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114772-53-1

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114772-53-1 Usage

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 114772-53-1 differently. You can refer to the following data:
1. 4'-Methylbiphenyl-2-carbonitrile is an intermediate in the synthesis of glycogen synthase kinase-3 inhibitors with a selective sting for glycogen synthase kinase 3α.
2. 4''-Methylbiphenyl-2-carbonitrile is an intermediate in the synthesis of glycogen synthase kinase-3 inhibitors with a selective sting for glycogen synthase kinase 3α.

Check Digit Verification of cas no

The CAS Registry Mumber 114772-53-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,4,7,7 and 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 114772-53:
(8*1)+(7*1)+(6*4)+(5*7)+(4*7)+(3*2)+(2*5)+(1*3)=121
121 % 10 = 1
So 114772-53-1 is a valid CAS Registry Number.

114772-53-1 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (B21273)  2-Cyano-4'-methylbiphenyl, 98+%   

  • 114772-53-1

  • 5g

  • 368.0CNY

  • Detail
  • Alfa Aesar

  • (B21273)  2-Cyano-4'-methylbiphenyl, 98+%   

  • 114772-53-1

  • 25g

  • 1221.0CNY

  • Detail
  • Alfa Aesar

  • (B21273)  2-Cyano-4'-methylbiphenyl, 98+%   

  • 114772-53-1

  • 100g

  • 3350.0CNY

  • Detail
  • Aldrich

  • (459569)  4′-Methyl-2-biphenylcarbonitrile  98%

  • 114772-53-1

  • 459569-25G

  • 2,529.54CNY

  • Detail

114772-53-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4'-Methyl-2-cyanobiphenyl

1.2 Other means of identification

Product number -
Other names 2'-cyano-4-methyl-1,1'-biphenyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:114772-53-1 SDS

114772-53-1Synthetic route

2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
2042-37-7

o-cyanobromobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
873-32-5

2-Chlorobenzonitrile

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
873-32-5

2-Chlorobenzonitrile

4'-methyl-2-acetyl-1,1'-biphenyl
16927-79-0

4'-methyl-2-acetyl-1,1'-biphenyl

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With cesium fluoride; Pd(dba)2 In 1,4-dioxane98%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

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

di(p-tolyl)borinic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
2042-37-7

o-cyanobromobenzene

potassium (4-methylphenyl)trifluoroborate

potassium (4-methylphenyl)trifluoroborate

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
84392-32-5

4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
2042-37-7

o-cyanobromobenzene

4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With 1,2-dimethoxyethane; Cl4Li2Pd; 1,3-bis-(diphenylphosphino)propane95%
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 diacetate94%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With palladium diacetate; XPhos In toluene at 120℃; for 40h; Inert atmosphere; Sealed tube;95%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

p-tolylzinc(II) chloride
90252-89-4

p-tolylzinc(II) chloride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

para-chlorotoluene
106-43-4

para-chlorotoluene

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
PdCl2/dppp

PdCl2/dppp

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; 1,2-dimethoxyethane93%
p-toluidine
106-49-0

p-toluidine

benzonitrile
100-47-0

benzonitrile

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
4'-methylbiphenyl-2-carboxime

4'-methylbiphenyl-2-carboxime

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With phosphorus pentoxide In tetrahydrofuran at 20℃; for 1h;92%
4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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;
2-cyanophenyl 1H-imidazole-1-sulfonate

2-cyanophenyl 1H-imidazole-1-sulfonate

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With C26H16Cl6N2O2Pd2; tetrabutylammomium bromide; potassium hydroxide In methanol; water at 110℃; for 0.333333h; Suzuki coupling; Microwave irradiation;92%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

tributyl(p-tolyl)stannane
31614-66-1

tributyl(p-tolyl)stannane

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide Inert atmosphere;92%
4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

4-methyl-8-(4-methylphenyl)-2,6-dioxotetrahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide

2-cyanobenzene-1-sulfonyl fluoride
395-46-0

2-cyanobenzene-1-sulfonyl fluoride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; diisopropylamine In ethanol; water at 25℃; for 4h;92%
o-(p-tolyl)benzaldoxime

o-(p-tolyl)benzaldoxime

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With formic acid91%
2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
873-32-5

2-Chlorobenzonitrile

4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
824-79-3

sodium 4-methylbenzenesulfinate

2-<(trifluoromethanesulfonyl)oxy>benzonitrile
138313-23-2

2-<(trifluoromethanesulfonyl)oxy>benzonitrile

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With palladium diacetate; XPhos In toluene at 120℃; for 24h; Sealed tube; Inert atmosphere;90%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
4-tolyl iodide
624-31-7

