101-87-1

Basic information

• Product Name: N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE
• Synonyms: 4-Benzenediamine,N-cyclohexyl-N’-phenyl-1;Antioxidant4010;flexzone6h;n-cyclohexyl-n’-phenyl-4-benzenediamine;n-cyclohexyl-n’-phenyl-p-phenylendiamine;n-cyclohexyl-n’-phenyl-p-phenylenediamin;n-cyklohexyl-n’-fenyl-p-fenylendiamin;n-fenyl-n’-cyklohexyl-p-fenylendiamin
• CAS NO: 101-87-1
• Molecular Formula: C₁₈H₂₂N₂
• Molecular Weight: 266.38
• EINECS: 202-984-9
• Product Categories: Industrial/Fine Chemicals
• Mol File: 101-87-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 118-119 °C
• Boiling Point: 399.58°C (rough estimate)
• Flash Point: 275.9 °C
• Appearance: White powder
• Density: 0.9274 (rough estimate)
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.40±0.20(Predicted)
• CAS DataBase Reference: N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE(101-87-1)
• EPA Substance Registry System: N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE(101-87-1)

Safety Data

• Hazardous Substances Data: 101-87-1(Hazardous Substances Data)

Usage

Description

N-Phenyl-N'-Cyclohexyl-p-Phenylenediamine (CPPD) is a rubber chemical used as an antioxidant. Cross reactions are frequently observed with isopropylphenylparaphenylenediamine (lPPD).

Uses

N-Phenyl-N''-cyclohexyl-p-phenylenediamine (>90%) is an antioxidant CPPD; used in preparation method of degradable sealant.

Contact allergens

CPPD is a rubber chemical used as an antioxidant. Crossreactions are frequently observed with N-isopropylNphenylparaphenylenediamine (IPPD).

Synthetic route

N-(4-chlorophenyl)aniline (1205-71-6) + cyclohexylamine (108-91-8) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; sodium t-butanolate In toluene at 110℃; for 19h; Inert atmosphere; chemoselective reaction;	94%

N-phenylphenylene-1,4-diamine (101-54-2) + phenol (108-95-2) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With Pd/C; sodium formate In toluene at 100℃; for 24h; Inert atmosphere;	45%

N,N'-diphenyl-1,4-phenylenediamine (74-31-7) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With acetic acid; platinum at 120℃; under 1471.02 Torr; Hydrogenation;
With nickel at 200 - 220℃; under 128714 Torr; Hydrogenation;

cyclohexanone (108-94-1) + 4-(Phenylazo)diphenylamine (101-75-7) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With platinum on activated charcoal at 160℃; under 73550.8 Torr; Hydrogenation;

4-ntrophenyl(phenyl)amine (836-30-6) + cyclohexanol (108-93-0) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With nickel at 60 - 100℃; Hydrogenation;

Na2 S2 O4 + 4-(phenylimino)cyclohexa-2,5-dienone (2406-04-4) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With methanesulfonic acid In toluene

prop-2-ene-1-thiol (870-23-5) + N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → 3-(allylsulfanyl)-N1-cyclohexyl-N4-phenyl-1,4-benzenediamine

Conditions	Yield
Stage #1: N-cyclohexyl-N'-phenyl-p-phenylenediamine With magnesium sulfate; silver(l) oxide In toluene at 25℃; for 15h; Stage #2: prop-2-ene-1-thiol In ethanol at 25℃;	63%

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N-cyclohexyl-N,N'-dinitroso-N'-phenyl-p-phenylenediamine (27982-47-4)

Conditions	Yield
With hydrogenchloride; sodium nitrite

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → [1,4]benzoquinone-(N-cyclohexyl oxime )-(N-phenyl oxime ) (112600-09-6)

Conditions	Yield
With Perbenzoic acid

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N-cyclohexyl-N'-phenyl-1,4-benzoquinonediimine (52870-44-7, 73334-90-4, 73334-91-5)

Conditions	Yield
With K3Fe(CN)6 in an alkaline medium
With silver(II) oxide

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N4-cyclohexyl-2-methyl-N7-phenyl-2,3-dihydro-1-benzothiophene-4,7-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 63 percent / ethanol / 25 °C 2.1: 53 percent / 150 - 155 °C View Scheme

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N5-cyclohexyl-N8-phenyl-5,8-thiochromanediamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 63 percent / ethanol / 25 °C 2.1: 11 percent / 150 - 155 °C View Scheme

Upstream product

• 836-30-6 4-ntrophenyl(phenyl)amine 
• 108-93-0 cyclohexanol 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 108-95-2 phenol 
• 1205-71-6 N-(4-chlorophenyl)aniline 
• 108-91-8 cyclohexylamine 
• 2406-04-4 4-(phenylimino)cyclohexa-2,5-dienone 
• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 108-94-1 cyclohexanone 
• 101-75-7 4-(Phenylazo)diphenylamine 

Downstream Products

• 27982-47-4 N-cyclohexyl-N,N'-dinitroso-N'-phenyl-p-phenylenediamine 
• 112600-09-6 [1,4]benzoquinone-(N-cyclohexyl oxime )-(N-phenyl oxime ) 
• 52870-44-7 N-cyclohexyl-N'-phenyl-1,4-benzoquinonediimine 

Relevant articles and documents

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.

Preparation of N-substituted-N'-phenyl p-phenylenediamines

The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: STR1 comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: STR2 and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula: in the presence of methanol wherein R1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: STR3 wherein R2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.

2-Propanol derivatives as corrosion inhibitors

New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.