136-35-6 Usage
Description
1,3-Diphenyltriazene is an orange solid that is an aromatic amine and a suspected carcinogen. It is harmful if inhaled, ingested, or absorbed through the skin, causing skin irritation and severe irritation to eyes. It can be prepared by diazotizing aniline dissolved in hydrochloric acid with sodium nitrite and then adding a concentrated solution of sodium acetate. 1,3-Diphenyltriazene is listed in the US Environmental Protection Agency’s Toxic Substances Control Act Inventory.
Uses
1. Used in Chemical Intermediates:
1,3-Diphenyltriazene is used as a chemical intermediate in various industry sectors, including organic synthesis, dye manufacture, and agrochemical manufacture (insecticides). It is also a versatile metal complexing agent.
2. Used in Complexing Agents:
As a complexing agent, 1,3-Diphenyltriazene has applications in different industries due to its ability to form stable complexes with metals.
3. Used in Polymer Additives:
1,3-Diphenyltriazene is used as a polymer additive, promoting adhesion of natural rubber to steel tire cords and as a blowing agent in the production of foamed polymeric materials.
4. Used in Dyes and Insecticides:
It has uses associated with the manufacture of dyes and insecticides, contributing to the development and production of these products.
5. Used in Cosmetics, Food Products, and Pharmaceuticals:
1,3-Diphenyltriazene is an impurity in certain color additives used in cosmetics, food products, and pharmaceuticals, playing a role in the coloring of these products.
6. Used in Semiconductor Manufacture:
It has been reported to show semiconducting properties and is useful as a dopant for poly methylmethacrylate in semiconductor manufacture, enhancing the performance of the material.
7. Used in Degradable Polyester Foam Material:
1,3-Diphenyltriazene can be used to prepare degradable polyester foam material, contributing to the development of environmentally friendly packaging and insulation materials.
8. Used in Laser Ablation (Micro-machining):
Diazoaminobenzene, a related compound, has been identified as an effective dopant for laser ablation (micro-machining) of polymethylmethacrylate, which can be applicable to 1,3-Diphenyltriazene as well, depending on its specific properties and behavior in similar processes.
Air & Water Reactions
Dust can be explosive when suspended in air at specific concentrations. Insoluble in water.
Reactivity Profile
1,3-DIPHENYLTRIAZENE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. 1,3-DIPHENYLTRIAZENE explodes when heated to above 150°C. A mixture of the triazine and acetic anhydride exploded violently upon warming, Ber., 1891, 24, 4160.
Health Hazard
ACUTE/CHRONIC HAZARDS: 1,3-DIPHENYLTRIAZENE may explode if subjected to severe shock or heat.
Fire Hazard
Flash point data for 1,3-DIPHENYLTRIAZENE are not available, however, 1,3-DIPHENYLTRIAZENE is probably combustible.
Safety Profile
Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. Strongly
explosive when shocked or heated to 98'C.
Mixture with acetic anhydride explodes
when warmed. When heated to
decomposition it emits toxic fumes of NOx,.
Carcinogenicity
Diazoaminobenzene is reasonably anticipated to be a human carcinogen based on (1) evidence from studies in experimental animals andwith human tissue demonstrating that diazoaminobenzene is metabolized to benzene, a known human carcinogen, and (2) evidence that diazoaminobenzene causes genetic damage. Studies in rats and mice have shown that the metabolism of diazoaminobenzene to benzene is quantitative. Benzene was listed in the First Annual Report onCarcinogens in 1980 based on human epidemiological studies dem-causes cancer at numerous tissue sites in rodents.
Environmental Fate
DAAB is a respiratory tract, skin, and eye irritant. DAAB yields
benzene and aniline as metabolites. The proposed metabolic
pathway forDAAB is that it is cleaved reductively by liver enzymes
or gut flora to form aniline, benzene, and nitrogen. DAAB
metabolism also results in the formation of a reactive phenyl
radical, which could account for an additional risk of toxicity or
carcinogenicity. The erythrocyte and lymphoid systems are major
targets of DAAB toxicity. Induction of lymphoid atrophy of the
thymus and other lymphoid tissues were observed, as well as
methemoglobin formation, accompanying anemia, increased
spleen weights, and regenerative hematopoiesis. Analysis of
organ weights indicated possible chemical-related effects in the
thymus, heart, spleen, kidney, and liver of rats and/or mice.