4-tolyl iodide

2-Cyanophenylboronic acid
138642-62-3

2-Cyanophenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With Ti0.97Pd0.03O1.97; potassium carbonate In water at 100℃; for 6h; Suzuki-Miyaura Coupling;89%
NiCl2 (Ph3 P)2

NiCl2 (Ph3 P)2

ethyl acetate n-hexane

ethyl acetate n-hexane

para-bromotoluene
106-38-7

para-bromotoluene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane88%
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane88%
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane88%
NiCl2 (Ph3 P)2

NiCl2 (Ph3 P)2

para-bromotoluene
106-38-7

para-bromotoluene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With hydrogenchloride; tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran; pentane88%
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
2042-37-7

o-cyanobromobenzene

4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

palladium dichloride

palladium dichloride

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; water; toluene88%
para-bromotoluene
106-38-7

para-bromotoluene

2-(cyano)halobenzene

2-(cyano)halobenzene

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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%
Pd2 (dba)3

Pd2 (dba)3

2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With cesium fluoride In 1,4-dioxane87%
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl
120568-11-8

2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl

Conditions
ConditionsYield
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
114772-53-1

2-Cyano-4'-methylbiphenyl

methyl 2-diazo-2-(fluorosulfonyl)acetate

methyl 2-diazo-2-(fluorosulfonyl)acetate

5-methoxy-2-(4'-methyl-[1,1'-biphenyl]-2-yl)oxazole-4-sulfonyl fluoride

5-methoxy-2-(4'-methyl-[1,1'-biphenyl]-2-yl)oxazole-4-sulfonyl fluoride

Conditions
ConditionsYield
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
114772-53-1

2-Cyano-4'-methylbiphenyl

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane96%
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
114772-53-1

2-Cyano-4'-methylbiphenyl

5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole
120568-11-8

5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole

Conditions
ConditionsYield
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
114772-53-1

2-Cyano-4'-methylbiphenyl

4-Methylbiphenyl-2'-carboxamidoxime
147403-93-8

4-Methylbiphenyl-2'-carboxamidoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol; dimethyl sulfoxide96%
With hydroxylamine hydrochloride; triethylamine In dimethyl sulfoxide at 80 - 85℃; for 24h; Reagent/catalyst; Solvent;89.6%
aqueous hydrochloric acid(pH 1)

aqueous hydrochloric acid(pH 1)

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl
120568-11-8

2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl

Conditions
ConditionsYield
Zinc chloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide94%
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

o-(p-tolyl)-benzylamine hydrochloride
1536169-09-1

o-(p-tolyl)-benzylamine hydrochloride

Conditions
ConditionsYield
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
114772-53-1

2-Cyano-4'-methylbiphenyl

o-tolylbenzoic acid
7148-03-0

o-tolylbenzoic acid

Conditions
ConditionsYield
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
114772-53-1

2-Cyano-4'-methylbiphenyl

4-methyl-2'-thiocarboxamido-1,1'-biphenyl
162356-74-3

4-methyl-2'-thiocarboxamido-1,1'-biphenyl

Conditions
ConditionsYield
With hydrogenchloride In methanol92%
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%

114772-53-1Relevant articles and documents

Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides

Walla, Peter,Kappe, C. Oliver

, p. 564 - 565 (2004)

Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.

4′-Methylbiphenyl-2-carbonitrile synthesis by continuous flow Suzuki-Miyaura reaction

Estrada, Gizelda O.D.,Flores, Marcella C.,Da Silva, Joaquim F.M.,De Souza, Rodrigo O.M.A.,E Miranda, Leandro S.M.

, p. 4166 - 4168 (2012)

In the present work we report a high selective synthesis of the bicyclic core present in an important angiotensin II inhibitor family of drugs (Sartans) under continuous flow conditions. The key step in our approach was a Suzuki-Miyaura coupling using for the first time the recently described 4-toluylboronic acid MIDA ester.

Maghemite decorated with ultra-small palladium nanoparticles (γ-Fe2O3-Pd): Applications in the Heck-Mizoroki olefination, Suzuki reaction and allylic oxidation of alkenes

Rathi, Anuj K.,Gawande, Manoj B.,Pechousek, Jiri,Tucek, Jiri,Aparicio, Claudia,Petr, Martin,Tomanec, Ondrej,Krikavova, Radka,Travnicek, Zdenek,Varma, Rajender S.,Zboril, Radek

, p. 2363 - 2373 (2016)

A nanocatalyst comprising ultra-small Pd/PdO nanoparticles (57Fe M?ssbauer spectroscopy. The cost-effective catalyst could be easily separated from the reaction mixture by using an external magnet and reused four times without any loss of activity; chemical stability and recyclability aspects of the catalyst were investigated.

