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114772-54-2

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114772-54-2 Usage

Chemical Properties

4-Bromomethyl-2-cyanobiphenyl is Cream powder

Uses

4-Bromomethyl-2-cyanobiphenyl used in protein-binding studies of quinoxaline angiotensin II receptor antagonists.

Check Digit Verification of cas no

The CAS Registry Mumber 114772-54-2 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 4 respectively.
Calculate Digit Verification of CAS Registry Number 114772-54:
(8*1)+(7*1)+(6*4)+(5*7)+(4*7)+(3*2)+(2*5)+(1*4)=122
122 % 10 = 2
So 114772-54-2 is a valid CAS Registry Number.

114772-54-2 Well-known Company Product Price

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  • Alfa Aesar

  • (H55394)  4'-(Bromomethyl)biphenyl-2-carbonitrile, 98%   

  • 114772-54-2

  • 1g

  • 102.0CNY

  • Detail
  • Alfa Aesar

  • (H55394)  4'-(Bromomethyl)biphenyl-2-carbonitrile, 98%   

  • 114772-54-2

  • 5g

  • 364.0CNY

  • Detail
  • Alfa Aesar

  • (H55394)  4'-(Bromomethyl)biphenyl-2-carbonitrile, 98%   

  • 114772-54-2

  • 25g

  • 1820.0CNY

  • Detail
  • Aldrich

  • (535494)  4′-Bromomethyl-2-biphenylcarbonitrile  97%

  • 114772-54-2

  • 535494-5G

  • 895.05CNY

  • Detail
  • Aldrich

  • (535494)  4′-Bromomethyl-2-biphenylcarbonitrile  97%

  • 114772-54-2

  • 535494-25G

  • 2,923.83CNY

  • Detail

114772-54-2SDS

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-Bromomethyl-2-cyanobiphenyl

1.2 Other means of identification

Product number -
Other names 4`-Bromomethyl-2-cyanobiphenyl

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:114772-54-2 SDS

114772-54-2Synthetic route

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
64113-85-5

2-cyano-4-methylbiphenyl

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

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

Conditions
ConditionsYield
With 5,5-dibromohydantoin In dichloromethane at 50℃; for 0.5h; Temperature; Reagent/catalyst; Irradiation;94%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 100℃; for 2h;
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2,2'-azobis-(4-methoxy-2,4-dimethylvaleronitrile)

2,2'-azobis-(4-methoxy-2,4-dimethylvaleronitrile)

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

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

Conditions
ConditionsYield
With bromine In water89.4%
With N-Bromosuccinimide In water79.6%
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

A

2-(4,4-dibromomethylphenyl)benzonitrile
209911-63-7

2-(4,4-dibromomethylphenyl)benzonitrile

B

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

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

Conditions
ConditionsYield
With N-Bromosuccinimide; Azo-bis(2,4-dimethyl-valeronitril) In dichloromethane at 45 - 50℃; for 2 - 5h; Industry scale;A n/a
B 82%
With sodium bromate; hydrogen bromide In dichloromethane; water at 0 - 20℃; UV-irradiation;A 10%
B 80%
With sodium bromate; azobis(2-cyanobutane); bromine In water; chlorobenzene at 70 - 80℃; for 6h;A n/a
B 69%
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

2,2'-azobis (2,4-dimethyl valeronitrile)
4419-11-8, 108346-39-0, 108346-40-3

2,2'-azobis (2,4-dimethyl valeronitrile)

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

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

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane; water80.5%
2,2'-azobis(2-methylbutyronitrile)

2,2'-azobis(2-methylbutyronitrile)

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

2-Cyano-4'-methylbiphenyl

chlorobenzene
108-90-7

chlorobenzene

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

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

Conditions
ConditionsYield
With bromine75%
2-cyanobenzoic acid
3839-22-3

2-cyanobenzoic acid

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C
2: 45 percent / N-bromosuccinimide; azobis(isobutyronitrile) / CCl4; cyclohexane / 18 h / 75 °C
View Scheme
ammonium 2-(aminocarbonyl)benzoate
131-63-5

ammonium 2-(aminocarbonyl)benzoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72 percent / acetic anhydride; pyridine
2: 71 percent / copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C
3: 45 percent / N-bromosuccinimide; azobis(isobutyronitrile) / CCl4; cyclohexane / 18 h / 75 °C
View Scheme
2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline
57598-33-1