Increases in the incidences of several skin lesions, including
hyperplasia of the epidermis and hair follicles, and inflammation
in rats and mice and ulceration in female mice were observed.
Toxicity evaluation
DAAB is an aromatic amine that exists as small golden yellow
crystals at room temperature. It is insoluble in water (water
solubility 0.5 g l-1) but freely soluble in ethyl alcohol, ethyl
ether, benzene, pyridine, and hexane. It is stable under normal
temperatures and pressures. DAAB melts at 98°C, decomposes
at 130°C with major decomposition at 188°C, and explodes at
its boiling point of 150°C. When heated to decomposition, it
emits toxic fumes of NOx. The decomposition products of
DAAB include benzene, o- and p-aminodiphenyl, diphenylamine,
and azobenzene.
Check Digit Verification of cas no
The CAS Registry Mumber 136-35-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 136-35:
(5*1)+(4*3)+(3*6)+(2*3)+(1*5)=46
46 % 10 = 6
So 136-35-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H15N3/c1-3-8-14(9-4-1)17-12-7-13-18(16-17)15-10-5-2-6-11-15/h1-12,16H,13H2
136-35-6Relevant articles and documents
Kinetic studies on the thermal cis-trans isomerization of 1,3-diphenyltriazene in aqueous solution. Effects of acids and bases
Barra, Monica,Chen, Nan
, p. 5739 - 5744 (2000)
The thermal cis-to-trans isomerization of 1,3-diphenyltriazene (DPT) has been investigated in buffered aqueous solutions by means of laser-flash photolysis techniques. The cis-to-trans isomerization process is found to be catalyzed by general acids and general bases as a result of acid/base-promoted 1,3-prototropic rearrangements. Acid catalysis is attributed to rate-limiting proton transfer to the nitrogen-nitrogen double bond of cis-DPT, whereas base catalysis is attributed to rate-limiting base-promoted ionization of the amino nitrogen of cis-DPT leading to the isomerization. In addition, a process ascribed to the interconversion of cis rotamers through hindered rotation around the nitrogen-nitrogen single bond is also observed; at high pH this process becomes rate-limiting.
Substituent effects on the thermal cis-to-trans isomerization of 1,3-diphenyltriazenes in aqueous solution
Chen, Nan,Barra, Monica,Lee, Ivan,Chahal, Navjot
, p. 2271 - 2277 (2007/10/03)
The thermal cis-to-trans isomerization of some symmetrically p,p′-disubstituted 1,3-diphenyltriazenes has been studied by means of laser-flash photolysis techniques. The geometric isomerization is catalyzed by general acids and general bases as a result of acid/base-promoted 1,3-prototropic rearrangements. Acid catalysis becomes more prominent as the electron-donating character of the para substituent increases, while base catalysis becomes more important as the electron-withdrawing character of the para substituent increases. In addition, the rate ascribed to the interconversion of neutral cis rotamers through hindered rotation around the nitrogen-nitrogen single bond is found to decrease as the electron-withdrawing character of the para substituent increases. Rates of interconversion of neutral cis rotamers are also found to decrease with decreasing solvent polarity, which is indicative of the involvement of a polar transition state. On the other hand, kinetic investigations of the acid-catalyzed decomposition of target triazenes are consistent with an A1 mechanism.
Treatment of aromatic amines with gas mixtures derived from the oxidation of ammonia to effect diazotization/coupling
-
, (2008/06/13)
1,3-Diaryl triazenes, e.g., 1,3-diphenyltriazene, intermediates in the synthesis of aromatic diamines, e.g., p-phenylenediamine, are prepared by catalytically oxidizing ammonia, and subsequently the resulting nitric oxide, with a gas comprising diluted molecular oxygen, e.g., air, so as to produce a gas mixture containing dilute NOx, i.e., NO2 preferably admixed with NO, x being (1 + n), wherein n is the NO2 fraction of the NOx ; and contacting the gas mixture, preferably at a temperature in the range of about from 25° to 350° C., with excess primary aromatic monoamine, e.g., aniline, so as to result in a monoamine temperature in the range of about from 25° to 90° C., preferably 40° to 60° C., during contact. Highest yields of triazene are obtained when the x in NOx is about from 1.3 to 1.7, and the amount of NOx gas mixture contacted with the monoamine and the time of contact are such that at least about 60% by weight of the monoamine remains unconsumed. A gas mixture temperature just prior to gas contact with the liquid monoamine in the range of about from 110° to 275° C. is more preferred under certain circumstances.