Highly efficient palladium catalysts supported on nitrogen contained polymers for Suzuki-Miyaura reaction

Geng, Longfei,Li, Yan,Qi, Zhengliang,Fan, Haipeng,Zhou, Zhicheng,Chen, Rizhi,Wang, Yong,Huang, Jun

, p. 24 - 28 (2016)

Through Pd catalyzed C-N coupling reaction, Pd nanoparticles and diadamantylphosphine ligand were immobilized in situ into the formed N contained polymers as heterogeneous Pd catalysts for Suzuki-Miyaura reaction. The Pd@NPad2-1.0 catalyst was found to be highly efficient and only 4 ppm of Pd (Pd@NPad2-1.0) was required for the coupling of aryl bromides with phenylboronic acid, and the corresponding products were obtained in good to excellent yields with high TON and TOF as 250,000 and 41,666 h- 1 respectively. Moreover, the coupling of various aryl chlorides with phenylboronic acids gave the corresponding products in high yields also. And the Pd@NPad2-1.0 catalyst is reusable at least 5 times with only slight deactivation.

Benzyloxycalix[8]arene: A new valuable support for NHC palladium complexes in C-C Suzuki-Miyaura couplings

Abdellah, Ibrahim,Kasongo, Pauline,Labattut, Axel,Guillot, Régis,Schulz, Emmanuelle,Martini, Cyril,Huc, Vincent

, p. 13843 - 13848 (2018)

Benzyloxycalix[8]arene supported catalysts bearing N-heterocyclic carbene palladium complexes on each subunit were readily synthesized. Intermediates and catalysts were fully characterized, allowing for a fine control of their structure. X-ray diffraction analysis confirmed the formation of a calix[8]arene bearing eight well-defined NHC palladium complexes. The macrocyclic structure of calix[8]arenes allowed for a scalable and chromatography-free catalyst synthesis under homogeneous conditions, while the catalytic reaction proceeded under heterogeneous conditions, just by changing the nature of the solvent. Indeed, when used as a suspension in ethanol, a high TON and TOF were obtained through a large panel of functionalized brominated substrates in C-C Suzuki-Miyaura couplings, with low metal contamination after simple filtration.

Ligand-Promoted Direct C-H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism

Kim, Jaewoon,Hong, Soon Hyeok

, p. 3336 - 3343 (2017)

A highly efficient catalyst for the direct C-H arylation of simple arenes was developed on the basis of a palladium-diimine complex. The developed catalyst exhibited the highest turnover number reported to date for the direct arylation of benzene due to increased stability provided by the diimine ligand. The reaction was also performed using only 2-3 equiv of simple arenes. Mechanistic studies in combination with kinetic measurements, isotope effect experiments, synthesis of possible intermediates, and stoichiometric reactions suggested that this reaction follows a cooperative bimetallic mechanism.

Palladium-catalyzed desulfitative cross-coupling of sodium arylsulfinates with aryl bromides and chlorides: An alternative convenient synthesis of biaryls

Zhou, Chao,Li, Yaming,Lu, Yang,Zhang, Rong,Jin, Kun,Fu, Xinmei,Duan, Chunying

, p. 1269 - 1273 (2013)

An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. Copyright

Development of unimolecular tetrakis(piperidin-4-ol) as a ligand for Suzuki-Miyaura cross-coupling reactions: Synthesis of incrustoporin and preclamol

Nallasivam, Jothi L.,Fernandes, Rodney A.

, p. 3558 - 3567 (2015)

Abstract A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol. A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono-, bis-, tris-, and tetrakis-unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields.

A cross-coupling synthesis of functionalised biaryls using Knochel-type organozinc reagents and a pyridine enhanced palladium catalyst

Wang, Min,Liu, Fang,Zeng, Meng-Tian,Xu, Wan,Liu, Min,Dong, Zhi-Bing

, p. 382 - 384 (2016)

A variety of functionalised biaryls were synthesised on the 20-30 mmol scale by using Knochel type organozinc reagents (organozinc reagents prepared from aryl halides, Zn powder and LiCl) catalysed by PEPPSI (a pyridine enhanced palladium catalyst). The protocol enabled the Negishi reactions to proceed in a smooth, rapid and mild way to give the corresponding products in excellent yields (80 ~ 96%). Sensitive functional groups, such as CN and COOEt groups, were tolerated in the coupling reaction.

