1590-80-3

Basic information

• Product Name: N-Octyl-N'-phenyl-1,4-benzenediamine
• Synonyms: N-Octyl-N'-phenyl-1,4-benzenediamine;N-Octyl-N'-phenyl-p-phenylenediamine
• CAS NO: 1590-80-3
• Molecular Formula: C₂₀H₂₈N₂
• Molecular Weight: 296.4497
• Mol File: 1590-80-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 448.3°Cat760mmHg
• Flash Point: 268.4°C
• Appearance: /
• Density: 1.02g/cm³
• CAS DataBase Reference: N-Octyl-N'-phenyl-1,4-benzenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Octyl-N'-phenyl-1,4-benzenediamine(1590-80-3)
• EPA Substance Registry System: N-Octyl-N'-phenyl-1,4-benzenediamine(1590-80-3)

Safety Data

• Hazardous Substances Data: 1590-80-3(Hazardous Substances Data)

Upstream product

• 111-86-4 n-Octylamine 
• 1205-71-6 N-(4-chlorophenyl)aniline 

Relevant articles and documents

Rational and predictable chemoselective synthesis of oligoamines via Buchwald-Hartwig amination of (hetero)aryl chlorides employing Mor-Dalphos

We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl) morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl] 2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl] 2/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a′) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)] + fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH2CH 2CH2(4-C6H4NH2)] +OTf- (7) in 72% yield.

Stabilization of unsaturated carboxylic acid esters with mixtures of polyalkylene-amines and arylenediamines

A method of inhibiting polymerization of unsaturated carboxylic acid esters and improved unsaturated carboxylic acid ester compositions are described. The method comprises, and the compositions are prepared by, incorporating into the ester composition a combination comprising polyalkyleneamine and arylenediamine of the formula STR1 in which X is hydrogen, chloro, trichloromethyl, trifluoromethyl, nitro, lower alkyl, lower alkoxy or phenoxy, R is hydrogen or alkyl, and R1 is alkyl or phenyl or R and R1 together with the nitrogen atom is a heterocycle selected from the group consisting of pyrrolidinyl, 2,5-dimethyl pyrrolidinyl, piperidino and hexahydro-1H-azepin-1-yl.