13080-86-9

Basic information

• Product Name: 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline
• Synonyms: 4,4'-((Propane-2,2-diylbis(4,1-phenylene))bis(oxy))dianiline;2,2'-Di-[4-(4-aminophenyloxy)phenyl]-propane;2,2'-Bis(4-aminophenoxyphenyl)propane(BAPP);BAPP;2,2'-BIS[4-(4-AMINOPHENOXY)PHENYL]PROPANE;2,2-BIS[4-(4-AMINOPHENOXY)PHENYL]PROPANE;4,4'-ISOPROPYLIDENEBIS[(4-AMINOPHENOXY)BENZENE];4,4'-[ISOPROPYLIDENEBIS(P-PHENYLENEOXY)]DIANILINE
• CAS NO: 13080-86-9
• Molecular Formula: C₂₇H₂₆N₂O₂
• Molecular Weight: 410.51
• EINECS: 235-985-8
• Product Categories: Organics;Miscellaneous;Bisphenol A type Compounds (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;API
• Mol File: 13080-86-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 127-130 °C(lit.)
• Boiling Point: 587.1 °C at 760 mmHg
• Flash Point: 322.8 °C
• Appearance: /
• Density: 1.178 g/cm³
• Vapor Pressure: 0-0Pa at 20-25℃
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.16±0.10(Predicted)
• Water Solubility: Very slightly soluble in water. Soluble in acetone, Dimethyl sulfoxide(DMSO).
• CAS DataBase Reference: 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline(13080-86-9)
• EPA Substance Registry System: 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline(13080-86-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CY1062500
• TSCA: Yes
• Hazardous Substances Data: 13080-86-9(Hazardous Substances Data)

Usage

Chemical Properties

4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline is white solid

Uses

Different sources of media describe the Uses of 13080-86-9 differently. You can refer to the following data:
1. It is applied in pharmaceutical industry.
2. 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline is used for preparation polyimide and epoxy resin material.

Synthetic route

2,2-bis(4-(4-nitrophenoxy)phenyl)propane (20653-11-6) → 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9)

Conditions	Yield
With Ni-B/C; hydrazine hydrate In ethanol at 45 - 75℃; for 2h; Reagent/catalyst;	98.2%
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; under 2844.39 Torr; for 24h;	95%
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; under 2844.39 Torr; for 24h;	95%

2,2-bis(4-(4-nitrophenoxy)phenyl)propane (20653-11-6) + hydrazine hydrate (7803-57-8) → 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9)

Conditions	Yield
Stage #1: 2,2-bis[4-(4-nitrophenoxy)phenyl]propane With palladium 10% on activated carbon In ethanol at 50℃; Reflux; Stage #2: hydrazine hydrate In ethanol at 80 - 90℃; for 3h;	85%

BPA (80-05-7) → 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2CO3 2: Zn, AcOH View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; N,N-dimethyl-formamide / 12 h / Reflux 2: palladium 10% on activated carbon; hydrazine / ethanol; water / 12.5 h / 85 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C 2: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h / 20 °C / 2844.39 Torr View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 130 °C / Inert atmosphere 2.1: palladium 10% on activated carbon / ethanol / 2 h / 80 - 90 °C / Inert atmosphere 2.2: 48 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h / 20 °C / 2844.39 Torr View Scheme

4-chlorobenzonitrile (100-00-5) → 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2CO3 2: Zn, AcOH View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 130 °C / Inert atmosphere 2.1: palladium 10% on activated carbon / ethanol / 2 h / 80 - 90 °C / Inert atmosphere 2.2: 48 h / Reflux View Scheme

4-Fluoronitrobenzene (350-46-9) → 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C 2: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h / 20 °C / 2844.39 Torr View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h / 20 °C / 2844.39 Torr View Scheme

di-tert-butyl dicarbonate + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → 2,2'-bis{4-[4-(t-butoxycarbonylamino)phenoxy]phenyl}propane

Conditions	Yield
With triethylamine In tetrahydrofuran at 25 - 45℃; for 6.5h; Inert atmosphere;	99%

1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene (796974-65-7) + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → polymer, Mn 7000, Mw 11000 by GPC; monomer(s): 1,3-bis(4-bromobenzoyl-5-tert-butyl)benzene; 2,2-bis[4-(4-aminophenoxy)phenyl]propane

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In various solvent(s) at 165℃; Hartwig-Buchwald reaction;	98%

1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene (796974-65-7) + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → polymer, Mn 10000, Mw 42000 by GPC; monomer(s): 1,3-bis(4-bromobenzoyl-5-tert-butyl)benzene; 2,2-bis[4-(4-aminophenoxy)phenyl]propane

