2042-37-7

Basic information

• Product Name: 2-Bromobenzonitrile
• Synonyms: 2-bromo-benzonitril;Benzonitrile, o-bromo-;o-bromo-benzonitril;BROMOBENZONITRILE(2-);1-BROMO-2-CYANOBENZENE;2-BROMOBENZONITRILE;O-BROMOBENZONITRILE;OBBN
• CAS NO: 2042-37-7
• Molecular Formula: C₇H₄BrN
• Molecular Weight: 182.02
• EINECS: 218-045-1
• Product Categories: blocks;Bromides;Carboxes;Boron, Nitrile, Thio,& TM-Cpds;Halides;Aromatic Nitriles;Phenyls & Phenyl-Het;Nitrile;Nitriles;Miscellaneous;Bromine Compounds;Phenyls & Phenyl-Het;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Indazoles
• Mol File: 2042-37-7.mol
• Article Data: 91

Chemical Properties

• Melting Point: 53-57 °C(lit.)
• Boiling Point: 251-253 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow/Crystalline Solid
• Density: 1.496
• Vapor Pressure: 0.0198mmHg at 25°C
• Refractive Index: 1.5999 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 10.5g/l
• BRN: 2042185
• CAS DataBase Reference: 2-Bromobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzonitrile(2042-37-7)
• EPA Substance Registry System: 2-Bromobenzonitrile(2042-37-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26
• RIDADR: 3276
• WGK Germany: 2
• RTECS: DI2459750
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2042-37-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2-Bromobenzonitrile belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.

InChI:InChI=1/C7H4BrN/c8-7-4-2-1-3-6(7)5-9/h1-4H

Synthetic route

2-bromobenzaldehyde oxime (34158-72-0, 52707-51-4, 52707-56-9) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester; triethylamine In acetonitrile at 20℃; for 0.583333h;	98%
With oxalyl dichloride; Tropone; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 0.25h; Schlenk technique; Inert atmosphere;	98%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 1h; Swern Oxidation;	93%

2-methylphenyl bromide (95-46-5) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
Stage #1: 2-methylphenyl bromide With hydrogen bromide; dihydrogen peroxide In tetrachloromethane; water at 20℃; for 1h; Irradiation; Stage #2: With ammonia; iodine In tetrachloromethane; water; acetonitrile at 20 - 60℃; for 24h;	97%
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 70℃; for 24h; Inert atmosphere; Sealed tube;	80%
Stage #1: 2-methylphenyl bromide With sodium azide; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; zinc trifluoromethanesulfonate In acetonitrile at 25℃; Irradiation; Stage #2: With trifluorormethanesulfonic acid In acetonitrile for 1h;	51%

2-bromo-6-iodobenzonitrile → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With formic acid; tributyl-amine; 1,1′-(10-(4-acetylphenyl)-10H-phenothiazine-3,7-diyl)bis(ethan-1-one) In acetonitrile at 23℃; for 24h; UV-irradiation; chemoselective reaction;	97%

2-Bromobenzamide (4001-73-4) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h;	95%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.666667h; Swern Oxidation;	95%
With C36H38Cl6N6Pd3S2 In water; acetonitrile at 80℃; for 6h; Reagent/catalyst;	78%

ortho-bromophenylacetic acid (18698-97-0) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 26h; Green chemistry;	95%

ortho-bromobenzaldehyde (6630-33-7) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With ammonium acetate; phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 15h;	94%
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;	93%
With ammonium iodide In dimethyl sulfoxide at 20℃; for 4h; Electrolysis;	91%

o-bromobenzyl alcohol (18982-54-2) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Phenylglycine; sodium hydroxide In methanol at 100℃; for 18h; Cooling with ice;	90%
With ammonia; oxygen In tert-Amyl alcohol; water at 130℃; under 3750.38 Torr; for 24h;	90%
Stage #1: o-bromobenzyl alcohol With sodium azide; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; zinc trifluoromethanesulfonate In acetonitrile at 25℃; Irradiation; Stage #2: With trifluorormethanesulfonic acid In acetonitrile for 1h;	73%
Multi-step reaction with 3 steps 1: potassium carbonate; fluorosulfonyl fluoride; dimethyl sulfoxide / 12 h / 20 °C 2: hydroxylamine hydrochloride; potassium carbonate / 20 °C 3: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C View Scheme

