114772-54-2

Basic information

• Product Name: 4-Bromomethyl-2-cyanobiphenyl
• Synonyms: 4-BroMoMethyl-2-cyanophenyl;4-BroMoMethyl-2-cyanobiphenyl, 98% 5GR;4-(2-Cyanophenyl)benzyl BroMide;4'-Bromomethylbiphenyl-2-carbonitrile 2-Cyano-4'-bromomethylbiphenyl;Br-OTBN;Irbesartan BroMo Cyano IMpurity;4'-(Bromomethyl)-2-cyanobiphenyl, 4-(2-Cyanophenyl)benzyl bromide, 2-[4-(Bromomethyl)phenyl]benzonitrile;4&priMe
• CAS NO: 114772-54-2
• Molecular Formula: C₁₄H₁₀BrN
• Molecular Weight: 272.14
• EINECS: 425-280-5
• Product Categories: Aromatic;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C10 to C27;Chemical Synthesis;Cyanides/Nitriles;Liquid Crystals;Materials Science;Nitrogen Compounds;Organic and Printed Electronics;Organic Building Blocks;cyanide| alkyl bromide;Chemical intermediate for Sartan;Biphenyl derivatives;pharmacetical;INTERMEDIATESOF;Biphenyl & Diphenyl ether;API intermediates;Sartan's serie;Hypertension;Intermediates of Irbesartan;Irbesartan
• Mol File: 114772-54-2.mol
• Article Data: 65

Chemical Properties

• Melting Point: 125-128 °C(lit.)
• Boiling Point: 413.2°Cat760mmHg
• Flash Point: 203.7°C
• Appearance: Cream powder
• Density: 1.43 g/cm³
• Vapor Pressure: 0.1-0.2Pa at 20-25℃
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble in water
• CAS DataBase Reference: 4-Bromomethyl-2-cyanobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromomethyl-2-cyanobiphenyl(114772-54-2)
• EPA Substance Registry System: 4-Bromomethyl-2-cyanobiphenyl(114772-54-2)

Safety Data

• Hazard Codes: Xi,Xn,N
• Statements: 20/21/22-36/37/38-50/53-43
• Safety Statements: 26-36/37-36/37/39-61-60
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• Hazardous Substances Data: 114772-54-2(Hazardous Substances Data)

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.

Synthetic route

2-Cyano-4'-methylbiphenyl (114772-53-1) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

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 (64113-85-5) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
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) + 1,2-dichloro-ethane (107-06-2) + 2,2'-azobis-(4-methoxy-2,4-dimethylvaleronitrile) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
With bromine In water	89.4%
With N-Bromosuccinimide In water	79.6%

2-Cyano-4'-methylbiphenyl (114772-53-1) → 2-(4,4-dibromomethylphenyl)benzonitrile (209911-63-7) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
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) + 2,2'-azobis (2,4-dimethyl valeronitrile) (4419-11-8, 108346-39-0, 108346-40-3) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; water	80.5%

2,2'-azobis(2-methylbutyronitrile) + 2-Cyano-4'-methylbiphenyl (114772-53-1) + chlorobenzene (108-90-7) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
With bromine	75%

2-cyanobenzoic acid (3839-22-3) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

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

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

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

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

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

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

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

Conditions	Yield
In water

sodium bromate + 2,2'-azobis(2-methylbutyronitrile) + 2-Cyano-4'-methylbiphenyl (114772-53-1) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
In water; chlorobenzene
In water; chlorobenzene

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

tetrachloromethane (56-23-5) + 2-Cyano-4'-methylbiphenyl (114772-53-1) + dibenzoyl peroxide (94-36-0) → 4'-bromornethyl-2-cyanobiphenyl + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

azobisisobutyronitrile (34241-39-9) + 2-Cyano-4'-methylbiphenyl (114772-53-1) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
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) + dibenzoyl peroxide (94-36-0) → Losartan ›DUP[753] + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane

2-Cyano-4'-methylbiphenyl (114772-53-1) + dibenzoyl peroxide (94-36-0) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane
With N-Bromosuccinimide In tetrachloromethane

o-cyanobromobenzene (2042-37-7) → 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2)

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

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

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

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

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

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

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

Conditions	Yield
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) + Methyl 3-nitro-4-valerylaminobenzoate (127007-35-6) → 4-[(2'-Cyano-biphenyl-4-ylmethyl)-pentanoyl-amino]-3-nitro-benzoic acid methyl ester (136285-45-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 15h; Ambient temperature;	100%

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) + ethyl butyroyl acetate (3249-68-1) → ethyl 2-<(2'-cyanobiphenyl-4-yl)methyl>-3-oxohexanoate (137860-26-5)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride (137864-24-5)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → N-((2′-cyano[1,1′-biphenyl]-4-yl)methyl)-N-phenylpentanamide

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

Conditions	Yield
	96%

methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate hydrochloride (1206680-19-4) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-cyano-4'-[2"-n-propyl-4"-methyl-6"-methylcarboxylate-benzimidazole-1"-ylmethyl]biphenyl (1098100-86-7)

Conditions	Yield
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) + 2-Mercaptobenzothiazole (149-30-4) → 4'-(benzothiazol-2-ylsulfanylmethyl)-biphenyl-2-carbonitrile (721970-96-3)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → C29H20FN3S2 (1429045-99-7)