Cu-Catalyzed Denitrogenative Ring-Opening of 3-Aminoindazoles for the Synthesis of Aromatic Nitrile-Containing (Hetero)Arenes

Zhou, Yao,Deng, Shuilin,Mai, Shaoyu,Song, Qiuling

, p. 6161 - 6165 (2018)

An unprecedented Cu-catalyzed oxidative cleavage of two C-N bonds of 3-aminoindazoles is reported herein, which represents the first example for denitrogenative ring-opening of 3-aminoindazoles. This novel reactivity of 3-aminoindazoles enables the produc

Investigations into the Suzuki-Miyaura coupling aiming at multikilogram synthesis of E2040 using (o-cyanophenyl)boronic esters

Urawa, Yoshio,Naka, Hiroyuki,Miyazawa, Mamoru,Souda, Shigeru,Ogura, Katsuyuki

, p. 269 - 278 (2002)

The Suzuki-Miyaura cross-coupling reaction between 1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine ((R)-1b) and thermally unstable (0-cyanophenyl)boronic ester 6b in the presence of dichlorobis(triphenylphosphine)palladium and potassium phosph

Synthetic applications of oxime-derived palladacycles as versatile catalysts in cross-coupling reactions

Alonso, Diego A.,Botella, Luis,Najera,Pacheco, Ma. Carmen

, p. 1713 - 1718 (2004)

Palladacycles 1 and 2, derived from 4,4′-dichlorobenzophenone and 4-hydroxyacetophenone oximes, respectively, are very efficient and versatile pre-catalysts for a wide range of carbon-carbon bond coupling reactions such as, Mizoroki-Heck, Suzuki-Miyaura, Stille, Ullmann-type, Sonogashira, sila-Sonogashira, Glaser and acylation of alkynes under very low loading conditions in air and either in organic or aqueous solvents, employing reagent-grade chemicals. High yielding, general, and practical procedures for the palladium-catalyzed Mizoroki-Heck, Suzuki-Miyaura, Ullmann-type, Sonogashira and sila-Sonogashira reactions are described.

Palladium Supported on Graphitic Carbon Nitride: An Efficient and Recyclable Heterogeneous Catalyst for Reduction of Nitroarenes and Suzuki Coupling Reaction

Zhao, Yukai,Tang, Ruiren,Huang, Rong

, p. 1961 - 1971 (2015)

In this study, a novel platelet-like nanocatalyst, Pd/g-C3N4 with easily approachable active sites, was developed. The mesoporous graphitic carbon nitride (g-C3N4) is a layered structure connected by planar amino groups, which can work as stabilizer and active support for noble metal nanoparticles. The palladium nanoparticles with an average particle size of 3.25 nm were evenly dispersed on the surface of g-C3N4 without aggregation. Detailed charaterizations reveal that there is no covalent-bond interaction between g-C3N4 and Pd NPs. The Pd/g-C3N4 catalyst showed excellent catalytic activity in the reduction of nitroarenes by NaBH4, and Suzuki coupling reaction of aryl halides with arylboronic acids under mild conditions. The reduction of 4-nitrophenol has a pseudo-first-order rate constant of 7.29 × 10-3 s-1, and an activity parameter of 1.37 s-1 mM-1, which is higher than those reported in the literature. Furthermore, the Suzuki coupling reactions processed smoothly with 97.0 % isolate yield in less than 30 min in water with PEG600 as the additive. The catalyst could be recycled for five times without significant loss of catalytic activity, which confirmed the good stability of the catalyst. Graphical Abstract: [Figure not available: see fulltext.]

Cathodic aromatic C,C cross-coupling reaction via single electron transfer pathway

Qu, Yang,Tateno, Hiroyuki,Matsumura, Yoshimasa,Kashiwagi, Tsuneo,Atobe, Mahito

, (2017)

We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.