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: magnesium / tetrahydrofuran
2: hydrogenchloride
3: thionyl chloride / water; toluene
4: dibenzoyl peroxide
View Scheme
N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide
74201-13-1

N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / 1 h / 25 °C
2: tetrahydrofuran / 2 h / 20 °C
3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
View Scheme
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

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride
2: thionyl chloride / water; toluene
3: dibenzoyl peroxide
View Scheme
2-Methoxybenzoic acid
579-75-9

2-Methoxybenzoic acid

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 95 percent / thionyl chloride / 18 h / 20 °C
2: CH2Cl2 / 2 h / 20 °C
3: thionyl chloride / 1 h / 25 °C
4: tetrahydrofuran / 2 h / 20 °C
5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
6: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
View Scheme
2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: CH2Cl2 / 2 h / 20 °C
2: thionyl chloride / 1 h / 25 °C
3: tetrahydrofuran / 2 h / 20 °C
4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
View Scheme
chlorobenzene
108-90-7

chlorobenzene

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

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

Conditions
ConditionsYield
In water
sodium bromate

sodium bromate

2,2'-azobis(2-methylbutyronitrile)

2,2'-azobis(2-methylbutyronitrile)

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
In water; chlorobenzene
In water; chlorobenzene
2,2'-azobis(2,4-dimethylvaleronitrile)

2,2'-azobis(2,4-dimethylvaleronitrile)

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

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

tetrachloromethane
56-23-5

tetrachloromethane

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

2-Cyano-4'-methylbiphenyl

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

4'-bromornethyl-2-cyanobiphenyl

4'-bromornethyl-2-cyanobiphenyl

B

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

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

azobisisobutyronitrile
34241-39-9

azobisisobutyronitrile

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 In water; chlorobenzene
With N-Bromosuccinimide In water; chlorobenzene
With N-Bromosuccinimide In tetrachloromethane
With N-Bromosuccinimide In tetrachloromethane
With N-Bromosuccinimide In tetrachloromethane
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

Losartan ›DUP[753]

Losartan ›DUP[753]

B

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

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

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane
2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

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

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

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane
With N-Bromosuccinimide In tetrachloromethane
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; toluene / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 40 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / Inert atmosphere
2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane
View Scheme
Multi-step reaction with 2 steps
1.1: palladium dichloride / methanol; toluene / 0.17 h / 20 °C / Inert atmosphere
1.2: 12 h / 110 °C / Inert atmosphere
2.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chlorobenzene / 6 h / 70 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / toluene / 6 h / 110 °C / Inert atmosphere
2: sodium bromate; sodium metabisulfite / ethyl acetate; water / 5 h / 0 - 25 °C
View Scheme
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; toluene / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 40 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: palladium dichloride / methanol; toluene / 0.17 h / 20 °C / Inert atmosphere
1.2: 12 h / 110 °C / Inert atmosphere
2.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chlorobenzene / 6 h / 70 °C / Inert atmosphere
View Scheme
benzaldehyde N,N-dimethylhydrazone
1075-70-3

benzaldehyde N,N-dimethylhydrazone

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 4-(dimethylamino)picolinaldehyde N,N-dibenzylhydrazone; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium phosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
3: magnesium bis(monoperoxyphthalate)hexahydrate / methanol / 0 h / 20 °C
4: sodium metabisulfite; sodium bromate / water; ethyl acetate / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 4-(dimethylamino)picolinaldehyde N,N-dibenzylhydrazone; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere
2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium phosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
3: magnesium bis(monoperoxyphthalate)hexahydrate / methanol / 0 h / 20 °C
4: sodium metabisulfite; sodium bromate / water; ethyl acetate / 20 °C
View Scheme
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone
1360607-13-1