anthranilic acid nitrile (1885-29-6) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
Stage #1: anthranilic acid nitrile With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h; Stage #2: With acetic acid In dichloromethane; water at 23℃; for 1h;	89%
With tetrabutylammomium bromide; 10-camphorsulfonic acid; sodium nitrite In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;	78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;	75%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide	68%

2-(2-bromo-phenyl)[1,3,4]oxadiazole (928722-52-5) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 4h;	88%

1-Bromo-2-iodobenzene (583-55-1) + potassium ferrocyanide → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;	88%
With 3% Au/CeO2; sodium carbonate In dimethyl sulfoxide; isopropyl alcohol at 65℃; for 12h; Irradiation;	83%

benzonitrile (100-47-0) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With N-Bromosuccinimide; palladium diacetate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 70℃; for 12h; Sealed tube;	87%

2-bromobenzylamine (3959-05-5) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;	85.4%
With potassium hydroxide; dipotassium peroxodisulfate; ruthenium trichloride In water for 1.5h;	83%
With isoquinoline; oxygen; copper; ammonium bromide In toluene at 100℃; under 760.051 Torr; for 24h; Green chemistry;	64.9 %Chromat.
With ammonia; oxygen; silica gel; 11-pyridino[3,2-h]quinoxalino[2,3-f]quinolin-11-ylpyridino[3,2-h]quinoxalino[2,3-f]quinoline In tert-Amyl alcohol; N,N-dimethyl-formamide at 110 - 800℃; under 1500.15 Torr; for 16h; Sonication; Inert atmosphere; Calcination;	73.27 %Chromat.

2-bromobenzaldehyde oxime (34158-72-0, 52707-51-4, 52707-56-9) + 1,3-diphenyl-2-propynone (7338-94-5) → 3-hydroxy-1,3-diphenyl-2-propen-1-one (1704-15-0, 62961-62-0) + o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With triphenylphosphine In dichloromethane at 25℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube;	A 88 %Spectr. B 85%

2-cyano-benzenediazonium tetrafluoroborate (55165-45-2) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;	84%

2-<(trifluoromethanesulfonyl)oxy>benzonitrile (138313-23-2) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere;	83%

2-bromobenzylamine hydrochloride (5465-63-4) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With cis-[Os(VIII)O4(OH)2](2-); [Fe(CN)6](3-); acetonitrile at 20℃; for 1.5h;	82%

2,2-dimethylmalononitrile (7321-55-3) + 1-Bromo-2-iodobenzene (583-55-1) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
Stage #1: 1-Bromo-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 23℃; for 3h;	82%

benzonitrile (100-47-0) → 3-cyanobromobenzene (6952-59-6) + o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With bromine fluoride In ethanol; chloroform at -40℃; for 0.25h;	A 81% B 10%
With bromine trifluoride; bromine at 0 - 10℃;	A 45% B 12%

2-bromostyrene (2039-88-5) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With formic acid; sodium nitrite In acetonitrile at 70℃; for 4h; Schlenk technique;	78%
With formic acid; 5,10,15,20‐tetrakis‐(4‐sulfonatophenyl)‐porphyrin‐iron(III) chloride; sodium nitrite In acetonitrile at 70℃; for 4.5h;	78.49%
With [bis(acetoxy)iodo]benzene; ammonium bicarbonate In methanol; water at 36℃; for 12h; Sealed tube;	65%

2-bromo-N-(isopropyl)benzamide (64141-90-8) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 30℃; for 12h; chemoselective reaction;	77%

ortho-bromobenzaldehyde (6630-33-7) → o-cyanobromobenzene (2042-37-7) + 2-Bromobenzamide (4001-73-4)