Trinuclear copper(I) complex of 1,3-bis(2-pyridinylmethyl)imidazolylidene as a carbene-transfer reagent for the preparation of catalytically active nickel(II) and palladium(II) complexes

Chen, Chao,Qiu, Huayu,Chen, Wanzhi

, p. 4166 - 4172 (2012)

Reactions of 1,3-bis(pyridin-2-ylmethyl)-1H-imidazol-3-ium hexafluorophosphate, ([HL1](PF6), L1 = 1,3-bis(pyridin-2-ylmethyl) imidazolylidene) and 1,3-bis(pyridin-2-ylmethyl)-1H-benzimidazol-3-ium hexafluorophosphate ([HL2](PF6), L2 = 1,3-bis(pyridin-2-ylmethyl) benzoimidazolylidene) with cuprous oxide in acetonitrile readily yielded trinuclear complexes [Cu3(L1)3(PF6) 3] (1) and [Cu3(L2)3(PF6) 3] (2). Treatment of 1 with Ni(PPh3)2Cl 2 and Pd(cod)Cl2 gave [Ni(L1)Cl](PF6) (3) and [Pd(L1)Cl](PF6) (4), respectively, due to transmetalation. [Ni(L1)2](PF6)2 (5) was obtained from the reaction of [Cu3(L1)3(PF6)3] and Raney nickel in acetonitrile. All these complexes have been fully characterized. Both 1 and 2 consist of a triangular Cu3 core with each Cu-Cu bond capped by an imidazolylidene group. Each imidazolylidene acts as a bridging ligand in a μ2 mode and is bonded equally to two Cu(I) ions. The pincer nickel and palladium complexes are square-planar and contain a tridentate NCN ligand. Complexes 3 and 4 are efficient catalyst precursors for Kumada-Corriu and Suzuki-Miyaura coupling reactions of aryl halides with organometallic reagents.

Molecular sieves-supported palladium(II) catalyst: Suzuki coupling of?chloroarenes and an easy access to useful intermediates for the synthesis of?irbesartan, losartan and boscalid

Dey, Raju,Sreedhar, Bojja,Ranu, Brindaban C.

, p. 2301 - 2305 (2010)

Palladium(II) chloride supported on 4 ? molecular sieves efficiently catalyzes the Suzuki coupling reactions of chlorobenzenes in presence of tetrabutylammonium bromide without any ligand. The useful intermediates for the synthesis of bioactive compounds such as irbesartan, and losartan have been prepared in one step following this reaction. The preparation of this catalyst is very simple. The FE-SEM image shows a cube shape ordered structure. The catalyst does not exhibit any nanoparticles as indicated by TEM. EDS and XPS demonstrate anchoring of Pd on molecular sieves in +2 oxidation state. This heterogeneous catalyst is stable, non-air sensitive and recyclable.

Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism

Antonacci, Giuseppe,Ahlburg, Andreas,Fristrup, Peter,Norrby, Per-Ola,Madsen, Robert

, p. 4758 - 4764 (2017)

The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an SRN1 mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide.

New Practical Syntheses of 4′-Methylbiphenyl-2-carbonitrile and -2-carbaldehyde

Goubet, Dominique,Meric, Pascal,Dormoy, Jean-Robert,Moreau, Patrice

, p. 4516 - 4518 (1999)

-

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

Sharma, Brijesh M.,Nikam, Arun V.,Lahore, Santosh,Ahn, Gwang-Noh,Kim, Dong-Pyo

supporting information, (2022/02/25)

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

Synthesis, characterization and biological evaluation of benzimidazole and benzindazole derivatives as anti-hypertensive agents

Silky, Sethy,Mandal, Sudip Kumar,Ewies, Ewies Fawzy,Neerupma, Dhiman,Arun, Garg

, p. 3659 - 3664 (2021/07/10)

A substituted benzimidazole and benzindazole derivatives had been synthesized having antihypertensive activity through antagonizing the angiotensin II (Ang II) receptors. The in vivo antihypertensive activity of the compounds was done with acute renal hypertension model. Two compounds TG 1 and TG 3 were found to have antihypertensive activity comparable to Telmisartan which is a prototype for Angiotensin II receptor antagonists class of drugs.In an antihypertensive study the compounds TG 1, TG 2 and TG 3 had systolic blood pressures of 147.2 mm/Hg, 168.2 mm/Hg, and 126.3 mm/Hg, respectively. This systolic blood pressure was lower than the disease control vehicle-treated rodents, which had a systolic blood pressure of 167.2 mm/Hg. The diastolic blood pressure was 119.7 mm/Hg, 124.7 mm/Hg and 88.83 mm/Hg, respectively and that of the disease control vehicle-treated rodents was 122.3 mm/Hg. TG 3 had comparable decrease in the MABP to Telmisartan. These encouraging results make compound TG 3 effective anti-hypertensive drug candidate and worthy of further investigation.

A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents

He, Xiao-Yun

, p. 823 - 832 (2021/07/19)

Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].

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