86-30-6 Usage
Description
N-Nitrosodiphenylamine is the N-nitroso analogue of diphenylamine, which was once used as a rubber additive but is no longer due to its undesirable carcinogenic effects. It is currently classified as a probable carcinogen by the United States Environmental Protection Agency (EPA) with genetic toxicity.
Uses
Used in Historical Rubber Industry:
N-Nitrosodiphenylamine was historically used as a rubber additive for its properties, but its use has been discontinued due to its carcinogenic effects.
Used in Environmental and Food Contaminant Monitoring:
N-Nitrosodiphenylamine is listed as a drinking water contaminant candidate list 3 (CCL 3) compound by the EPA, indicating its importance in monitoring environmental and food contaminants for public health and safety.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
N-Nitrosodiphenylamine may be sensitive to moisture at elevated temperatures in strongly acidic solutions. May react vigorously with oxidizing agents. May undergo trans-nitrosation reactions with secondary amines .
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition N-Nitrosodiphenylamine emits toxic fumes of nitrogen oxides.
Fire Hazard
Flash point data for N-Nitrosodiphenylamine are not available; however, N-Nitrosodiphenylamine is probably combustible.
Flammability and Explosibility
Nonflammable
Safety Profile
Moderately toxic by
ingestion. An eye irritant. Questionable
carcinogen with experimental carcinogenic
and tumorigenic data. Human mutation data
reported. Dangerous fire hazard when
exposed to heat, flame, or oxidzing
materials. Can react vigorously with
oxidizing materials. When heated to
decomposition it emits highly toxic fumes of
NOx,. See also NITROSAMINES.
Potential Exposure
N-Nitrosodiphenylamine is not a naturally
occurring substance; it is a man-made chemical that is
no longer produced in the United States. It was used in the
manufacture of plastics, resins, rubber and synthetic textiles;
to help control processes involved in making rubber
products, such as tires and mechanical goods; however, in
the early 1980s, the United States manufacturers stopped
producing N-nitrosodiphenylamine because new and more
efficient chemicals were found to replace its uses. In addition,
the use of N-nitrosodiphenylamine had several undesirable
side effects which do not occur with the
replacement chemicals.
Carcinogenicity
Two feeding experiments with NDPhA in rats were totally
negative (no tumors). One used daily doses of 120 mg/kg
body weight to a total dose of 65 g/kg, and another used
a lower dose for only 53 weeks. Another experiment
involved larger groups of rats and mice and higher doses. In
mice, after 2 years, there was occasional hyperplasia of the
bladder mucosa, but no tumors; in rats given 4000 mg
NDPhA/kg diet for 2 years, 16/45 males and 40/49 females
had transitional cell carcinomas of the bladder. IARC classified
NDPhA as not classifiable as to carcinogenicity in
humans (Group 3).
Environmental fate
Chemical/Physical. At temperatures greater than 85 °C, technical grades may decompose to
nitrogen oxides (IARC, 1978). N-Nitrosodiphenylamine will not hydrolyze because it does not
contain a hydrolyzable functional group (Kollig, 1993).
At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 510,
120, 91, and 38 mg/g, respectively (Dobbs and Cohen, 1980).
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Contact with reducing
agents may form hydrazine; hydrogen bromide. Light sensitive;
rapidly decomposes.
Waste Disposal
Burn in admixture with flammable
solvent in furnace equipped with afterburner and
scrubber.
Check Digit Verification of cas no
The CAS Registry Mumber 86-30-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 86-30:
(4*8)+(3*6)+(2*3)+(1*0)=56
56 % 10 = 6
So 86-30-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H10.H2N2O/c1-3-7-11(8-4-1)12-9-5-2-6-10-12;1-2-3/h1-10H;(H2,1,3)
86-30-6Relevant articles and documents
One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives
Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
, p. 1152 - 1163 (2021/01/14)
The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.
Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
supporting information, p. 7415 - 7418 (2020/07/15)
Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is
4-amino diphenylamine preparation method
-
Paragraph 0024-0065, (2019/04/06)
The invention discloses a 4-amino diphenylamine preparation method which includes the steps: slowly dropping concentrated hydrochloric acid into concentrated sulfuric acid, drying generated HCl gas bythe concentrated sulfuric acid and then leading the HCl gas into n-butyl alcohol for absorbing the gas; adding diphenylamine, sodium nitrite, water and methylbenzene, dissolving the diphenylamine bystirring, and then dropping hydrogen chloride for reaction with n-butyl alcohol solution; performing standing and liquid separation, removing water phase and organic phase vacuum desolvation agents, adding water, stirring the solution and performing suction filtration, washing and drying to obtain 4-nitroso diphenylamine; adding the 4-nitroso diphenylamine into an autoclave, adding solvents and catalysts, replacing air in the autoclave by hydrogen and performing hydrogenation reaction; filtering catalyzed hydrogenation liquid, decompressing the desolvation agents and finally performing rectification to obtain 4-amino diphenylamine. According to the preparation method, under the condition of low and medium pressure, composite skeleton nickel catalysts replace traditional noble metal catalysts for hydrogenation reduction of 4-amino diphenylamine, waste gas, waste water and industrial residues are fewer, environmental protection is benefited, and production cost is reduced.