Conditions	Yield
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) + methyl 4-hydroxylbenzoate (99-76-3) → methyl 4-[(2'-cyanobiphenyl-4-yl)methoxy]benzoate

Conditions	Yield
With potassium carbonate In butanone at 78 - 80℃; for 2h;	93.5%

2-butyl-4-(4-fluorophenyl)-1H-imidazole-5-carbaldehyde (1313233-70-3) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4'-[{2-butyl-4-(4-fluorophenyl)-5-formyl-1H-imidazol-1-yl}methyl]biphenyl-2-carbonitrile (1313233-71-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	93.2%

Ethyl 3-oxoheptanoate (7737-62-4) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-(2'-Cyano-biphenyl-4-ylmethyl)-3-oxo-heptanoic acid ethyl ester (137860-02-7)

Conditions	Yield
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) + (6-Butyl-2-oxo-1,2-dihydro-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (147876-57-1) → 6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-1,2-dihydro-2-oxo-3-tert-butoxycarbonylaminomethyl pyridine (147876-52-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane for 72h; Heating;	92%

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) + dimethyl amine (124-40-3) → 4'-((dimethylamino)methyl)-[1,1'-biphenyl]-2-carbonitrile (1000930-96-0)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 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	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 6h;	92%

benzoimidazole (51-17-2) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4′-((1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carbonitrile (136285-25-1)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-(2'-Cyano-biphenyl-4-ylmethyl)-5-methyl-3-oxo-hexanoic acid ethyl ester (137860-48-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 15h; Heating;	91%

2-propyl-1H-benzimidazole (5465-29-2) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile (136285-23-9)

Conditions	Yield
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) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → C22H15N3S (1429045-94-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	91%

1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → hydrobromide 4'-(3,4-dihydropyrimido[1,2-a]benzimidazole-10(2H)-ylmethyl) biphenyl-2-carbonitrile

Conditions	Yield
In nitromethane for 7.5h; Heating;	91%

7-amino-4-(azidomethyl)-2H-chromen-2-one (1186293-68-4) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → C24H17N5O2

Conditions	Yield
With sodium carbonate In acetone for 6h; Reflux;	90.5%

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

Conditions	Yield
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'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4'-((4-hydroxyphenylamino)methyl)biphenyl-2-carbonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	90%

4-trifluoromethylphenylamine (455-14-1) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4'-((4-(trifluoromethyl)phenylamino)methyl)biphenyl-2-carbonitrile

Conditions	Yield
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 + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → C33H28ClN5

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

Conditions	Yield
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) + 2-nitro-aniline (88-74-4) → 4'-((2-nitrophenylamino)methyl)biphenyl-2-carbonitrile

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

Upstream product

• 114772-53-1 4'-Methyl-2-cyanobiphenyl 
• 114772-51-1 Tolyl Isocyanate 
• 114772-40-6 tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate 
• 114772-38-2 Methyl 4'-bromomethyl biphenyl-2-carboxylate 
• 114772-36-0 TERT-BUTYL 4'-METHYLBIPHENYL-2-CARBOXYLATE 
• 114772-34-8 Methyl 4'-methylbiphenyl-2-carboxylate 
• 114772-33-7 Methyl 3-(4-Methylphenyl)benzoate 
• 114772-25-7 2-BUTYL-1H-IMIDAZOLE-4,5-DICARBONITRILE 
• 114772-19-9 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE 
• 1147706-81-7 BenzenaMine, 4-(2-Methyl-2,7-diazaspiro[3.5]non-7-yl)- 
• 114769-18-5 2H-Pyran-2-carbonyl chloride, 3,4-dihydro- (9CI) 
• 114768-72-8 Coumarin 521T 
• 114767-84-9 2[4(-N-OCTYLOXY)-PHENYL)-5-N-OCTYLOXY-PYRIMIDINE 
• 114767-15-6 4-aminophenylphosphonic acid methyl-1,2,2-trimethylpropyl diester 

Downstream Products

• 114772-55-3 4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile 
• 114772-78-0 (4'-METHYL-1,1'-BIPHENYL-2-YL)METHANOL 
• 1147732-37-3 (R)-3-(4-hydroxyphenyl)-hex-4-ynoic acid 
• 114773-44-3 sodium 2-(2-butyl-1-{4-[(2-carboxybenzoyl)amino]benzyl}-4-chloro-1H-imidazol-5-yl)propanoate 
• 1147737-68-5 1,4-di-tert-butyl-2,5-bis(2,2,2-trifluoroethoxy)benzene 
• 114773-97-6 2-ACETYLTHIOPHENE O-METHYLOXIME 
• 114774-06-0 2-Acetyl-5-nitrothiophene O-methyl oxime, 98% 
• 114774-08-2 2-Acetyl-5-[1-(methoxyimino)ethyl]thiophene 
• 114774-09-3 5-(1-Methoxyiminoethyl)-2-thiophenecarboxylic acid 
• 1147748-91-1 AMINO-(3-BROMO-4-HYDROXY-PHENYL)-ACETIC ACID 
• 1147753-38-5 1-Methyl-7-azaindole-4-carboxylic acid 
• 114776-15-7 2-CHLORO-4-FLUORO-5-NITROBENZOIC ACID 
• 114776-28-2 bepafant 
• 1147-76-8 5-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PENTANOIC ACID 

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