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 n/a B 76%

2-bromobenzoic-acid (88-65-3) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With aluminum oxide; aminosulfonic acid; urea for 0.216667h; Irradiation;	75%
Multi-step reaction with 3 steps 1: thionyl chloride 2: aqueous ammonia 3: thionyl chloride View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / 21 h / Inert atmosphere; Reflux 2.1: sodium diisobutyl-tert-butoxyaluminium hydride / tetrahydrofuran / 4 h / -40 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere View Scheme

2-bromophenyl methyl ketone (2142-69-0) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With oxygen; copper diacetate; ammonium carbonate; tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide at 120℃; for 5h; Schlenk technique;	70%

2-bromobenzylamine (3959-05-5) → o-cyanobromobenzene (2042-37-7) + ortho-bromobenzaldehyde (6630-33-7)

Conditions	Yield
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 1.5h;	A 68% B 6 %Chromat.

2-bromobenzylamine (3959-05-5) → o-cyanobromobenzene (2042-37-7) + 2-Bromobenzamide (4001-73-4)

Conditions	Yield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 16h;	A 64.1% B 28.1%

potassiumhexacyanoferrate(II) trihydrate + 1,2-dibromobenzene (583-53-9) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 20h;	64%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2-bromoaniline (615-36-1) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With acetic acid; sodium nitrite In neat (no solvent) at 50℃; for 1h;	55%

2-bromo-1-ethynylbenzene (766-46-1) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With tert.-butylnitrite; benzyl-methyl-amine In dimethyl sulfoxide at 110℃; for 12h;	54%

ethyl 2-azido-2-(2-bromophenyl)acetate (1221966-47-7) → o-cyanobromobenzene (2042-37-7)

Conditions	Yield
With oxygen; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 60℃; under 760.051 Torr;	47%

o-cyanobromobenzene (2042-37-7) + 3',5'-Di-tert-butyl-2'-hydroxy-biphenyl-2-carbonitrile → 2,4-di-tert-butyldibenzopyran-6-one

Conditions	Yield
With silica gel In dichloromethane Ambient temperature;	100%

o-cyanobromobenzene (2042-37-7) + phenylboronic acid (98-80-6) → biphenyl-2-carbonitrile (24973-49-7)

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium phosphate; (dppf)Ni(o-tol)Cl In 1,4-dioxane at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Sealed tube;	100%
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.1h; Suzuki cross-coupling reaction;	99%

o-cyanobromobenzene (2042-37-7) + 4-methylphenylboronic acid (5720-05-8) → 2-Cyano-4'-methylbiphenyl (114772-53-1)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 50℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium carbonate; [1-cyclohexyl-3-(di-pyridin-2-yl-methyl)-urea][PdCl2] In water at 100℃; for 1h; Suzuki-Miyaura coupling;	99%
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Suzuki cross-coupling reaction;	99%

o-cyanobromobenzene (2042-37-7) + 4-methoxyphenylacetylen (768-60-5) → 2-(2-(4-methoxyphenyl)ethynyl)benzonitrile (351862-56-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere;	83%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 2h; Inert atmosphere;

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (425378-68-3) + o-cyanobromobenzene (2042-37-7) → 2'-fluoro-5'-nitrobiphenyl-2-carbonitrile (425378-69-4)

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; 1,4-dioxane at 20 - 50℃; for 1.5h;	100%
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20 - 50℃;

o-cyanobromobenzene (2042-37-7) + o-fluorophenylboronic acid (1993-03-9) → 2'-fluoro-[1,1'-biphenyl]-2-carbonitrile (400820-15-7)

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; 1,4-dioxane at 20 - 50℃; for 0.75h;	100%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 150℃; for 0.5h; Suzuki cross-coupling; microwave irradiation;	88%
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate In N,N-dimethyl-formamide at 150℃; for 0.5h; Suzuki coupling; Inert atmosphere; Microwave irradiation;	81%

o-cyanobromobenzene (2042-37-7) + zinc (7440-66-6) → biphenyl-2,2'-dicarbonitrile (4341-02-0) + benzonitrile (100-47-0) + 2-cyanophenylzinc bromide (131379-17-4)

