4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline supplier

Name
4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline
EINECS 235-985-8
CAS No. 13080-86-9
Article Data12
CAS DataBase
Density 1.178 g/cm³
Solubility Very slightly soluble in water. Soluble in acetone, Dimethyl sulfoxide(DMSO).
Melting Point 127-130 °C
Formula C₂₇H₂₆N₂O₂
Boiling Point 587.1 °C at 760 mmHg
Molecular Weight 410.516
Flash Point 322.8 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 2,2-Bis[p-(4-aminophenoxy)phenyl]propane;4,4'-[Isopropylidenebis(1,4-phenylene)dioxy]dianiline;BAPP;Bisphenol Abis(4-aminophenyl) ether;2,2-Bis[4-(4-aminophenoxy)phenyl]propane;Aniline,4,4'-[isopropylidenebis(p-phenyleneoxy)]di- (7CI,8CI);
PSA 70.50000
LogP 7.92390

Synthetic route

: 20653-11-6
2,2-bis(4-(4-nitrophenoxy)phenyl)propane

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

Conditions

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%

: 20653-11-6
2,2-bis(4-(4-nitrophenoxy)phenyl)propane

: 7803-57-8
hydrazine hydrate

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

Conditions

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%

: 80-05-7
BPA

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

Conditions

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

: 100-00-5
4-chlorobenzonitrile

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

Conditions

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

: 350-46-9
4-Fluoronitrobenzene

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

Conditions

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: di-tert-butyl dicarbonate

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 2,2'-bis{4-[4-(t-butoxycarbonylamino)phenoxy]phenyl}propane

Conditions

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

: 796974-65-7
1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

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: 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

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%

: 796974-65-7
1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

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: 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

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%

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 90-02-8
salicylaldehyde

: 35948-25-5
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

: 1166187-87-6
P-BAPP-HB

Conditions

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

...Expand

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 1236010-44-8
1,1'-{(propane-2,2-diyl)bis[(1,4-phenylene)oxy(1,4-phenylene)iminomethyl]}bis(2-naphthol)

Conditions

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

: 796974-65-7
1,3-bis(4-bromobenzoyl)-5-tert-butylbenzene

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

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: 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

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: 4-chlorophthalic anhydride

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 2,2'-bis[4-(4'-(4-chlorophthalimido)phenyloxy)phenyl]propane

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 90-02-8
salicylaldehyde

: 2,2'-{propane-2,2-diylbis[(p-phenylene)oxy-(p-phenylene)iminomethyl]}-diphenol

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 61960-57-4
3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoylchloride

: 1333382-36-7
C49H36N4O8

Conditions

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

4-(N-acetylamino)-1-nitrosobezene: 4-(N-acetylamino)-1-nitrosobezene

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 1531603-52-7
2,2-bis{4-[4-(4-acetamidophenyldiazenyl)phenoxy]phenyl}propane

Conditions

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

: 50-00-0
formaldehyd

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 4-dihydrochromeno[6,7-e][1,3]oxazin-8(2H)-one

Conditions

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

...Expand

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 250267-73-3
5-(4-acetoxybenzamido)-isophthaloyl dichloride

polymer, Mw=65700, Mn=25280; Monomer(s): 5-(4-acetoxybenzamido)isophthaloyl chloride; 4-{4-[(4-(p-aminophenoxy)phenyl)dimethylmethane]phenoxy}aniline: polymer, Mw=65700, Mn=25280; Monomer(s): 5-(4-acetoxybenzamido)isophthaloyl chloride; 4-{4-[(4-(p-aminophenoxy)phenyl)dimethylmethane]phenoxy}aniline

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 82684-68-2
1,4-bis[4-(carbonochloridoyl)phenyl] benzene-1,4-dicarboxylate

polymer; monomer(s): 1,4-bis(p-aminophenoxyphenyl)2,2-isopropane; terephthaloyl-bis(4-oxybenzoylchloride): polymer; monomer(s): 1,4-bis(p-aminophenoxyphenyl)2,2-isopropane; terephthaloyl-bis(4-oxybenzoylchloride)

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 96123-43-2
terephthaloyl-bis(oxy-3-benzoyl chloride)

polymer, Mn=37900 g/mol, Mw/Mn=2.5; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; isophthaloyl-bis(4-oxybenzoylchloride): polymer, Mn=37900 g/mol, Mw/Mn=2.5; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; isophthaloyl-bis(4-oxybenzoylchloride)