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium phosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
2: magnesium bis(monoperoxyphthalate)hexahydrate / methanol / 0 h / 20 °C
3: sodium metabisulfite; sodium bromate / water; ethyl acetate / 20 °C
View Scheme
4′-methyl-[1,1′-biphenyl]-2-carbaldehyde N,N-dimethylhydrazone
1404116-53-5

4′-methyl-[1,1′-biphenyl]-2-carbaldehyde N,N-dimethylhydrazone

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium bis(monoperoxyphthalate)hexahydrate / methanol / 0 h / 20 °C
2: sodium metabisulfite; sodium bromate / water; ethyl acetate / 20 °C
View Scheme
tributyl(p-tolyl)stannane
31614-66-1

tributyl(p-tolyl)stannane

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / Inert atmosphere
2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane
View Scheme
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: manganese(ll) chloride; chloro-trimethyl-silane / tetrahydrofuran / -5 - 0 °C / Inert atmosphere; Green chemistry
1.2: 9 h / -5 - 25 °C / Inert atmosphere; Green chemistry
2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 80 °C / Green chemistry
View Scheme
4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: manganese(ll) chloride; chloro-trimethyl-silane / tetrahydrofuran / -5 - 0 °C / Inert atmosphere; Green chemistry
1.2: 9 h / -5 - 25 °C / Inert atmosphere; Green chemistry
2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 80 °C / Green chemistry
View Scheme
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

Methyl 3-nitro-4-valerylaminobenzoate
127007-35-6

Methyl 3-nitro-4-valerylaminobenzoate

4-[(2'-Cyano-biphenyl-4-ylmethyl)-pentanoyl-amino]-3-nitro-benzoic acid methyl ester
136285-45-5

4-[(2'-Cyano-biphenyl-4-ylmethyl)-pentanoyl-amino]-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 15h; Ambient temperature;100%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

ethyl butyroyl acetate
3249-68-1

ethyl butyroyl acetate

ethyl 2-<(2'-cyanobiphenyl-4-yl)methyl>-3-oxohexanoate
137860-26-5

ethyl 2-<(2'-cyanobiphenyl-4-yl)methyl>-3-oxohexanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;98%
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating; Yield given;
L-valine benzyl ester p-toluenesulfonate salt
16652-76-9

L-valine benzyl ester p-toluenesulfonate salt

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

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

(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride
137864-24-5

(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride

Conditions
ConditionsYield
Stage #1: L-valine benzyl ester p-toluenesulfonate salt With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 20℃; pH=< 8.5 - 9; Large scale;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 3.41667h; Large scale;
Stage #3: With hydrogenchloride In 5,5-dimethyl-1,3-cyclohexadiene; water at 72℃; for 2h; Dean-Stark; Large scale;
98%
Stage #1: L-valine benzyl ester p-toluenesulfonate salt; 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile With tetrabutylammomium bromide; potassium carbonate; potassium iodide In water; toluene at 50 - 55℃; for 25h;
Stage #2: With hydrogenchloride In water; toluene pH=1 - 2; Product distribution / selectivity;
90%
Stage #1: L-valine benzyl ester p-toluenesulfonate salt; 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile With tetrabutylammomium bromide; potassium carbonate; potassium iodide In water; toluene
Stage #2: With hydrogenchloride In water; toluene pH=1 - 2; Product distribution / selectivity;
90%
N-phenylpentanamide
10264-18-3

N-phenylpentanamide

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

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

N-((2′-cyano[1,1′-biphenyl]-4-yl)methyl)-N-phenylpentanamide

N-((2′-cyano[1,1′-biphenyl]-4-yl)methyl)-N-phenylpentanamide

Conditions
ConditionsYield
Stage #1: N-phenylpentanamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
98%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine
143096-18-8

N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

Conditions
ConditionsYield
96%
methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate hydrochloride
1206680-19-4

methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate hydrochloride

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

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

2-cyano-4'-[2
1098100-86-7

2-cyano-4'-[2"-n-propyl-4"-methyl-6"-methylcarboxylate-benzimidazole-1"-ylmethyl]biphenyl

