13080-85-8

Basic information

• Product Name: 4,4'-Bis(4-aminophenoxy)biphenyl
• Synonyms: 4,4'-(1,1'-BIPHENYL-4,4'-DIYLDIOXY)DIANILINE;4,4'-(P-BIPHENYLENEDIOXY)DIANILINE;4,4'-BIS(4-AMINOPHENOXY)BIPHENYL;BAPB;4,4-BIS(4-AMINOPHENOXY)BIPHENYL(44BAPOBP) 98%;4,4'-Bis(4-aminophenoxy)biphenyl;4,4'-(1,1'-Biphenyl-4,4'-diylbisoxy)bisaniline;4,4'-(Biphenyl-4,4'-diylbisoxy)bis(aniline)
• CAS NO: 13080-85-8
• Molecular Formula: C₂₄H₂₀N₂O₂
• Molecular Weight: 368.43
• EINECS: 1312995-182-4
• Product Categories: Biphenyl & Diphenyl ether;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials
• Mol File: 13080-85-8.mol

Chemical Properties

• Melting Point: 197-200 °C(lit.)
• Boiling Point: 571.365 °C at 760 mmHg
• Flash Point: 321.516 °C
• Appearance: /
• Density: 1.226 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.10±0.10(Predicted)
• CAS DataBase Reference: 4,4'-Bis(4-aminophenoxy)biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(4-aminophenoxy)biphenyl(13080-85-8)
• EPA Substance Registry System: 4,4'-Bis(4-aminophenoxy)biphenyl(13080-85-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13080-85-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

4,4'-bis(4-nitrophenoxy)biphenyl (17095-00-0) → 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8)

Conditions	Yield
With hydrogen; nickel; triethylamine In ethyl acetate at 20 - 60℃; under 11400.8 Torr; Reagent/catalyst; Inert atmosphere;	99%
With hydrogenchloride; tin(ll) chloride In water at 60℃; for 3h;	63%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → 4,4'-bis(4-aminophenoxy)biphenyl-3,3'-disulfonic acid (500295-67-0)

Conditions	Yield
With sulfuric acid at 50℃;	100%
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl With sulfuric acid at 0℃; Heating; Stage #2: With fuming sulfuric acid at 0 - 50℃; for 2.5h;

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 4-hydroxy-benzaldehyde (123-08-0) → C38H28N2O4

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	93.4%

4-chloromethoxybenzene (623-12-1) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → N-(4-methoxyphenyl)-4-{4-[4-(4-methoxyanilino)phenoxy]phenyl}phenoxyaniline

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	93%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 4-chlorobenzaldehyde (104-88-1) → C38H26Cl2N2O2

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	92.7%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + chlorobenzene (108-90-7) → N-phenyl-4-{4-[4-(4-anilinophenoxy)phenyl]phenoxy}aniline

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	91%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 4-nitrobenzaldehdye (555-16-8) → C38H26N4O6

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	89.2%

4-(4-nitrophenoxy)benzaldehyde (50961-54-1) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → C50H34N4O8

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	88.3%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 4-dimethylamino-benzaldehyde (100-10-7) → C42H38N4O2

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	86.9%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 4-Diethylaminobenzaldehyde (120-21-8) → C46H46N4O2

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	82.7%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + phenol (108-95-2) → 4,4'-bis(4-hydroxyphenyldiazenyl-4-phenoxy)biphenyl

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl With hydrogenchloride; sodium nitrite In water at 5℃; Stage #2: phenol With sodium carbonate; sodium hydroxide In water at 5℃; for 5h;	72%

2-methylchlorobenzene (95-49-8) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → N-(4-{4-[4-(4-aminophenoxy)phenyl]phenoxy}phenyl)-2-methylaniline

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In tetrahydrofuran at 65℃; for 4h;	68%

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + benzaldehyde (100-52-7) → C38H28N2O2

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	63.7%

diethylenetriaminepentaacetic dianhydride (23911-26-4) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → C38H39N5O10 (1364601-70-6)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	33%

4-(p-nonylphenoxy)benzaldehyde + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → C68H72N2O4

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 100 - 110℃; for 2h;	30.3%

maleic anhydride (108-31-6) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → C32H20N2O6

Conditions	Yield
Stage #1: maleic anhydride; 4,4'-bis(4-aminophenoxy)biphenyl In acetone at 25℃; for 0.5h; Stage #2: With magnesium acetate; acetic anhydride; triethylamine In acetone for 1h; Heating;

3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride (2540-99-0) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene (210492-48-1) → Polymer; Monomer(s): 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene; 3,3\,,4,4\-diphenylsulfonetetracarboxylic dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl

Conditions	Yield
Stage #1: 3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride; 4,4'-bis(4-aminophenoxy)biphenyl; 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: at 120 - 250℃; for 1.16667h;

3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride (2540-99-0) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → Polymer; Monomer(s): 3,3\,,4,4\-diphenylsulfonetetracarboxylic dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl

Conditions	Yield
Stage #1: 3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride; 4,4'-bis(4-aminophenoxy)biphenyl In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: at 120 - 250℃; for 1.16667h;

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 5-(4-acetoxybenzamido)-isophthaloyl dichloride (250267-73-3) → polymer, Mw=48740, Mn=21600; Monomer(s): 5-(4-acetoxybenzamido)isophthaloyl chloride; 4-{4-[4-(p-aminophenoxy)phenyl]phenoxy}aniline

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one

phthalic anhydride (85-44-9) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + 1,3-bis(3,4-dicarboxyphenoxy)benzene (18959-91-6) → C86H50N4O14

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; 1,3-bis(3,4-dicarboxyphenoxy)benzene In 1-methyl-pyrrolidin-2-one Stage #2: phthalic anhydride Stage #3: Heating;

phthalic anhydride (85-44-9) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer, Mw 2.4E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether Stage #2: phthalic anhydride at 280℃;

phthalic anhydride (85-44-9) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer, Mw 1.3E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether Stage #2: phthalic anhydride at 280℃;

phthalic anhydride (85-44-9) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer, Mw 0.8E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether Stage #2: phthalic anhydride at 280℃;

phthalic anhydride (85-44-9) + 4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) → C40H24N2O6

Conditions	Yield
Stage #1: phthalic anhydride; 4,4'-bis(4-aminophenoxy)biphenyl In 1-methyl-pyrrolidin-2-one Stage #2: Heating;

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer, Mw 2.0E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether Stage #2: at 280℃;

4,4'-bis(4-aminophenoxy)biphenyl (13080-85-8) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer, Mw 2.9E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl

Conditions	Yield
Stage #1: 4,4'-bis(4-aminophenoxy)biphenyl; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether Stage #2: at 280℃;

Upstream product

• 17095-00-0 4,4'-bis(4-nitrophenoxy)biphenyl 

Downstream Products

• 500295-67-0 4,4'-bis(4-aminophenoxy)biphenyl-3,3'-disulfonic acid 

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