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 116038-58-5
terephthaloyl-bis(3-oxybenzoyl-chloride)

polymer, Mn=58100 g/mol, Mw/Mn=3.7; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; terephthaloyl-bis(3-oxybenzoylchloride): polymer, Mn=58100 g/mol, Mw/Mn=3.7; monomer(s): 1,4-bis(p-aminophenoxyphenyl)-2,2-isopropane; terephthaloyl-bis(3-oxybenzoylchloride)

Conditions

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

: 7,7'-methylenebis(2-phenyl-3,1-benzoxazin-4-one)

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

polymer; monomer(s): 7,7-methylenebis(2-phenyl-3,1-benzoxazin-4-one); 2,2-bis[4-(4-aminophenyloxy)phenyl]propane: polymer; monomer(s): 7,7-methylenebis(2-phenyl-3,1-benzoxazin-4-one); 2,2-bis[4-(4-aminophenyloxy)phenyl]propane

Conditions

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 38103-06-9
4,4'-bis(4,4'-isopropylidene diphenoxy)-bis(phthalic anhydride)

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: 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

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 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: polymer; monomer(s): 5,5-(1,3-phenylenedioxy)bis(1,3-isobenzofurandione); 2,2-bis[4-(4-aminophenyloxy)phenyl]propane

Conditions

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;

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 2420-87-3
3,3',4,4'-biphenyltetracarboxylic anhydride

polymer, polyamic acid, polycondensation equimolar amount of monomers; monomer(s): 3,3,,4,4-biphenyltetracarboxylic dianhydride; 2,2-[bis[4-(4-aminophenyl)phenyl]]propane: 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

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

: 13080-86-9
2,2-bis-{4-(4-aminophenoxy)phenyl}propane

: 2421-28-5
dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid

polymer, polyamic acid, polycondensation equimolar amount of monomers; monomer(s): 3,3,,4,4-benzophenonetetracarboxylic dianhydride; 2,2-[bis[4-(4-aminophenyl)phenyl]]propane: 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

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

4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline Specification

The IUPAC name of 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline is 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline. With the CAS registry number 13080-86-9, it is also named as 2,2'-Bis(4-aminophenoxyphenyl)propane. The product's categories are Organics; Miscellaneous; Bisphenol A type Compounds (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research, and the other registry number is 158066-25-2. In addition, its molecular formula is C₂₇H₂₆N₂O₂ and molecular weight is 410.51.

The other characteristics of this product can be summarized as: (1)EINECS: 235-985-8; (2)ACD/LogP: 5.19; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): 5.01; (5)ACD/LogD (pH 7.4): 5.18; (6)ACD/BCF (pH 5.5): 3422.21; (7)ACD/BCF (pH 7.4): 5127.43; (8)ACD/KOC (pH 5.5): 10491.47; (9)ACD/KOC (pH 7.4): 15719.17; (10)#H bond acceptors: 4; (11)#H bond donors: 4; (12)#Freely Rotating Bonds: 8; (13)Index of Refraction: 1.641; (14)Molar Refractivity: 125.76 cm³; (15)Molar Volume: 348.4 cm³; (16)Surface Tension: 49.3 dyne/cm; (17)Density: 1.178 g/cm³; (18)Flash Point: 322.8 °C; (19)Melting Point: 127-130 °C; (20)Enthalpy of Vaporization: 87.67 kJ/mol; (21)Boiling Point: 587.1 °C at 760 mmHg; (22)Vapour Pressure: 9.1E-14 mmHg at 25 °C.

Uses of 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline: it can react with benzene-1,4-dicarbaldehyde to get C₇₀H₅₆N₄O₄.

This reaction needs chlorobenzene at temperature of 20 °C for 18 hours. The yield is 90 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also harmful if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
(1)SMILES: O(c1ccc(cc1)C(c3ccc(Oc2ccc(N)cc2)cc3)(C)C)c4ccc(cc4)N
(2)InChI: InChI=1/C27H26N2O2/c1-27(2,19-3-11-23(12-4-19)30-25-15-7-21(28)8-16-25)20-5-13-24(14-6-20)31-26-17-9-22(29)10-18-26/h3-18H,28-29H2,1-2H3
(3)InChIKey: KMKWGXGSGPYISJ-UHFFFAOYAK

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD	skin	> 8gm/kg (8000mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	National Technical Information Service. Vol. OTS0533991,
rat	LD50	oral	308mg/kg (308mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. OTS0533991,

Product Name

4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline

Synthetic route

4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline Specification

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