Diazoaminobenzene

Base Information

• Chemical Name: Diazoaminobenzene
• CAS No.: 136-35-6
• Molecular Formula: C12H11 N3
• Molecular Weight: 197.239
• Hs Code.: 29270000
• European Community (EC) Number: 205-240-1
• NSC Number: 2077
• UNII: 5T4EEW75HJ
• DSSTox Substance ID: DTXSID9024934
• Nikkaji Number: J5.621I
• Wikipedia: 1,3-Diphenyltriazene
• Wikidata: Q1209248
• NCI Thesaurus Code: C44366
• ChEMBL ID: CHEMBL573540
• Mol file: 136-35-6.mol

Synonyms:1,3-diphenyl-1-triazene;diazoaminobenzene;diphenyl-triazene

Chemical Property of Diazoaminobenzene

Chemical Property:

• Appearance/Colour: ochre powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 96 ºC
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 304.9 ºC at 760 mmHg
• PKA: 1.00±0.30(Predicted)
• Flash Point: 138.2 ºC
• PSA: 36.75000
• Density: 1.07 g/cm³
• LogP: 3.87040
• Storage Temp.: Store below +30°C.
• Solubility.: 0.5g/l insoluble
• Water Solubility.: 499.8mg/L(room temperature)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 197.095297364
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

1,3-Diphenyltriaz-1-ene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Explodes on heating to 150C dangerous.
• Hazard Codes: E,Xn
• Statements: 1-5-20/21/22-36/37/38
• Safety Statements: 15-26-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)NN=NC2=CC=CC=C2
• Description: Diazoaminobenzene (DAAB) is an aromatic amine that is a suspected carcinogen. It is harmful if inhaled, ingested, or absorbed through the skin. It causes skin irritation and severe irritation to eyes. DAAB can be made by diazotizing aniline dissolved in hydrochloric acid with sodium nitrite and then adding a concentrated solution of sodium acetate. DAAB is listed in the US Environmental Protection Agency’s Toxic Substances Control Act Inventory. DAAB has three major use areas: intermediate, complexing agent, and polymer additive. Use as an intermediate is reported in several industry sectors, including organic synthesis, dye manufacture, and agrochemical manufacture (insecticides). DAAB is also a versatile metal complexing agent. A series of metabolism studies in rodents and human liver slices, electron spin resonance spectroscopy studies, short-term dermal toxicity studies in rodents, and acute bone marrow micronucleus studies in mice demonstrated that DAAB is metabolized and shares similar genotoxic and toxicological properties to the known human carcinogen, benzene, and the known rodent carcinogen, aniline.
• Uses: DAAB is used as a chemical intermediate, a complexing agent, and as a polymer additive. DAAB has been used to promote adhesion of natural rubber to steel tire cords. It has also been used as a blowing agent in the production of a foamed polymeric material. In addition, DAAB is used in the manufacture of dyes and insecticides. DAAB is also an impurity in certain color additives used in cosmetics, food products, and pharmaceuticals. In addition, it has been reported to show semiconducting properties and to be useful as a dopant for poly methylmethacrylate in semiconductor manufacture. 1,3-Diphenyltriazene can be used to prepare degradable polyester foam material. Diazoaminobenzene is used as a chemical intermediate, complexing agent, and polymer additive (Mathews and De Costa 1999). It has uses associated with organic synthesis and dye and insecticide manufacture (Lewis 1997), and it is an effective dopant for laser ablation (micro-machining) of polymethylmethacrylate (Bolle et al. 1990). Diazoaminobenzene has been identified as a low-level contaminant in the dyes D&C red no. 33, FD&C yellow no. 5 (tartrazine), and FD&C yellow no. 6; all three are permitted for use in drugs and cosmetics, and the latter two are permitted in food (FDA 2010).

Technology Process of Diazoaminobenzene

There total 4 articles about Diazoaminobenzene 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: 20.3%

→ cis-1,3-diphenyltriazene (136-35-6,297766-64-4,93589-89-0)

Guidance literature:

Reference yield:

cis-1,3-diphenyltriazene (136-35-6,297766-64-4,93589-89-0) → (E)-1,3-diphenyltriaz-1-ene (136-35-6)

Guidance literature:

With phosphate buffer; at 21 ℃; Further Variations:; pH-values; Reagents; buffer concentrations; Kinetics;

DOI:10.1021/jo000599l

Reference yield:

(E)-1,3-diphenyltriaz-1-ene (136-35-6) → cis-1,3-diphenyltriazene (136-35-6,297766-64-4,93589-89-0)

Guidance literature:

In polymer matrix; for 0.00833333h; UV-irradiation;

DOI:10.1016/j.dyepig.2010.06.006

upstream raw materials:

1,3-Diphenyltriazen

cis-1,3-diphenyltriazene

Downstream raw materials:

benzenediazonium

aniline

cis-1,3-diphenyltriazene

Refernces

• 1、 Tabone, Ryan,Barra, Mónica. "Thermal cis-to-trans isomerisation of triazene dyes in doped polymer films". experimental part. p. 180 - 186. Retrieved 2011/01/12.
• 2、 Baro,Dudek,Luther,Troe. "PHOTOCHEMISTRY OF 1,3-DIPHENYLTRIAZENE IN VARIOUS MEDIA. I: PHOTOLYSIS IN LIQUID SOLUTIONS.". . p. 1155 - 1161. Retrieved 2007/10/02.