4-Aminoazobenzene

Base Information

• Chemical Name: 4-Aminoazobenzene
• CAS No.: 60-09-3
• Deprecated CAS: 81691-68-1
• Molecular Formula: C12H11N3
• Molecular Weight: 197.239
• Hs Code.: 29270000
• European Community (EC) Number: 200-453-6
• NSC Number: 2032
• UN Number: 3077
• UNII: 57X2AH42T1
• DSSTox Substance ID: DTXSID6024460,DTXSID40859039
• Nikkaji Number: J485.147A,J2.337J,J2.498.412E
• Wikipedia: Aniline_Yellow
• Wikidata: Q546957
• Metabolomics Workbench ID: 66933
• ChEMBL ID: CHEMBL83761,CHEMBL1429559
• Mol file: 60-09-3.mol

Synonyms:4-(phenyldiazenyl)aniline;aniline yellow;C.I. Solvent Yellow 1;p Aminoazobenzene;p-Aminoazobenzene;para Aminoazobenzene;para-Aminoazobenzene

Chemical Property of 4-Aminoazobenzene

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 123-126 °C(lit.)
• Refractive Index: 1.611
• Boiling Point: 360.7 °C at 760 mmHg
• PKA: 2.82(at 25℃)
• Flash Point: 171.9 °C
• PSA: 50.74000
• Density: 1.12 g/cm³
• LogP: 4.26540
• Water Solubility.: 29.59mg/L(25 oC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 197.095297364
• Heavy Atom Count: 15
• Complexity: 201
• Transport DOT Label: Class 9

Purity/Quality:

99.9% ^*data from raw suppliers

4-Aminoazobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T; N; C
• Hazard Codes: T,N,Xi
• Statements: 45-50/53-36/37/38-20/21/22-46
• Safety Statements: 53-45-60-61-36/37/39-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Azo Dyes
• Canonical SMILES: C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N
• Description: This azoic coloring can be reduced in paraphenylenediamine (PPD). It ean be found in some semipermanent hair dyes, and patch tests are frequently positive (about 30%) in hairdressers with hand dermatitis. Because of cross-sensitivity, the detection of sensitization to p-aminoazobenzene may be assumed by a PPD test.
• Uses: In form of its salts in dyeing; intermediate in manufacture of Acid Yellow, diazo dyes and indulines. as a dye for lacquer, varnish, wax products, oi! stains and styrene res ins; in insecticides; used as an intermediate in the manufacture of Acid Yellow, diazo dyes and indulines.

Technology Process of 4-Aminoazobenzene

There total 130 articles about 4-Aminoazobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

p-nitrophenylbenzotriazene (13113-75-2) + aniline hydrochloride (142-04-1,36663-09-9) + aniline (62-53-3) → 4-nitro-aniline (100-01-6,104810-17-5) + aniline yellow (60-09-3) + disperse orange 3 (730-40-5)

Guidance literature:

at 60 ℃;

Reference yield:

cyclohexane (110-82-7,25012-93-5) + 1,3-Diphenyltriazen (297766-64-4) → N-phenyl-2-cyclohexylamine (1821-36-9) + 4-phenylalanine (92-67-1) + 2-phenylaniline (90-41-5) + diphenylamine (122-39-4) + aniline yellow (60-09-3) + 2-aminoazobenzene (2835-58-7)

Guidance literature:

at 21.9 ℃; for 2.37h; Kinetics; Mechanism; Quantum yield; Irradiation; var. of solvent;

DOI:10.1002/bbpc.19830871214

Reference yield:

mandelic acid-(4-phenylazo-anilide) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) + aniline yellow (60-09-3)

Guidance literature:

upstream raw materials:

quinoline

quinoline hydrochloride

1,3-Diphenyltriazen

formic acid

Downstream raw materials:

N-[4-(phenylazo)phenyl]-acetamide

N-{4-[phenyldiazenyl]phenyl}-N-[phenylmethylene]amine

N-(p-methoxybenzylidene)-p-aminoazobenzene

N-Phenyl-N'-(4-benzolazo-phenyl)-thioharnstoff

Refernces

• 1、 Joshi, Neeraj Kumar,Fuyuki, Masanori,Wada, Akihide. "Polarity controlled reaction path and kinetics of thermal cis-to-trans isomerization of 4-aminoazobenzene". . p. 1891 - 1899. Retrieved 2014.
• 2、 v.Mechel,Stauffer. "-". . p. 151 E,152 E,156 E. Retrieved 1944.
• 3、 Gingrich, Phillip W.,Olson, David E.,Tantillo, Dean J.,Tombari, Robert J.,Tuck, Jeremy R.,Yardeny, Noah. "Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions". supporting information. p. 7575 - 7580. Retrieved 2021/09/22.