophenyl)-5-phenylisothiazole-4-carboxylate

Conditions	Yield
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-chlorobenzoate (535-80-8)

Conditions	Yield
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) + 2-Methylphenylboronic acid (16419-60-6) → 2'-methyl-[1,1'-biphenyl]-3-carbonitrile (253678-80-7)

Conditions	Yield
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) + 1-propylmagnesium chloride (2234-82-4) → 1-(3-chlorophenyl)butan-1-one (21550-08-3)

Conditions	Yield
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) + cyclohexylmagnesiumchloride (931-51-1) → (3-chlorophenyl)(cyclohexyl)methanone (211985-77-2)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → 3-Cyanobenzoic acid (1877-72-1)

Conditions	Yield
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) → m-cyanophenol (873-62-1)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → C14H24ClNO2Si3

Conditions	Yield
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-N-hydroxybenzimidamide (22179-77-7)

Conditions	Yield
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) + 3-chloro-benzonitrile (766-84-7) → 4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole (109345-74-6)

Conditions	Yield
dirhodium tetraacetate In chloroform for 8h; Heating;	96%
dirhodium tetraacetate In chloroform Heating;	96%

3-chloro-benzonitrile (766-84-7) → 3-chlorothiobenzamide (2548-79-0)

Conditions	Yield
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%

Upstream product

• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 860554-30-9 3-chlorobenzalchloroimine 
• 100-47-0 benzonitrile 
• 2237-30-1 m-cyanoaniline 
• 460-19-5 ethanedinitrile 
• 108-90-7 chlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 143-33-9 sodium cyanide 
• 108-37-2 1-bromo-3-chlorobenzene 
• 151-50-8 potassium cyanide 
• 3717-33-7 (E)-3-chlorobenzaldehyde oxime 
• 587-04-2 m-Chlorobenzaldehyde 
• 126799-85-7 3-chlorobenzylazide 

Downstream Products

• 54494-09-6 5-(3-chlorophenyl)-3-phenyl-1,2,4-oxadiazole 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 27545-73-9 3-amino-3-(3-chlorophenyl)acrylonitrile 
• 67567-61-7 2-(3-chloro-phenyl)-5-methoxy-oxazole 
• 63615-60-1 4-(3-chloro-phenyl)-2-morpholin-4-yl-quinazoline 
• 2905-65-9 methyl 3-chlorobenzoate 
• 125996-70-5 1-(3-chlorophenyl)-2-(4-pyridyl)ethanone 
• 56108-07-7 3-Chloro-benzimidic acid methyl ester; hydrochloride 
• 42916-71-2 1-(m-chlorophenyl)pentan-1-one 
• 76670-29-6 C₉H₉ClN₂O₂ 
• 124582-85-0 2-(3-Chloro-benzyl)-1,1,1,3,3,3-hexamethyl-disilazane 
• 109345-74-6 4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole 
• 73013-50-0 3-(2-oxopropyl)benzonitrile 
• 117995-34-3 C₁₄H₈N₂Te 

Relevant articles and documents

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