2-Chlorobenzonitrile
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In n-heptane; water at 60℃; for 1.66667h; Suzuki Coupling; Inert atmosphere; | 100% |
With potassium carbonate In water; isopropyl alcohol at 100℃; for 7h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere; | 100% |
With bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide; tetra(n-butyl)ammonium hydroxide; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 0.666667h; Suzuki-Miyaura coupling; Microwave irradiation; | 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% |
Conditions | Yield |
---|---|
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; TPGS-750-M; triethylamine In water at 40℃; Inert atmosphere; | 99% |
With potassium carbonate In ethanol; water at 120℃; for 2.5h; Suzuki-Miyaura reaction; continuous flow reactor; | 54% |
2-Chlorobenzonitrile
para-methylphenylmagnesium bromide
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 17h; Schlenk technique; Inert atmosphere; | 98% |
Stage #1: para-methylphenylmagnesium bromide With zinc(II) chloride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: 2-Chlorobenzonitrile With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Negishi reaction; Further stages.; | 97% |
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere; | 85% |
2-Chlorobenzonitrile
4'-methyl-2-acetyl-1,1'-biphenyl
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With cesium fluoride; Pd(dba)2 In 1,4-dioxane | 98% |
2-Chlorobenzonitrile
di(p-tolyl)borinic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With NiCl2(Tris-(4-methoxy-phenyl)-phosphin)2; potassium phosphate tribasic trihydrate; P(p-CH3OC6H4)3 In toluene at 110℃; for 5h; Reagent/catalyst; Inert atmosphere; | 98% |
With triphenyl phosphite; potassium phosphate tribasic trihydrate; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; palladium diacetate In tert-butyl alcohol at 80℃; for 16h; Inert atmosphere; | 97% |
With bis(triphenylphosphine)nickel(II) chloride; potassium phosphate tribasic trihydrate; 1-n-butyl-3-methylimidazolim bromide In toluene at 110℃; for 6h; Inert atmosphere; | 97% |
o-cyanobromobenzene
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; oxygen; potassium carbonate In ethanol; water at 80℃; for 0.416667h; Suzuki-Miyaura Coupling; | 97% |
With palladium diacetate; potassium carbonate In ethanol; water at 25℃; for 2h; Suzuki-Miyaura Coupling; | 95% |
4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate at 100℃; for 3h; | 96% |
With pyridine; trichlorophosphate at 10 - 100℃; for 3h; | |
Multi-step reaction with 2 steps 1: hydrogenchloride 2: thionyl chloride / water; toluene View Scheme |
o-cyanobromobenzene
4-tolylmagnesium chloride
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With 1,2-dimethoxyethane; Cl4Li2Pd; 1,3-bis-(diphenylphosphino)propane | 95% |
With 1,2-dimethoxyethane; lithium chloride; manganese(ll) chloride; 1,3-bis-(diphenylphosphino)propane; palladium dichloride In tetrahydrofuran at 20℃; for 1 - 3.5h; | 95% |
With 1,2-dimethoxyethane; 1,3-bis-(diphenylphosphino)propane; palladium diacetate | 94% |
2-Chlorobenzonitrile
sodium 4-methylbenzenesulfinate
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With palladium diacetate; XPhos In toluene at 120℃; for 40h; Inert atmosphere; Sealed tube; | 95% |
2-Chlorobenzonitrile
p-tolylzinc(II) chloride
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine)nickel(0) Negishi-like coupling reaction; | 94% |
With C26H24ClN2NiP*0.1C7H8 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Negishi Coupling; Schlenk technique; Inert atmosphere; | 92% |
tris(dibenzylideneacetone)dipalladium (0); tris[tert-butyl]phosphonium tetrafluoroborate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 175℃; for 0.166667h; Negishi cross-coupling; microwave irradiation; | 90% |
With C21H18N8Ni2O(2+)*2F6P(1-) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20 - 80℃; Negishi coupling reaction; | 88% |
Conditions | Yield |
---|---|
Stage #1: para-chlorotoluene With magnesium In tetrahydrofuran at 50 - 70℃; Inert atmosphere; Stage #2: 2-Chlorobenzonitrile With magnesium chloride In tetrahydrofuran at 5 - 10℃; Inert atmosphere; | 93.6% |