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In various solvent(s) at 100 - 165℃; Hartwig-Buchwald reaction;	96%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + salicylaldehyde (90-02-8) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → P-BAPP-HB (1166187-87-6)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	95%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1,1'-{(propane-2,2-diyl)bis[(1,4-phenylene)oxy(1,4-phenylene)iminomethyl]}bis(2-naphthol) (1236010-44-8)

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	95%

1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene (796974-65-7) + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → polymer, Mn 37000, Mw 139300 by GPC, intrinsic viscosity 0.249 g/dl at 25 deg C in DMF; monomer(s): 1,3-bis(4-bromobenzoyl-5-tert-butyl)benzene; 2,2-bis[4-(4-aminophenoxy)phenyl]propane

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In various solvent(s) for 24h; Hartwig-Buchwald reaction; Heating;	84%

4-chlorophthalic anhydride + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → 2,2'-bis[4-(4'-(4-chlorophthalimido)phenyloxy)phenyl]propane

Conditions	Yield
With acetic acid for 24h; Heating;	83%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + salicylaldehyde (90-02-8) → 2,2'-{propane-2,2-diylbis[(p-phenylene)oxy-(p-phenylene)iminomethyl]}-diphenol

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	81%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoylchloride (61960-57-4) → C49H36N4O8 (1333382-36-7)

Conditions	Yield
With triethylamine for 1h; Cooling with ice;	69%

4-(N-acetylamino)-1-nitrosobezene + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → 2,2-bis{4-[4-(4-acetamidophenyldiazenyl)phenoxy]phenyl}propane (1531603-52-7)

Conditions	Yield
In acetic acid at 20℃; for 48h;	65%
With acetic acid at 20℃; for 48h;	65%

formaldehyd (50-00-0) + 7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → 4-dihydrochromeno[6,7-e][1,3]oxazin-8(2H)-one

Conditions	Yield
In 1,4-dioxane at 90 - 100℃; for 24h; Inert atmosphere;	57%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 5-(4-acetoxybenzamido)-isophthaloyl dichloride (250267-73-3) → polymer, Mw=65700, Mn=25280; Monomer(s): 5-(4-acetoxybenzamido)isophthaloyl chloride; 4-{4-[(4-(p-aminophenoxy)phenyl)dimethylmethane]phenoxy}aniline

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

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 1,4-bis[4-(carbonochloridoyl)phenyl] benzene-1,4-dicarboxylate (82684-68-2) → polymer; monomer(s): 1,4-bis(p-aminophenoxyphenyl)2,2-isopropane; terephthaloyl-bis(4-oxybenzoylchloride)

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 0 - 20℃;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + terephthaloyl-bis(oxy-3-benzoyl chloride) (96123-43-2) → polymer, Mn=37900 g/mol, Mw/Mn=2.5; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; isophthaloyl-bis(4-oxybenzoylchloride)

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 0 - 20℃;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + terephthaloyl-bis(3-oxybenzoyl-chloride) (116038-58-5) → polymer, Mn=58100 g/mol, Mw/Mn=3.7; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; terephthaloyl-bis(3-oxybenzoylchloride)

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 0 - 20℃;

7,7'-methylenebis(2-phenyl-3,1-benzoxazin-4-one) + 2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) → polymer; monomer(s): 7,7-methylenebis(2-phenyl-3,1-benzoxazin-4-one); 2,2-bis[4-(4-aminophenyloxy)phenyl]propane

Conditions	Yield
With phosphorus pentoxide In various solvent(s) at 20 - 180℃; for 10h;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 4,4'-bis(4,4'-isopropylidene diphenoxy)-bis(phthalic anhydride) (38103-06-9) → polymer, polyamic acid, polycondensation equimolar amount of monomers; monomer(s): 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride; 2,2-[bis[4-(4-aminophenyl)phenyl]]propane

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer; monomer(s): 5,5-(1,3-phenylenedioxy)bis(1,3-isobenzofurandione); 2,2-bis[4-(4-aminophenyloxy)phenyl]propane

Conditions	Yield
Stage #1: 2,2-bis-{4-(4-aminophenoxy)phenyl}propane; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether In 1-methyl-pyrrolidin-2-one at 20℃; for 8h; Stage #2: With pyridine; acetic anhydride; triethylamine In 1-methyl-pyrrolidin-2-one at 20 - 60℃; for 12h;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + 3,3',4,4'-biphenyltetracarboxylic anhydride (2420-87-3) → polymer, polyamic acid, polycondensation equimolar amount of monomers; monomer(s): 3,3,,4,4-biphenyltetracarboxylic dianhydride; 2,2-[bis[4-(4-aminophenyl)phenyl]]propane