Conditions
ConditionsYield
Stage #1: methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate hydrochloride With sodium carbonate; sodium iodide In acetone
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In acetone for 15h; Product distribution / selectivity; Reflux;
95%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

4'-(benzothiazol-2-ylsulfanylmethyl)-biphenyl-2-carbonitrile
721970-96-3

4'-(benzothiazol-2-ylsulfanylmethyl)-biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 20℃; for 1.33333h;94.7%
2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-thione
1429045-74-8

2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-thione

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

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

C29H20FN3S2
1429045-99-7

C29H20FN3S2

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;94%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-[(2'-cyanobiphenyl-4-yl)methoxy]benzoate

methyl 4-[(2'-cyanobiphenyl-4-yl)methoxy]benzoate

Conditions
ConditionsYield
With potassium carbonate In butanone at 78 - 80℃; for 2h;93.5%
2-butyl-4-(4-fluorophenyl)-1H-imidazole-5-carbaldehyde
1313233-70-3

2-butyl-4-(4-fluorophenyl)-1H-imidazole-5-carbaldehyde

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

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

4'-[{2-butyl-4-(4-fluorophenyl)-5-formyl-1H-imidazol-1-yl}methyl]biphenyl-2-carbonitrile
1313233-71-4

4'-[{2-butyl-4-(4-fluorophenyl)-5-formyl-1H-imidazol-1-yl}methyl]biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;93.2%
Ethyl 3-oxoheptanoate
7737-62-4

Ethyl 3-oxoheptanoate

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

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

2-(2'-Cyano-biphenyl-4-ylmethyl)-3-oxo-heptanoic acid ethyl ester
137860-02-7

2-(2'-Cyano-biphenyl-4-ylmethyl)-3-oxo-heptanoic acid ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;93%
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating; Yield given;
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

(6-Butyl-2-oxo-1,2-dihydro-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester
147876-57-1

(6-Butyl-2-oxo-1,2-dihydro-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-1,2-dihydro-2-oxo-3-tert-butoxycarbonylaminomethyl pyridine
147876-52-6

6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-1,2-dihydro-2-oxo-3-tert-butoxycarbonylaminomethyl pyridine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 72h; Heating;92%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

dimethyl amine
124-40-3

dimethyl amine

4'-((dimethylamino)methyl)-[1,1'-biphenyl]-2-carbonitrile
1000930-96-0

4'-((dimethylamino)methyl)-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
In diethyl ether; water at 20℃;92%
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione
666816-98-4

8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

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

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

4'-((8-bromo-7-(but-2-ynyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl)biphenyl-2-carbonitrile

4'-((8-bromo-7-(but-2-ynyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 6h;92%
benzoimidazole
51-17-2

benzoimidazole

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

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

4′-((1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carbonitrile
136285-25-1

4′-((1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
Stage #1: benzoimidazole With potassium hydroxide In dimethyl sulfoxide at 100℃; for 2h;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In dimethyl sulfoxide for 12h;
92%
5-methyl-3-oxo-hexanoic acid ethyl ester
34036-16-3

5-methyl-3-oxo-hexanoic acid ethyl ester

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

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

2-(2'-Cyano-biphenyl-4-ylmethyl)-5-methyl-3-oxo-hexanoic acid ethyl ester
137860-48-1

2-(2'-Cyano-biphenyl-4-ylmethyl)-5-methyl-3-oxo-hexanoic acid ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;91%
2-propyl-1H-benzimidazole
5465-29-2

2-propyl-1H-benzimidazole

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

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

4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile
136285-23-9

4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
Stage #1: 2-propyl-1H-benzimidazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In N,N-dimethyl-formamide at 0 - 20℃;
91%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Cooling with ice;70%
Stage #1: 2-propyl-1H-benzimidazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
quinazoline-4(3H)-thione
3337-86-8

quinazoline-4(3H)-thione

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

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

C22H15N3S
1429045-94-2

C22H15N3S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;91%
1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

