3282-99-3

Basic information

• Product Name: 1,1-BIS(4-AMINOPHENYL)CYCLOHEXANE
• Synonyms: 4-(1-(4-aminophenyl)cyclohexyl)benzenamine;4'-cyclohexylidenedianiline;4-[1-(4-aminophenyl)cyclohexyl]aniline;4,4'-CYCLOHEXYLIDENEDIANILINE;4,4'-DIAMINO DIPHENYL-1,1'-CYCLOHEXANE;1,1-BIS(4-AMINOPHENYL)CYCLOHEXANE;4,4'-Diamino-1,1-Diphenylcyclohexane;1,1-DI-(4'-AMINOPHENYL)CYCLOHEXANE
• CAS NO: 3282-99-3
• Molecular Formula: C₁₈H₂₂N₂
• Molecular Weight: 266.38
• EINECS: 221-926-3
• Product Categories: Intermediates of Dyes and Pigments;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 3282-99-3.mol

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 450.918 °C at 760 mmHg
• Flash Point: 271.711 °C
• Appearance: /
• Density: 1.112 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 5.35±0.10(Predicted)
• CAS DataBase Reference: 1,1-BIS(4-AMINOPHENYL)CYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(4-AMINOPHENYL)CYCLOHEXANE(3282-99-3)
• EPA Substance Registry System: 1,1-BIS(4-AMINOPHENYL)CYCLOHEXANE(3282-99-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 3282-99-3(Hazardous Substances Data)

Usage

Uses

1. Used as an Azo Dye:
1,1-Bis(4-aminophenyl)cyclohexane is used as an azo dye in the textile industry for coloring fabrics due to its vibrant color-producing properties. Its mutagenicity allows for the creation of a wide range of hues, making it a valuable component in the dye manufacturing process.
2. Used in Chemical Synthesis:
In the chemical industry, 1,1-Bis(4-aminophenyl)cyclohexane serves as a key intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a versatile building block for creating complex molecules with specific properties and applications.
3. Used in Research and Development:
Due to its mutagenic properties, 1,1-Bis(4-aminophenyl)cyclohexane is also utilized in research and development for studying the effects of aromatic amines on genetic material. This helps in understanding the mechanisms of mutagenesis and the potential risks associated with exposure to such compounds.
4. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1,1-Bis(4-aminophenyl)cyclohexane may also find applications in the pharmaceutical industry, potentially as a starting material for the synthesis of various drug candidates or as a component in the development of novel therapeutic agents.

Synthetic route

4,4'-(cyclohexane-1,1-diyl)bis(N-(diphenylmethylene)aniline) (1333216-15-1) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
Stage #1: 4,4'-(cyclohexane-1,1-diyl)bis(N-(diphenylmethylene)aniline) With hydrogenchloride; water In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In water	90%

cyclohexanone (108-94-1) + aniline (62-53-3) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
With toluene at 115℃; for 8h; Temperature; Reagent/catalyst;	89.8%
With hydrogenchloride In water at 150℃; for 48h;	60%
With hydrogenchloride; ethanol
With hydrogenchloride at 140 - 150℃;
With phosphoric acid at 140 - 150℃;

aniline hydrochloride (142-04-1) + cyclohexanone (108-94-1) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
With toluene at 110℃; for 8h; Temperature;	55.3%
In water at 150℃; for 22h;

4-(cyclohex-1-enyl)phenylamine (1747-75-7) + aniline hydrochloride (142-04-1) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

cyclohexanone (108-94-1) + aniline (62-53-3) → 4-(cyclohex-1-enyl)phenylamine (1747-75-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
With hydrogenchloride at 200℃;
With hydrogenchloride; ethanol
With hydrogenchloride at 200℃;

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + cyclohexanone (108-94-1) + aniline (62-53-3) → 4-(cyclohex-1-enyl)phenylamine (1747-75-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + water (7732-18-5) + cyclohexanone (108-94-1) + aniline (62-53-3) → 4-(cyclohex-1-enyl)phenylamine (1747-75-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

hydrogenchloride (7647-01-0) + 4-(cyclohex-1-enyl)phenylamine (1747-75-7) + aniline (62-53-3) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
at 100℃;

1,1-bis-(4-amino-phenyl)-3-methyl-cyclohexane (138966-59-3) → 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acid 2: hydrochloric acid; alcohol View Scheme
Multi-step reaction with 2 steps 1: acid 2: concentrated hydrochloric acid; alcohol View Scheme

1-bromo-2,4,5-trimethylbenzene (5469-19-2) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → N,N'-(4,4'-(cyclohexane-1,1-diyl)bis(4,1-phenylene))bis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) (1293383-79-5)

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 80℃; for 18h;	94%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) + 6-bromo-1,4-benzodioxane (52287-51-1) → C50H46N2O8

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; DPEphos; sodium t-butanolate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	82.1%

bromobenzene (108-86-1) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis(4-anilinophenyl) cyclohexane (167218-34-0)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 10h; Inert atmosphere;	81%

9-(1-pentylhexyl)-1H-2-benzopyrano[6′,5′,4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)tetrone + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C88H80N4O8

Conditions	Yield
With 1H-imidazole at 140℃; for 4h; Schlenk technique; Inert atmosphere;	77.26%

1-bromo-3,5-dimethoxybenzene (20469-65-2) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C50H54N2O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	76.8%

4-Bromoveratrole (2859-78-1) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C50H54N2O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	75.2%

1-Bromo-2,4-dimethoxybenzene (17715-69-4) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C50H54N2O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	74.9%

2-bromo-1,3-benzoxazole (68005-30-1) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C32H28N4O2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 2h; Inert atmosphere; Reflux;	74%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C50H54N2O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	73.5%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) + 4-bromo-N,N-bis-(4-methoxyphenyl)aniline (194416-45-0) → C98H90N6O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	72.1%

