728039-63-2

Basic information

• Product Name: Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine
• Synonyms: Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine;N,N-Bis([1,1'-biphenyl]-4-yl)-4'-bromo-[1,1'-biphenyl]-4-amine;N-[1,1'-Biphenyl]-4-yl-N-(4'-broMo-[1,1'biphenyl-4-yl)-[1,1'-Biphenyl]-4-aMine;N,N-Di([1,1'-biphenyl]-4-yl)-4'-broMo-[1,1'-biphenyl]-4-aMine;BTBPA;[1,1'-Biphenyl]-4-amine,N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-;4'-Bromotri(4-biphenylyl)amine;[1,1'-Biphenyl]-4-amine, N,N-bis([1,1'-biphenyl]-4-yl)-4'-bromo-
• CAS NO: 728039-63-2
• Molecular Formula: C₃₆H₂₆BrN
• Molecular Weight: 552.50234
• Mol File: 728039-63-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 225.0 to 229.0 °C
• Boiling Point: 703.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.277±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -3.44±0.60(Predicted)
• CAS DataBase Reference: Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine(728039-63-2)
• EPA Substance Registry System: Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine(728039-63-2)

Safety Data

• Hazardous Substances Data: 728039-63-2(Hazardous Substances Data)

Usage

General Description

Bisbiphenyl-4-yl-(4'-bromo-biphenyl-4-yl)-amine is a chemical compound that consists of two biphenyl groups linked together with a central amine group and a bromo substitution at the 4' position. Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine belongs to the class of biphenylamines and is often used in research and industrial applications for its unique properties. It is a white to off-white powder with a molecular formula C24H19BrN and a molecular weight of 383.32 g/mol. Bisbiphenyl-4-yl-(4'-bromo-biphenyl-4-yl)-amine is commonly utilized as a building block in the synthesis of various organic compounds and materials, and it has potential applications in the fields of pharmaceuticals, agrochemicals, and material sciences due to its diverse reactivity and functionality.

Synthetic route

4-bromo-4'-iodobiphenyl (105946-82-5) + bis(biphenyl-4-yl)amine (102113-98-4) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Reflux;	90%
With palladium diacetate; triphenylphosphine; sodium t-butanolate In toluene at 80℃; for 8h; Inert atmosphere;	83%
With copper(l) iodide; 1,10-Phenanthroline; potassium tert-butylate In toluene at 100℃; for 48h; Inert atmosphere;	82%

4-(4-bromophenyl)bromobenzene (92-86-4) + bis(biphenyl-4-yl)amine (102113-98-4) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
With palladium diacetate; triphenylphosphine; sodium t-butanolate In toluene Inert atmosphere; Reflux;	78%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Reflux;	75%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene at 80℃; for 25h; Inert atmosphere;	74%

N,N-di-(4-biphenyl)benzylamine (462631-32-9) + palladium-active carbon + palladium (7440-05-3) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + bis(biphenyl-4-yl)amine (102113-98-4)

Conditions	Yield
With hydrogen In ethanol; dichloromethane; chloroform; toluene

bis(triphenylphosphine)palladium(II) dichloride + 4-(4-bromophenyl)bromobenzene (92-86-4) + bis(biphenyl-4-yl)amine (102113-98-4) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; water; toluene
In 5,5-dimethyl-1,3-cyclohexadiene; water
In 5,5-dimethyl-1,3-cyclohexadiene; water; toluene

→ N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine / toluene / 7 h / 20 - 120 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / chloroform; ethanol / 0.5 h / 20 °C 3.1: sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 130 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / 3 h / 90 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 24 h / 100 °C 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / 100 °C View Scheme

4,4'-diiodobiphenyl (3001-15-8) + bis(biphenyl-4-yl)amine (102113-98-4) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 24h; Inert atmosphere;	9.1 g

N,N-di-(4-biphenyl)benzylamine (462631-32-9) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / chloroform; ethanol / 0.5 h / 20 °C 2: sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 130 °C / Inert atmosphere View Scheme

4-Aminobiphenyl (92-67-1) → N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / 3 h / 90 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 24 h / 100 °C 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / 100 °C View Scheme