Conditions	Yield
With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide In acetonitrile the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;	A 0% B 0% C 100%

o-cyanobromobenzene (2042-37-7) + 4-tert-butylphenylboronic acid (123324-71-0) → 4'-(tert-butyl)-[1,1'-biphenyl]-2-carbonitrile

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0833333h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;	100%
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling;	67%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0333333h; Catalytic behavior; Suzuki-Miyaura Coupling;	100 %Chromat.
With potassium carbonate In water; isopropyl alcohol at 80℃; for 0.5h; Suzuki-Miyaura Coupling;	45 %Chromat.

o-cyanobromobenzene (2042-37-7) + 2-Methylphenylboronic acid (16419-60-6) → 2-(o-Tolyl)benzonitrile (157366-46-6)

Conditions	Yield
With sodium tetrachloropalladate(II); 5-[3-(4-carboxy-2,6-dimethylphenyl)-2-thioxoimidazolidin-1-yl]benzene-1,2,3-tricarboxylic acid; tetrabutylammomium bromide; potassium hydroxide In water at 20℃; for 48h; Suzuki-Miyaura Coupling; Sealed tube;	99%
With Pd/C; diisopropylamine In water at 100℃; for 3h; Suzuki Coupling; Green chemistry;	98%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene at 80℃; Suzuki-Miyaura cross coupling reaction; Inert atmosphere;	94%

o-cyanobromobenzene (2042-37-7) + 4-methoxyphenylboronic acid (5720-07-0) → 4'-methoxybiphenyl-2-carbonitrile (125610-78-8)

Conditions	Yield
With potassium phosphate; [5-(3-butylbenzimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxy calix[4]arene] (pyridine) palladium(II) dibromide In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	99%
With potassium carbonate In water at 80℃; for 10h; Suzuki-Miyaura Coupling; Green chemistry;	95%
Stage #1: 4-methoxyphenylboronic acid With potassium phosphate; 2C2F6NO4S2(1-)*C44H66Cl2N2P2Pd(2+); 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide In water at 65℃; Suzuki-Miyaura reaction; Inert atmosphere; Stage #2: o-cyanobromobenzene In water at 65℃; for 2h; Suzuki-Miyaura reaction; Inert atmosphere;	92%
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100℃; Suzuki-Miyaura coupling; Inert atmosphere;	91%
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling;	68%

o-cyanobromobenzene (2042-37-7) → 2-bromobenzylamine hydrochloride (5465-63-4)

Conditions	Yield
Stage #1: o-cyanobromobenzene 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: o-cyanobromobenzene With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃;	98%
Stage #1: o-cyanobromobenzene With 1,1,3,3-Tetramethyldisiloxane; titanium(IV)isopropoxide In methyl cyclohexane at 60℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride; water In methyl cyclohexane at 20℃; Inert atmosphere;	98%

benzophenone hydrazone (5350-57-2) + o-cyanobromobenzene (2042-37-7) → 2-(2-(diphenylmethylene)hydrazinyl)benzonitrile (1219024-53-9)

Conditions	Yield
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.05h; Inert atmosphere; Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 20 - 100℃; for 7h; Inert atmosphere;	99%
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.25h; Inert atmosphere; Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 100℃; for 43h; Inert atmosphere;	74%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 12h; Inert atmosphere;

o-cyanobromobenzene (2042-37-7) + isopropyl zinc bromide (77047-87-1) → 2-Isopropyl-1-benzonitrile (40751-52-8)