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

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

hydrobromide 4'-(3,4-dihydropyrimido[1,2-a]benzimidazole-10(2H)-ylmethyl) biphenyl-2-carbonitrile

hydrobromide 4'-(3,4-dihydropyrimido[1,2-a]benzimidazole-10(2H)-ylmethyl) biphenyl-2-carbonitrile

Conditions
ConditionsYield
In nitromethane for 7.5h; Heating;91%
7-amino-4-(azidomethyl)-2H-chromen-2-one
1186293-68-4

7-amino-4-(azidomethyl)-2H-chromen-2-one

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

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

C24H17N5O2

C24H17N5O2

Conditions
ConditionsYield
With sodium carbonate In acetone for 6h; Reflux;90.5%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride

2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile
138401-24-8

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 0.0208333h; microwave irradiation;90%
Stage #1: 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride With potassium carbonate; tetrabutylammomium bromide In water at 25 - 30℃; for 2h; Inert atmosphere;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In water at 55 - 60℃; Product distribution / selectivity;
84.2%
With tetrabutylammomium bromide; sodium hydroxide In Isopropyl acetate at 0 - 30℃; for 12h; Solvent;39%
4-amino-phenol
123-30-8

4-amino-phenol

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

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

4'-((4-hydroxyphenylamino)methyl)biphenyl-2-carbonitrile

4'-((4-hydroxyphenylamino)methyl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Reflux;90%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

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

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

4'-((4-(trifluoromethyl)phenylamino)methyl)biphenyl-2-carbonitrile

4'-((4-(trifluoromethyl)phenylamino)methyl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Reflux;90%
5-chloro-1,7’-dimethyl-2’-propyl-1H,3’H-2,5’-bibenzo[d]imidazole

5-chloro-1,7’-dimethyl-2’-propyl-1H,3’H-2,5’-bibenzo[d]imidazole

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

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

C33H28ClN5

C33H28ClN5

Conditions
ConditionsYield
Stage #1: 5-chloro-1,7’-dimethyl-2’-propyl-1H,3’H-2,5’-bibenzo[d]imidazole With sodium hydroxide In water; acetone for 0.5h;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In water; acetone at 25℃;
90%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

(Z)-4'-(bromomethyl)-N'-hydroxy-[1,1'-biphenyl]-2-carboxamidine

(Z)-4'-(bromomethyl)-N'-hydroxy-[1,1'-biphenyl]-2-carboxamidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium methylate In tetrahydrofuran; methanol at 20 - 30℃; Solvent; Reagent/catalyst; Temperature;89.9%
With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 25 - 80℃; Reagent/catalyst; Solvent; Temperature;85.4%
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

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

2-nitro-aniline
88-74-4

2-nitro-aniline

4'-((2-nitrophenylamino)methyl)biphenyl-2-carbonitrile

4'-((2-nitrophenylamino)methyl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Reflux;89%

114772-54-2Relevant articles and documents

An efficient, commercially viable, and safe process for preparation of losartan potassium, an angiotensin II receptor antagonist

Madasu, Suri Babu,Vekariya,Koteswaramma, Ch,Islam, Aminul,Sanasi, Paul Douglas,Korupolu, Raghu Babu

, p. 2025 - 2030 (2012)

An efficient, commercially viable and safe process for the preparation of losartan potassium, an antihypertensive drug substance, with an overall yield of 55.5% and ~99.9% purity (including five chemical reactions and two recrystallizations) and meeting all other regulatory requirements is described. Formation and control of all the possible impurities are also described.

Bacterial Peptide deformylase inhibition of cyano substituted biaryl analogs: Synthesis, in vitro biological evaluation, molecular docking study and in silico ADME prediction

Khan, Firoz A. Kalam,Patil, Rajendra H.,Shinde, Devanand B.,Sangshetti, Jaiprakash N.