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) → C60H42N2O2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 46h;	100%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + bis(pinacol)diborane (73183-34-3) → N,N-bis({[1,1'-biphenyl]-4-yl})-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-amine (1421701-43-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene Reflux;	84%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene Reflux;	84%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene Reflux;	84%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	77%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + C43H51NO4 → C79H76N2O4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; hexane at 100℃; for 2h; Inert atmosphere;	92%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + C28H18BrN → C64H43BrN2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 17h; Inert atmosphere;	91%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-phenyl-1-triphenylenylamine → C60H42N2

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 140℃; for 24h; Inert atmosphere;	90%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + bis(biphenyl-4-yl)amine (102113-98-4) → N,N,N',N'-tetra[(1,1'-biphenyl)-4-yl]-(1,1'-biphenyl)-4,4'-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 24h;	80%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-[1,1′-biphenyl]-3-yl[1,1′-biphenyl]-3-amine → C60H44N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 24h;	79%

3-aminodibenzofuran (4106-66-5) + N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) → C48H34N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 5h; Inert atmosphere;	78.42%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-([1,1′-biphenyl]-4-yl)-[1,1′:4′,1″-terphenyl]-4-amine (897921-63-0) → C66H48N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Inert atmosphere; Reflux;	77%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Reflux;	77%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + 2-{bis(biphenyl-4-yl)amino}phenylboronic acid → 2,4''-bis{bis(biphenyl-4-yl)amino}-1,1':4',1"-terphenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 20h; Inert atmosphere; Reflux;	76%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + 9-((4-diphenylamino)phenyl)-9H-carbazol-2-yl-2-boronic acid → bis-biphenyl-4-yl-{4'-[9-(4-diphenylaminophenyl)-9H-carbazol-2-yl]biphenyl-4-yl}amine

Conditions	Yield
With palladium diacetate; potassium carbonate In tetrahydrofuran; water at 60℃; for 12h; Inert atmosphere;	75%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-phenyl-[1,1':4',1"-terphenyl]-4-amine (897671-81-7) → C60H44N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Inert atmosphere; Reflux;	75%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Reflux;	75%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + C33H22N2O → C69H47N3O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux;	75%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + 5,5-Dimethyl-5,10-dihydro-benzo<1,8>naphthyridin (90903-64-3) → N,N-di([1,1'-biphenyl]-4-yl)-4'-(5,5-dimethylbenzo[b][1,8]naphthyridine-10(5H)-yl)-[1,1'-biphenyl]-4-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In o-xylene at 120℃; for 12h; Inert atmosphere;	72%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + (9,9-dimethyl-9H-fluoren-3-yl)phenylamine → C57H44N2

Conditions	Yield
Stage #1: N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine; (9,9-dimethyl-9H-fluoren-3-yl)phenylamine for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate for 18h; Inert atmosphere; Reflux;	71%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-([1,1‘-biphenyl]-4-yl)-[1,1‘-biphenyl]-2-amine (1372775-52-4) → C60H44N2 (1608462-65-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene Inert atmosphere; Reflux;	70%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + N-(dibenzofuran-2-yl)-N-phenyl-amine (861317-95-5) → C54H38N2O (1318338-56-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; for 2h; Inert atmosphere;	70%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + 10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole → C56H39N3

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In water; toluene at 100℃; for 24h;	68%

N-[1,1'-biphenyl]-4-yl-N-(4'-bromo[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (728039-63-2) + 10H-benzofuro[3,2-b]indole (248-66-8) → C50H34N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	66%
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	66%

Upstream product

• 92-67-1 4-phenylalanine 
• 462631-32-9 N,N-di-(4-biphenyl)benzylamine 
• 3001-15-8 4,4'-diiodobiphenyl 
• 102113-98-4 bis(biphenyl-4-yl)amine 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 105946-82-5 4-bromo-4'-iodobiphenyl 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 7440-05-3 palladium 

Downstream Products

• 1421701-39-4 C₅₄H₃₆N₂ 
• 1421701-44-1 C₆₀H₄₀N₂ 
• 1011534-43-2 C₅₅H₃₉N₃S 
• 1007387-52-1 C₆₄H₄₆N₂S 
• 1421701-43-0 N,N-bis({[1,1'-biphenyl]-4-yl})-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-amine 

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