Conditions	Yield
With [1,3-bis(2,6-diisoheptylphenyl)-4,5-dichloroimidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride In tetrahydrofuran; toluene at 0 - 23℃; Reagent/catalyst; Negishi Coupling; Inert atmosphere; Schlenk technique;	99%
Stage #1: o-cyanobromobenzene With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice; Stage #2: isopropyl zinc bromide In tetrahydrofuran; toluene at 23℃; for 0.5h; Inert atmosphere;	76%

o-cyanobromobenzene (2042-37-7) + phenol (108-95-2) → o-phenoxybenzonitrile (6476-32-0)

Conditions	Yield
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique;	99%
With copper(II) oxide; potassium hydroxide In N,N-dimethyl acetamide at 27℃; for 24h; Ullmann Condensation; Inert atmosphere; Sealed tube;	61%

o-cyanobromobenzene (2042-37-7) + cyclopentylzinc bromide lithium chloride → 2-cyclo-pentylbenzonitrile (221626-03-5)

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

o-cyanobromobenzene (2042-37-7) + 3-formyl-4-methoxyphenylboronic acid → 3'-formyl-4'-methoxybiphenyl-2-carbonitrile

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0166667h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;	99%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.05h; Catalytic behavior; Suzuki-Miyaura Coupling;	94 %Chromat.
With potassium carbonate In water; isopropyl alcohol at 80℃; for 0.5h; Suzuki-Miyaura Coupling;	65 %Chromat.

o-cyanobromobenzene (2042-37-7) + phenylmanganese(II) chloride (71478-47-2) → biphenyl-2-carbonitrile (24973-49-7)

Conditions	Yield
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 3h;	98%

o-cyanobromobenzene (2042-37-7) + 4-methoxyphenylmagnesium chloride (699-19-4) → 4'-methoxybiphenyl-2-carbonitrile (125610-78-8)

Conditions	Yield
Stage #1: 4-methoxyphenylmagnesium chloride With 2-iodo-propane In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: o-cyanobromobenzene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In tetrahydrofuran at 25℃; for 0.0833333h; Kumada coupling reaction; Inert atmosphere;	98%
Stage #1: 4-methoxyphenylmagnesium chloride With N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In tetrahydrofuran at 80℃; for 0.25h; microwave irradiation; Stage #2: o-cyanobromobenzene; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 120℃; for 0.0333333h; Negishi cross-coupling; microwave irradiation;	92%

o-cyanobromobenzene (2042-37-7) + 3-Aminophenylboronic acid (30418-59-8) → 3'-aminobiphenyl-2-carbonitrile (342613-84-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 80℃; for 20h; Suzuki coupling;	98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 80℃; for 20h;	98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 20h;	98%

o-cyanobromobenzene (2042-37-7) + 3-aminobenzeneboronic acid monohydrate → 3'-aminobiphenyl-2-carbonitrile (342613-84-7) + 3'-(7-Formylimidazo[1,2-α]pyridin-3-yl)bilphenyl-2-carbonitrile

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetate	A n/a B 98%

o-cyanobromobenzene (2042-37-7) → 2-Bromobenzamide (4001-73-4)

Conditions	Yield
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 50℃; for 48h;	98%
With Wilkinson's catalyst; Acetaldehyde oxime In toluene at 110℃;	90%
With Wilkinson's catalyst; Acetaldehyde oxime In toluene at 110℃; for 4h;	90%

o-cyanobromobenzene (2042-37-7) + 2-fluoro-3-(trimethylsilanyl)phenylboronic Acid (1410703-15-9) → 2′-fluoro-3′-(trimethylsilanyl)biphenyl-2-carbonitrile (1410703-17-1)

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 90℃; for 14h; Inert atmosphere;	98%

bromoacetic acid tert-butyl ester (5292-43-3) + o-cyanobromobenzene (2042-37-7) → (2-cyanophenyl)acetic acid tert-butyl ester

Conditions	Yield
Stage #1: bromoacetic acid tert-butyl ester With zinc In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Stage #2: o-cyanobromobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Sealed tube;	98%

o-cyanobromobenzene (2042-37-7) + 2-mercaptoethylamine hydrochloride (156-57-0) → 2-(2-bromophenyl)-4,5-dihydrothiazole