o-cyanobromobenzene
4-tolylmagnesium chloride
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; 1,2-dimethoxyethane | 93% |
Conditions | Yield |
---|---|
Stage #1: p-toluidine With toluene-4-sulfonic acid; sodium nitrite In water at 25℃; Stage #2: benzonitrile With copper(l) iodide; sodium acetate In water at 80℃; Solvent; Temperature; Reagent/catalyst; | 92.1% |
Stage #1: p-toluidine With tetrafluoroboric acid; sodium nitrite In water at 0 - 5℃; for 0.5h; Inert atmosphere; Stage #2: benzonitrile With Tetrakis(dimethylamino)ethylen; 9-methylamino-1-ethoxyphenalenium tetrafluoroborate In dimethyl sulfoxide at 20℃; for 12h; Glovebox; Inert atmosphere; regioselective reaction; | 50% |
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With phosphorus pentoxide In tetrahydrofuran at 20℃; for 1h; | 92% |
Conditions | Yield |
---|---|
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; TPGS-750-M; triethylamine In water at 20℃; Inert atmosphere; | 92% |
With Pd/Nb2O5; potassium carbonate In ethanol; water at 120℃; for 2h; Suzuki-Miyaura cross-coupling; Microwave irradiation; |
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With C26H16Cl6N2O2Pd2; tetrabutylammomium bromide; potassium hydroxide In methanol; water at 110℃; for 0.333333h; Suzuki coupling; Microwave irradiation; | 92% |
o-cyanobromobenzene
tributyl(p-tolyl)stannane
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; diisopropylamine In ethanol; water at 25℃; for 4h; | 92% |
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With formic acid | 91% |
2-iodobenzonitrile
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With potassium phosphate Reflux; | 90.4% |
With sodium carbonate In water; ethyl acetate; isopropyl alcohol at 50℃; for 0.00111111h; Suzuki-Miyaura coupling; Microchannel flow reactor; | 99 %Chromat. |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide for 6h; Suzuki Coupling; Inert atmosphere; Reflux; |
2-Chlorobenzonitrile
4-tolylmagnesium chloride
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
Stage #1: 2-Chlorobenzonitrile With bis(triphenylphosphine)nickel(II) chloride; methoxydichlorozinc acid In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 4-tolylmagnesium chloride In tetrahydrofuran at 28 - 32℃; Inert atmosphere; | 90% |
Stage #1: 2-Chlorobenzonitrile With chloro-trimethyl-silane; manganese(ll) chloride In tetrahydrofuran at -5 - 0℃; Inert atmosphere; Green chemistry; Stage #2: 4-tolylmagnesium chloride In tetrahydrofuran at -5 - 25℃; for 9h; Inert atmosphere; Green chemistry; | 86% |
With nickel; zinc(II) chloride In tetrahydrofuran at 50 - 60℃; Product distribution; various double metal catalysts, various yield of products; | |
With iron(III) chloride In tetrahydrofuran at 0 - 130℃; for 3h; Temperature; Grignard Reaction; Large scale; | 6.93 kg |
sodium 4-methylbenzenesulfinate
2-<(trifluoromethanesulfonyl)oxy>benzonitrile
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With palladium diacetate; XPhos In toluene at 120℃; for 24h; Sealed tube; Inert atmosphere; | 90% |
o-cyanobromobenzene
sodium 4-methylbenzenesulfinate
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With palladium diacetate; XPhos In toluene at 120℃; for 40h; Inert atmosphere; Sealed tube; | 90% |
With caesium carbonate; palladium dichloride In N,N-dimethyl-formamide at 185℃; for 20h; Inert atmosphere; Sealed tube; | 54% |
Conditions | Yield |
---|---|
With Ti0.97Pd0.03O1.97; potassium carbonate In water at 100℃; for 6h; Suzuki-Miyaura Coupling; | 89% |
Conditions | Yield |
---|---|
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane | 88% |
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane | 88% |
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane | 88% |
Conditions | Yield |
---|---|
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane | 88% |
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; hexane; ethyl acetate; pentane | |
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; hexane; ethyl acetate; pentane |