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid (2421-28-5) → polymer, polyamic acid, polycondensation equimolar amount of monomers; monomer(s): 3,3,,4,4-benzophenonetetracarboxylic dianhydride; 2,2-[bis[4-(4-aminophenyl)phenyl]]propane

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

Upstream product

• 20653-11-6 2,2-bis[4-(4-nitrophenoxy)phenyl]propane 
• 7803-57-8 hydrazine hydrate 
• 350-46-9 4-Fluoronitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 80-05-7 BPA 

Downstream Products

• 1531603-34-5 2,2-bis{4-[4-(4-aminophenyldiazenyl)phenoxy]phenyl}propane 
• 1531603-52-7 2,2-bis{4-[4-(4-acetamidophenyldiazenyl)phenoxy]phenyl}propane 
• 1333382-36-7 C₄₉H₃₆N₄O₈ 
• 79922-55-7 2,2'-bis-[4-(4-maleimidephenoxy)phenyl]propane 
• 1190053-16-7 BAA 
• 1166187-87-6 P-BAPP-HB 

Relevant articles and documents

Bis(azobenzene) diamines and photomechanical polymers made therefrom

Bis(azo-benzene) diamine monomers and a method of synthesizing the monomers are provided. The bis(azo-benzene) diamine monomers, in combination with amine reactive monomers, form polymers, such as polyimides and copolyimides, having photomechanical and thermomechanical properties.

Multivalent photo-crosslinkable coumarin-containing polybenzoxazines exhibiting enhanced thermal and hydrophobic surface properties

In this study, mono-, bi-, and trivalent coumarin-containing benzoxazine monomers (mono-, di-, and tri-coumarin BZ) were synthesized in high yield and purity by facile Mannich reactions of 4-methyl-7-hydroxycoumarin and paraformaldehyde with aniline, bisphenol A-NH2, and 1,3,5-tri(4-aminobenzene), respectively, in 1,4-dioxane. 1H and 13C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and high resolution mass spectroscopy support the chemical structures of these three benzoxazine monomers. Differential scanning calorimetry (DSC) and FTIR spectroscopy were used to investigate the curing polymerization behavior and photodimerization ([2π + 2π] cycloaddition) of the coumarin units of mono-, di-, and tri-coumarin BZ to form poly(mono-coumarin BZ), poly(di-coumarin BZ), and poly(tri-coumarin BZ), respectively. DSC measurement revealed that the thermal polymerization temperature of coumarin-containing benzoxazine monomers was lower than that of the model compound 3-phenyl-3,4-dihydro-2H-benzooxazine (263°C) which was attributed to the catalytic effect of the coumarin moiety and a strong electron withdrawing electron conjugated CC bond in the coumarin unit. In addition, the glass transition and thermal decomposition temperatures of poly(tri-coumarin BZ) (Tg = 240°C; Td5 = 370°C) were higher than poly(di-coumarin BZ) and poly(mono-coumarin BZ), consistent with the former's higher crosslinking density. In addition, the water contact angles of poly(tri-coumarin BZ) polymers prepared with and without photo-dimerization prior to thermal curing (112 and 110°, respectively) were higher than the corresponding poly(mono-coumarin BZ) and poly(di-coumarin BZ), presumably because of greater degrees of intramolecular hydrogen bonding between the CO units of the coumarin moieties and the phenolic OH units of the benzoxazine rings, resulting in lower surface free energies. Thus, the presence of multivalent photo-crosslinkable coumarin units enhanced the thermal and hydrophobic surface properties of these polybenzoxazines.

Impact of backbone rigidity on the photomechanical response of glassy, azobenzene-functionalized polyimides

Azobenzene-functionalized polyimide materials can directly transduce light into mechanical force. Here, we examine the impact of polymer backbone rigidity on the photomechanical response in a series of linear, azobenzene-functionalized polymers. The rigidity of the backbone was varied by the polymerization of five dianhydride monomers with a newly synthesized diamine (azoBPA-diamine). The azobenzene-functionalized linear polymers exhibit glass transition temperatures (Tg) ranging from 276 to 307 C and maintain excellent thermal stability. The photomechanical response of these materials was characterized by photoinduced cantilever bending as well as direct measurement of photogenerated stress upon exposure to linearly polarized, 445 nm light. Increasing the rigidity of the polymer backbone increases the magnitude of stress that is generated but decreases the angle of cantilever deflection.