, p. 3456 - 3463 (2016)

Herein, we report the synthesis and screening of cyano substituted biaryl analogs 5(a–m) as Peptide deformylase (PDF) enzyme inhibitors. The compounds 5a (IC50value?=?13.16?μM), 5d (IC50value?=?15.66?μM) and 5j (IC50value?=?19.16?μM) had shown good PDF inhibition activity. The compounds 5a (MIC range?=?11.00–15.83?μg/mL), 5b (MIC range?=?23.75–28.50?μg/mL) and 5j (MIC range?=?7.66–16.91?μg/mL) had also shown potent antibacterial activity when compared with ciprofloxacin (MIC range?=?25–50?μg/mL). Thus, the active derivatives were not only potent PDF inhibitors but also efficient antibacterial agents. In order to gain more insight on the binding mode of the compounds with PDF, the synthesized compounds 5(a–m) were docked against PDF enzyme of Escherichia coli and compounds exhibited good binding properties. In silico ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates.

Readily Reconfigurable Continuous-Stirred Tank Photochemical Reactor Platform

Blacker, A. John,Francis, Daniel,Kapur, Nikil,Marsden, Stephen P.

supporting information, (2022/01/12)

A new modular photochemical continuous stirred-tank reactor (CSTR) design is described, based upon the development of light-source units that can be fitted to the previously described fReactor CSTR platform. In addition to use in homogeneous photochemical reactions (e.g., photoredox-catalyzed hydroamination), these units are especially well suited to handling multiphasic mixtures, exemplified here in solid-liquid (Wohl-Ziegler bromination) and gas-liquid (photocatalytic oxidative decarboxylation) reactions. The use of slurries as input feeds allows for the intensification of photochemical brominations, while the modular nature of the system facilitates the simple integration of downstream reaction steps, exemplified here in a continuous synthesis of an intermediate for the antihypertensive drug valsartan.

Preparation method of normal-temperature bromoethyl cyanobiphenyl based on dibromohydantoin

-

Paragraph 0037-0057, (2020/07/13)

The invention discloses a preparation method of normal-temperature bromoethyl cyanobiphenyl based on dibromohydantoin, and belongs to the technical field of pharmaceutical chemicals, and particularlydiscloses a method for preparing substituent-containing bromoethyl cyanobiphenyl by using a flowing photochemical method. According to the method, an oxidant and a radical initiator are not needed; methyl biphenyl is used as a raw material, dibromohydantoin is used as a bromination reagent, acetone, dichloromethane, petroleum ether or acetonitrile is used as a solvent, and after the raw material and the bromination reagent are respectively mixed with the solvent, the mixture flows into a pipeline through an injection pipe, is mixed by a mixer, then enters a constant-temperature water bath reactor and is subjected to a reaction through illumination. The 2-cyano-4 '-bromomethylbiphenyl synthesized by the method is good in purity, high in yield, simple in reaction system and low in toxicity,is suitable for industrial application in the field of biological medicines, can be suitable for an automatic continuous production process, and conforms to the development concepts of green chemicalindustry, high efficiency and economy.

Preparation method of bromo-sartan biphenyl based on hydrogen peroxide-hydrobromic acid system

-

Paragraph 0036-0056, (2020/07/15)

The invention discloses a preparation method of bromo-sartan biphenyl based on a hydrogen peroxide-hydrobromic acid system, and belongs to the technical field of pharmaceutical chemicals. The invention discloses a method for preparing substituent-containing bromo-sartan biphenyl by using a flowing photochemical method. According to the method, methyl biphenyl is used as a raw material, hydrobromicacid is used as a bromination reagent, hydrogen peroxide is used as an oxidation reagent, acetonitrile or ethyl acetate is used as a solvent, and after the raw material, the bromination reagent and the oxidation reagent are respectively mixed with the solvent, the mixture flows into a pipeline through an injection pipe, is mixed through a mixer, enters a constant-temperature water bath reactor and undergoes a reaction through illumination. The 2-cyano-4'-bromomethylbiphenyl synthesized by the method is good in purity, high in yield, simple in a reaction system, low in toxicity and high in atom conversion rate, is suitable for industrial application in the field of biological medicines, can be suitable for an automatic continuous production process, and conforms to the development conceptsof green chemical industry, high efficiency and economy.

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