o-cyanobromobenzene
4-tolylmagnesium chloride
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran; water; toluene | 88% |
para-bromotoluene
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
Stage #1: para-bromotoluene With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 25℃; for 24h; Knochel Zinc Vinyl Coupling; Inert atmosphere; Stage #2: 2-(cyano)halobenzene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In tetrahydrofuran at 25℃; for 1h; Knochel Zinc Vinyl Coupling; Inert atmosphere; Schlenk technique; | 88% |
2-Chlorobenzonitrile
4-methylphenylboronic acid
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
With cesium fluoride In 1,4-dioxane | 87% |
2-Cyano-4'-methylbiphenyl
2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With trimethylsilylazide; tetrabutyl ammonium fluoride at 120℃; for 36h; | 97% |
With sodium azide; zinc(II) chloride In N,N-dimethyl-formamide for 36h; Heating; | 96% |
With sodium azide; triethylamine hydrochloride In N,N-dimethyl-formamide at 35℃; for 3h; Temperature; Sonication; | 96% |
2-Cyano-4'-methylbiphenyl
Conditions | Yield |
---|---|
Stage #1: 2-Cyano-4'-methylbiphenyl With dirhodium tetraacetate In chloroform at 70℃; Stage #2: methyl 2-diazo-2-(fluorosulfonyl)acetate In chloroform at 70℃; for 12h; | 97% |
2-Cyano-4'-methylbiphenyl
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane | 96% |
With bromine In water; 1,2-dichloro-ethane at 84℃; for 0.25h; Temperature; Solvent; Irradiation; Flow reactor; | 96.3% |
With bromine In 1,2-dichloro-ethane at 70℃; for 0.5h; Reagent/catalyst; Temperature; Time; Irradiation; | 94% |
2-Cyano-4'-methylbiphenyl
5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole
Conditions | Yield |
---|---|
Stage #1: 2-Cyano-4'-methylbiphenyl With sodium azide; zinc(II) chloride In N,N-dimethyl-formamide for 36h; Heating; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide for 1h; cooling; Further stages.; | 96% |
With hydrogenchloride; sodium azide; triethylamine hydrochloride In 5,5-dimethyl-1,3-cyclohexadiene at 28 - 142℃; for 29h; | 87% |
Stage #1: 2-Cyano-4'-methylbiphenyl With sodium azide In N,N-dimethyl-formamide at 135℃; for 37h; Stage #2: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide | 82% |
2-Cyano-4'-methylbiphenyl
4-Methylbiphenyl-2'-carboxamidoxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In methanol; dimethyl sulfoxide | 96% |
With hydroxylamine hydrochloride; triethylamine In dimethyl sulfoxide at 80 - 85℃; for 24h; Reagent/catalyst; Solvent; | 89.6% |
2-Cyano-4'-methylbiphenyl
2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl
Conditions | Yield |
---|---|
Zinc chloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide | 94% |
2-Cyano-4'-methylbiphenyl
o-(p-tolyl)-benzylamine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-Cyano-4'-methylbiphenyl With C46H178O41Si42; titanium(IV)isopropoxide In toluene at 60℃; for 9h; Inert atmosphere; Stage #2: With hydrogenchloride; water In toluene at 20℃; for 9h; Inert atmosphere; | 94% |
2-Cyano-4'-methylbiphenyl
o-tolylbenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethylene glycol at 170℃; for 48h; | 93% |
With sodium hydroxide In methanol; water at 80℃; for 10h; Temperature; Large scale; | 91.06% |
Stage #1: 2-Cyano-4'-methylbiphenyl With sodium hydroxide In ethylene glycol at 170℃; for 8h; Stage #2: With hydrogenchloride In water; toluene | 90.4% |
2-Cyano-4'-methylbiphenyl
4-methyl-2'-thiocarboxamido-1,1'-biphenyl
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 92% |
Stage #1: 2-Cyano-4'-methylbiphenyl With magnesium(II) chloride hexahydrate; sodium monohydrogensulphide hydrate In water; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With hydrogenchloride In water for 0.333333h; | 92.1% |
4'-Methyl-2-cyanobiphenyl (CAS NO.114772-53-1) is used for pharmaceutical intermediates .
4'-Methyl-2-cyanobiphenyl , its cas register number is 114772-53-1. It also can be called 4'-Methylbiphenyl-2-carbonitrile ; 2-Cyano-4'-methylbiphenyl .It is a white crystalline powder.It insoluble in water.
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