4-(Dimethylamino)azobenzene

Base Information

• Chemical Name: 4-(Dimethylamino)azobenzene
• CAS No.: 60-11-7
• Deprecated CAS: 55964-95-9,77126-00-2,77126-00-2
• Molecular Formula: C14H15N3
• Molecular Weight: 225.293
• Hs Code.: 29270000
• European Community (EC) Number: 200-455-7
• ICSC Number: 1498
• NSC Number: 6236
• UN Number: 2811,3143,3077
• UNII: A49L8E13FD
• DSSTox Substance ID: DTXSID5020491
• Nikkaji Number: J1.922D,J2.203.933D,J2.203.934B
• Wikipedia: Methyl_yellow
• Wikidata: Q416956
• NCI Thesaurus Code: C44324
• Metabolomics Workbench ID: 51086
• ChEMBL ID: CHEMBL263116,CHEMBL1090440
• Mol file: 60-11-7.mol

Synonyms:4 Dimethylaminoazobenzene;4-Dimethylaminoazobenzene;Butter Yellow;Dimethylaminoazobenzene;Methyl Yellow;p Dimethylaminoazobenzene;p-Dimethylaminoazobenzene;p-Dimethylaminoazobenzene, (E)-Isomer;p-Dimethylaminoazobenzene, (Z)-Isomer

Chemical Property of 4-(Dimethylamino)azobenzene

Chemical Property:

• Appearance/Colour: yellow to orange crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 111 °C (dec.)(lit.)
• Refractive Index: 1.567
• Boiling Point: 371.1 °C at 760 mmHg
• PKA: 3.226(at 25℃)
• Flash Point: 178.2 °C
• PSA: 27.96000
• Density: 1.02 g/cm³
• LogP: 4.16800
• Storage Temp.: Store at RT.
• Solubility.: Solubility Insoluble in water; soluble in ethanol, benzene, ethe
• Water Solubility.: 13.6 mg/L
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 225.126597491
• Heavy Atom Count: 17
• Complexity: 236
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Solvent yellow 2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-40-68-45-23/24/25
• Safety Statements: 36/37-45-53-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Azo Dyes
• Canonical SMILES: CN(C)C1=CC=C(C=C1)N=NC2=CC=CC=C2
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. This substance is possibly carcinogenic to humans.
• Description: 4-N,N-Dimethylaminobenzene diazonium chloride is a diazo compound found in diazo copy paper. It is allergenic only when unexposed.
• Uses: For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0). Formerly used as a coloring agent in foods, drugs, and cosmetics Butter yellow was largely used as a food coloring agent. It was also used for the determination of free hydrochloric acid in gastric juice, for the spot test identification of peroxidized fats, as a pH indicator, and as a laboratory reagent.

Technology Process of 4-(Dimethylamino)azobenzene

There total 39 articles about 4-(Dimethylamino)azobenzene 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: 100.0%

4-amino-N,N-dimethylaniline (99-98-9) + Nitrosobenzene (586-96-9) → methyl yellow (60-11-7)

Guidance literature:

With acetic acid; In ethanol; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1002/adsc.202100440

Reference yield: 86.0%

benzenediazonium tetrafluoroborate (369-57-3) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → methyl yellow (60-11-7)

Guidance literature:

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In benzene; for 1h; Ambient temperature;

DOI:10.1246/cl.1981.579

Reference yield: 86.0%

benzenediazonium (2684-02-8) + 1-(4-N,N'-dimethylaminophenyl)-1-propanol (82946-80-3) → methyl yellow (60-11-7)

Guidance literature:

In ethanol; water; at 8 ℃; for 6h;

upstream raw materials:

benzenediazonium

N,N-dimethyl-aniline

phenyldiazonium acetate

aniline

Downstream raw materials:

N,N-dibutyl-N',N'-dimethyl-p-phenylenediamine

N,N-dimethyl-4-(phenyl-trans-azo)-aniline-N-oxide

N-phenyl benzoyl amide

benzamide

Refernces

• 1、 Nakano, Hideyuki,Akamatsu, Keiichi,Moriwaki, Kazuyuki,Shirota, Yasuhiko. "Photochromic behavior in the molecular glass of 4,4′,4″-tris(3-methylphenyphenylamino)triphenylamine". . p. 701 - 702. Retrieved 1996.
• 2、 Moriwaki, Kazuyuki,Kusumoto, Mitsushi,Akamatsu, Keiichi,Nakano, Hideyuki,Shirota, Yasuhiko. "Photochromic reaction in a molecular glass as a novel host matrix: The 4-dimethylaminoazobenzene-4,4′,4″-tris [3-methylphenyl(phenyl)amino]triphenylamine system". . p. 2671 - 2676. Retrieved 1998.
• 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.
• 4、 Cao, Guiyan,Hu, Yulai,Huang, Danfeng,Huo, Congde,Liu, Xuan,Su, Yingpeng,Wang, Ke-Hu,Yu, Jie,Zhang, Rong,Zhao, Yanan. "Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds". supporting information. p. 1103 - 1112. Retrieved 2020/04/01.