2-bromobenzaldehyde oxime
o-cyanobromobenzene
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% |
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% |
o-cyanobromobenzene
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% |
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
o-cyanobromobenzene
Conditions | Yield |
---|---|
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 26h; Green chemistry; | 95% |
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
o-cyanobromobenzene
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 |
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
o-cyanobromobenzene
Conditions | Yield |
---|---|
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 4h; | 88% |
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% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; palladium diacetate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 70℃; for 12h; Sealed tube; | 87% |
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
1,3-diphenyl-2-propynone
A
3-hydroxy-1,3-diphenyl-2-propen-1-one
B
o-cyanobromobenzene
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
o-cyanobromobenzene
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
o-cyanobromobenzene
Conditions | Yield |
---|---|
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With cis-[Os(VIII)O4(OH)2](2-); [Fe(CN)6](3-); acetonitrile at 20℃; for 1.5h; | 82% |
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% |
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% |
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
o-cyanobromobenzene
Conditions | Yield |
---|---|
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 30℃; for 12h; chemoselective reaction; | 77% |
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% |
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 |
Conditions | Yield |
---|---|
With oxygen; copper diacetate; ammonium carbonate; tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide at 120℃; for 5h; Schlenk technique; | 70% |
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. |
Conditions | Yield |
---|---|
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 16h; | A 64.1% B 28.1% |
Conditions | Yield |
---|---|
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 20h; | 64% |
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite In neat (no solvent) at 50℃; for 1h; | 55% |
Conditions | Yield |
---|---|
With tert.-butylnitrite; benzyl-methyl-amine In dimethyl sulfoxide at 110℃; for 12h; | 54% |
ethyl 2-azido-2-(2-bromophenyl)acetate
o-cyanobromobenzene
Conditions | Yield |
---|---|
With oxygen; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 60℃; under 760.051 Torr; | 47% |
o-cyanobromobenzene
Conditions | Yield |
---|---|
With silica gel In dichloromethane Ambient temperature; | 100% |
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
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
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
4-methoxyphenylacetylen
2-(2-(4-methoxyphenyl)ethynyl)benzonitrile
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
o-cyanobromobenzene
2'-fluoro-5'-nitrobiphenyl-2-carbonitrile
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
o-fluorophenylboronic acid
2'-fluoro-[1,1'-biphenyl]-2-carbonitrile
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
zinc
A
biphenyl-2,2'-dicarbonitrile
B
benzonitrile
C
2-cyanophenylzinc bromide
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
4-tert-butylphenylboronic acid
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
2-Methylphenylboronic acid
2-(o-Tolyl)benzonitrile
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
4-methoxyphenylboronic acid
4'-methoxybiphenyl-2-carbonitrile
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% |
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
o-cyanobromobenzene
2-(2-(diphenylmethylene)hydrazinyl)benzonitrile
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
isopropyl zinc bromide
2-Isopropyl-1-benzonitrile
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% |
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
2-cyclo-pentylbenzonitrile
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
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
phenylmanganese(II) chloride
biphenyl-2-carbonitrile
Conditions | Yield |
---|---|
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 3h; | 98% |
o-cyanobromobenzene
4-methoxyphenylmagnesium chloride
4'-methoxybiphenyl-2-carbonitrile
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
3-Aminophenylboronic acid
3'-aminobiphenyl-2-carbonitrile
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
A
3'-aminobiphenyl-2-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetate | A n/a B 98% |
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
2-fluoro-3-(trimethylsilanyl)phenylboronic Acid
2′-fluoro-3′-(trimethylsilanyl)biphenyl-2-carbonitrile
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 90℃; for 14h; Inert atmosphere; | 98% |
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In neat (no solvent) at 80℃; for 1.5h; | 98% |
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
A
3'-aminobiphenyl-2-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetate | A n/a B 98% |
o-cyanobromobenzene
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan
2-(2-benzofuranyl)-benzonitrile
Conditions | Yield |
---|---|
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 12h; Suzuki-Miyaura Coupling; | 98% |
benzaldehyde p-toluenesulfonylhydrazone
o-cyanobromobenzene
4-(2-bromophenyl)-5-phenyl-2H-1,2,3-triazole
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
o-cyanobromobenzene
2-((4-methoxyphenyl)thio)benzonitrile
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% |
The 2-Bromobenzonitrile is an organic compound with the formula C7H4BrN. The IUPAC name of this chemical is 2-bromobenzonitrile. With the CAS registry number 2042-37-7, it is also named as Benzonitrile, 2-bromo-. The product's categories are 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. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place.
The 2-Bromobenzonitrile can be used as the intermediates in organic synthesis. Besides, it can also be mainly used in cereal, flax, garlic, corn, onion, sorghum and new grass seed at the seedling stage. Mixed with other herbicides, it can expand the weed spectrum.
Physical properties about 2-Bromobenzonitrile are: (1)ACD/LogP: 2.23; (2)ACD/LogD (pH 5.5): 2.23; (3)ACD/LogD (pH 7.4): 2.23; (4)ACD/BCF (pH 5.5): 28.99; (5)ACD/BCF (pH 7.4): 28.99; (6)ACD/KOC (pH 5.5): 387.54; (7)ACD/KOC (pH 7.4): 387.54; (8)#H bond acceptors: 1; (9)Polar Surface Area: 23.79 Å2; (10)Index of Refraction: 1.606; (11)Molar Refractivity: 39.04 cm3; (12)Molar Volume: 113.1 cm3; (13)Polarizability: 15.47×10-24cm3; (14)Surface Tension: 52.1 dyne/cm; (15)Density: 1.6 g/cm3; (16)Flash Point: 113.7 °C; (17)Enthalpy of Vaporization: 48.93 kJ/mol; (18)Boiling Point: 252 °C at 760 mmHg; (19)Vapour Pressure: 0.0198 mmHg at 25°C.
Preparation: this chemical can be prepared by benzonitrile. This reaction will need reagent BrF3, Br2. The reaction temperature is 0 - 10 °C. The yield is about 45%.
Uses of 2-Bromobenzonitrile: it can be used to produce 5-(2-bromo-phenyl)-1(2)H-tetrazole. It will need reagent acetic acid, butan-1-ol, NaN3.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection, do not breathe dust and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1ccccc1Br
(2)InChI: InChI=1/C7H4BrN/c8-7-4-2-1-3-6(7)5-9/h1-4H
(3)InChIKey: AFMPMSCZPVNPEM-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C7H4BrN/c8-7-4-2-1-3-6(7)5-9/h1-4H
(5)Std. InChIKey: AFMPMSCZPVNPEM-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 300mg/kg (300mg/kg) | Journal of Medicinal Chemistry. Vol. 21, Pg. 906, 1978. |
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