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C54H62N2O12

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 8h; Inert atmosphere;	71.9%

C24H20BrNO2 + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C114H98N6O8

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100 - 108℃; for 7h; Inert atmosphere;	71.9%

iodobenzene (591-50-4) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis[4-(N,N-diphenyl)aminophenyl]cyclohexane (145024-29-9)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 20h; Ullmann coupling; Inert atmosphere;	64%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1'-cyclohexane-1,1-diylbis(4-bromobenzene)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; Inert atmosphere; Darkness;	64%

1-bromo-4-methoxynaphthalene (5467-58-3) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → C62H54N2O4

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 100 - 108℃; for 10h; Inert atmosphere;	60.5%

4-methyl-4-(trichloromethyl)cyclohexa-2,5-dien-1-one (3274-12-2) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1-<4-<1-(4'-p-Toluidinophenyl)cyclohexyl>imino>-4-methyl-4-trichloromethyl-2,5-cyclohexadiene (131822-52-1) + C34H32Cl6N2 (129332-89-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating; 24-28 h;	A 12% B 60%

para-iodoanisole (696-62-8) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 4,4'-(cyclohexane-1,1-diyl)bis[N,N-bis-(4-methoxyphenyl)aniline] (143765-12-2)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 150℃; for 48h; Inert atmosphere; Schlenk technique;	57%
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 20h; Ullmann coupling; Inert atmosphere;	45%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1′-cyclohexane-1,1-diylbis(4-iodobenzene) (146823-30-5)

Conditions	Yield
Stage #1: 1,1-bis-(4-aminophenyl)cyclohexane With sulfuric acid; sodium nitrite In water at 0℃; for 3h; Stage #2: With potassium iodide In water at 50℃; for 6h;	54%
Stage #1: 1,1-bis-(4-aminophenyl)cyclohexane With sulfuric acid; sodium nitrite In water at 0℃; for 2h; Stage #2: With potassium iodide In water at 50℃; for 6h;	40%
Stage #1: 1,1-bis-(4-aminophenyl)cyclohexane With sulfuric acid; sodium nitrite In water at 0℃; for 2h; Stage #2: With potassium iodide In water at 50℃; for 12h;	34%

phthalic anhydride (85-44-9) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 2,2'-[cyclohexane-1,1-diylbis(4,1-phenylene)]bis(1H-isoindole-1,3(2H)-dione)

Conditions	Yield
With acetic acid for 12h; Reflux;	54%

4-tolyl iodide (624-31-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis[4-(di-p-tolylamino)phenyl]cyclohexane (58473-78-2)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 150℃; for 48h; Inert atmosphere; Schlenk technique;	54%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) + 2,2'-bipyridine-5-carbonyl chloride (140447-00-3) → N,N'-bis(2,2'-bipyridyl-5-yl)carbonyl-1,1-bis(4-aminophenyl)cyclohexane (884303-65-5)

Conditions	Yield
With triethylamine In dichloromethane for 15h; Heating;	53%

1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → 1,1-bis[4-(N,N′-di(tert-butoxycarbonyl)guanidinephenyl)]cyclohexane (1443793-79-0)

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 0℃; for 2h;	52%

4-iodoanisol (529-28-2) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis{4-[N,N-bis(2-methoxyphenyl)]aminophenyl}cyclohexane (1358822-44-2)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 20h; Ullmann coupling; Inert atmosphere;	50%

3-methoxy-1-iodobenzene (766-85-8) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis{4-[N,N-bis(3-methoxyphenyl)]aminophenyl}cyclohexane (1358822-45-3)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 20h; Ullmann coupling; Inert atmosphere;	37%

oxalic acid (144-62-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → {4-[1-(4-amino-phenyl)-cyclohexyl]-phenyl}-oxalamic acid

Conditions	Yield
With water
With chloroform
With chloroform
With water

Upstream product

• 1747-75-7 4-(cyclohex-1-enyl)phenylamine 
• 142-04-1 aniline hydrochloride 
• 108-94-1 cyclohexanone 
• 62-53-3 aniline 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 138966-59-3 1,1-bis-(4-amino-phenyl)-3-methyl-cyclohexane 
• 1333216-15-1 4,4'-(cyclohexane-1,1-diyl)bis(N-(diphenylmethylene)aniline) 

Downstream Products

• 1747-75-7 4-(cyclohex-1-enyl)phenylamine 
• 6373-50-8 p-cyclohexylaniline 
• 6051-38-3 [1,1';1',1'']tercyclohexane-4,4''-diyldiamine 
• 62-53-3 aniline 
• 131822-52-1 1-<4-<1-(4'-p-Toluidinophenyl)cyclohexyl>imino>-4-methyl-4-trichloromethyl-2,5-cyclohexadiene 
• 129332-89-4 C₃₄H₃₂Cl₆N₂ 
• 884303-65-5 N,N'-bis(2,2'-bipyridyl-5-yl)carbonyl-1,1-bis(4-aminophenyl)cyclohexane 
• 28627-52-3 N-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ylidene)benzenamine 
• 138966-59-3 1,1-bis-(4-amino-phenyl)-3-methyl-cyclohexane 
• 385837-09-2 4-(2-methyl-cyclohex-1-enyl)-aniline 
• 3290-24-2 3-ethyl-2-propylquinoline 
• 138966-59-3 (-)-1,1-bis-(4-amino-phenyl)-3-methyl-cyclohexane 
• 1293383-79-5 N,N'-(4,4'-(cyclohexane-1,1-diyl)bis(4,1-phenylene))bis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) 
• 1352733-65-3 C₆₆H₇₈N₂O₈ 

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