Conditions	Yield
With sodium hydroxide In neat (no solvent) at 80℃; for 1.5h;	98%

NH-pyrazole (288-13-1) + o-cyanobromobenzene (2042-37-7) → 2-(1H-pyrazol-1-yl)-benzonitrile (25775-03-5)

Conditions	Yield
With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere;	98%
With quebrachitol; copper; caesium carbonate In water; dimethyl sulfoxide at 110℃; for 24h; Ullmann Condensation; Inert atmosphere; Green chemistry;	89%
With D-galacturonic acid; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 80 - 100℃; Inert atmosphere; Green chemistry;	87%
With copper(I) oxide; caesium carbonate; N-phenyl-2-pyridincarboxamide-1-oxide In dimethyl sulfoxide at 120℃; for 20h; Catalytic behavior; Solvent; Temperature; Inert atmosphere;	70%

o-cyanobromobenzene (2042-37-7) + 3-aminobenzeneboronic acid monohydrate → 3'-aminobiphenyl-2-carbonitrile (342613-84-7) + 3'-(7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetate	A n/a B 98%

o-cyanobromobenzene (2042-37-7) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan (402503-13-3) → 2-(2-benzofuranyl)-benzonitrile (121668-44-8)

Conditions	Yield
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 12h; Suzuki-Miyaura Coupling;	98%

benzaldehyde p-toluenesulfonylhydrazone (1666-17-7) + o-cyanobromobenzene (2042-37-7) → 4-(2-bromophenyl)-5-phenyl-2H-1,2,3-triazole (120106-68-5)

Conditions	Yield
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 4h; Inert atmosphere;	98%

1-[(4-methoxyphenyl)sulfanyl]pyrrolidine-2,5-dione (80172-73-2) + o-cyanobromobenzene (2042-37-7) → 2-((4-methoxyphenyl)thio)benzonitrile (128958-95-2)

Conditions	Yield
With N,N,N'N'-tetramethyl-1,3-propanediamine; trimethoxonium tetrafluoroborate; copper(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In acetonitrile at 80℃; for 3h; Reagent/catalyst;	97.7%

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 88-65-3 2-bromobenzoic-acid 
• 127099-85-8 N-Cyanoguanidine 
• 100-47-0 benzonitrile 
• 7664-93-9 sulfuric acid 
• 52707-56-9 Z-2-bromo-benzaldehyde-oxime 
• 108-24-7 acetic anhydride 
• 17333-81-2 o-bromobenzenediazonium 
• 6630-33-7 ortho-bromobenzaldehyde 
• 3959-05-5 2-bromobenzylamine 
• 1221966-47-7 ethyl 2-azido-2-(2-bromophenyl)acetate 
• 70-11-1 α-bromoacetophenone 
• 158918-49-1 N’-(2-bromobenzylidene)-4-methylbenzenesulfonohydrazide 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 294878-57-2 (2-bromophenyl)(o-tolyl)methanone 
• 2142-69-0 2-bromophenyl methyl ketone 
• 36081-66-0 2'-bromo-2-phenylacetophenone 
• 693208-77-4 2-Bromphenylbenzyl-ketimin 
• 131379-35-6 ethyl 2′-cyano-[1,1′-biphenyl]-3-carboxylate 
• 34761-11-0 2-cyanothiophenol 
• 63216-04-6 o-benzyl mercapto-benzonitrile 
• 86369-35-9 cyano acetic acid ethyl ester 
• 110166-78-4 2-(hex-1-yn-1-yl)benzonitrile 
• 64633-76-7 o-ethylmercapto-benzonitrile 
• 89407-26-1 o-(hydroxy-2-ethyl)mercapto-benzonitrile 
• 50620-99-0 alpha-cyanocinnamic acid ethyl ester 
• 873-32-5 2-Chlorobenzonitrile 
• 4387-36-4 2-iodobenzonitrile 

Relevant articles and documents

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Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.