Basic information
- CAS
136-35-6- Standard SMILES
c1ccc(N=NNc2ccccc2)cc1- InChIKey
ALIFPGGMJDWMJH-UHFFFAOYSA-N- Molecular formula
- C12H11N3
- Average molar mass
- 197.24 g/mol
- Monoisotopic mass
- 197.09529736
Overview
Diazoaminobenzene can cause cancer according to California Labor Code.
Names & identifiers
- Preferred name
- Diazoaminobenzene
- IUPAC
- N-phenyldiazenylaniline
- English name
- Diazoaminobenzene
- Molecular formula
- C12H11N3
- Molecular weight
- 197.24
Names & synonyms
Diazoaminobenzene136-35-61,3-Diphenyltriazene1-Triazene, 1,3-diphenyl-AnilinoazobenzeneBenzeneazoanilineDAAB1,3-DIPHENYL-1-TRIAZENECelloforDiazoaminobenzenp-DiazoaminobenzeneAniline, N-(phenylazo)-
Show more names
cellofor(czech)DiazoaminobenzolBenzene azoanilidebenzenediazoanilide
BenzeneazoanilideDiazobenzeneanilideTriazene, 1,3-diphenyl-DTXSID90249345T4EEW75HJNSC-2077DTXCID704934NSC2077
Database identifiers
- CAS
136-35-6- PubChem CID
- 8689
- DTXSID
DTXSID9024934- ChEMBL
CHEMBL573540- UNII
- 5T4EEW75HJ
- EC Number
- 205-240-1
- Nikkaji
- J5.621I
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 36.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 191
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Other Aromatics (Nitrogen)
Carcinogens
SpringerMaterials PropertiesCrystal structure
Color/FormGOLDEN-YELLOW, SMALL CRYSTALS
Solubility
less than 1 mg/mL at 72 °F (NTP, 1992)
INSOLUBLE IN WATER; FREELY SOLUBLE IN BENZENE, ETHER, HOT ALCOHOL
Boiling Point302 °F at 760 mmHg explodes (NTP, 1992)
Melting Point
208 °F (NTP, 1992)
98 °C
Vapor Density6.8 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Physical Description
1,3-diphenyltriazene is an orange solid. (NTP, 1992)
Golden-yellow solid; [Merck Index] Golden yellow crystalline powder; [MSDSonline]
Collision Cross Section
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Hazard Traits - Carcinogenicity
1-Triazene, 1,3-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire HazardsFlash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This material may explode if subjected to severe shock or heat. (NTP, 1992)
Hazards SummaryExplodes when heated to 150 deg C; [Merck Index] May cause irritation; May induce methemoglobinemia; Targets blood, liver spleen, and GI system; [MSDSonline]
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Special Reports
National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Diazoaminobenzene (136-35-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s057zdia.pdf]
Chemistry & industry
Uses & manufacturing
Uses
Used for organic synthesis, dyes, and insecticides; [Hawley]
ORGANIC SYNTHESIS; DYES; INSECTICIDE
Methods of Manufacturing
BY DIAZOTIZING ANILINE DISSOLVED IN HYDROCHLORIC ACID WITH SODIUM NITRITE AND THEN ADDING A CONCENTRATED SOLUTION OF SODIUM ACETATE: HARTMAN, DICKEY, ORG SYN COLL VOL II 163 (1943).
INTERACTION OF NITROUS ACID AND AN ALCOHOLIC SOLUTION OF ANILINE.
General Manufacturing Information
1-Triazene, 1,3-diphenyl-: ACTIVE
1,3-DIPHENYL-1-TRIAZENE WAS THE MOST ACTIVE OF TWELVE 1,3-DIARYLTRIAZENES TESTED POSTEMERGENCE AT 6 KG/HA AGAINST AMARANTHUS RETROFLEXUS, ARTEMISIA VULGARIS & OTHER COMMON WEEDS.
Applications
DescriptionDiazoaminobenzene (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.
UsesDAAB 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.
Related reactions
1 records
Compound notes
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