91-59-8 Usage
Chemical properties
2-Naphthylamine is also known as β-Naphthylamine, it is white to pink shiny flaky crystal, it is volatile with water vapor. It is harmful, carcinogenic, the International Institute for Cancer Research (IARC) put benzidine, 2-Naphthylamine and 4-aminobiphenyl as a human carcinogen (evidence), we should be particularly careful. The relative density is 1.0614 (98/4℃), m.p. is 111~113℃, boiling point is 306℃. It is insoluble in water, but soluble in hot water, ethanol, ether and benzene etc. Aqueous solution is blue fluorescence. It can be reducted by heat silver nitrate ammonia solution. It is synthesized by 2-naphthol with ammonia and ammonium sulfite in a high pressure system. 2-Naphthylamine is an important dye intermediates, can be used in the manufacture of dyes, phthalocyanine dyes, reactive dyes (Reactive brilliant orange K-7R, active golden XG, active golden KM-G, Reactive Yellow KM-RN, big red group B) and J acid. It can also be used as organic analytical reagents and fluorescent indicator, and also as a synthesis of organic materials.
It can enter from the respiratory tract, gastrointestinal tract and skin. Long-term exposure β-Naphthylamine can cause bladder cancer. It can cause weak stimulation of the skin, contact dermatitis, and methemoglobinemia. After the diagnosis of bladder cancer should be early surgery. Prevention should be carried out from the reform process firstly, 1-naphthylamine acetic acid should be used in place of β-Naphthylamine. Production equipment should be tightly closed to prevent the escape of toxic vapors and dusts.
structure of 2-naphthylamine
Uses
Different sources of media describe the Uses of 91-59-8 differently. You can refer to the following data:
1. Amino and nitrite of Aminonaphthalene can form diazonium salt, and can turn into a variety of hydrocarbon derivatives of naphthalene, it can be used in the manufacture of dyes and organic synthesis, also used as indicators of organic analytical reagents and fluorescent agents.
2. It is listed as a known human carcinogen. Used in manufacturing of dyes, as antioxidant in rubber
3. An amine compound used for research purposes
4. 2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.
Production method
Since the nitration of naphthalene can not obtain 2-nitro-naphthalene, so the producing methods is different from 1-Naphthylamine. 2-Naphthylamine is derived by 2-naphthol pressurized ammonia solution.
Chemical Properties
2-Naphthylamine is a white to red crystals
with a faint, aromatic odor. Darkens in air to a reddish-purple color.
Physical properties
White crystals becomes purplish-red on exposure to air. Odor threshold concentrations ranged
from 1.4 to 1.9 mg/m3 (quoted, Keith and Walters, 1992).
Production Methods
2-Naphthylamine was previously produced in substantial
amounts for nearly 50 years but is no longer produced
commercially. It is now used exclusively for research, and
only rarely. It was formerly used in the manufacture of
dyestuffs and as an antioxidant in the rubber industry.
Prior to termination of its domestic production and use in
the dye and rubber industries, an estimated 1000 U.S. workers
were possibly exposed to 2-naphthylamine by inhalation
and dermal routes. Currently, laboratory technicians and
scientists who use the compound for research purposes may
constitute the group with the greatest risk of potential exposure.
Definition
ChEBI: 2-naphthylamine is a naphthylamine carrying the amino group at position 2. It has a role as a carcinogenic agent.
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 2014, 1953 DOI: 10.1021/ja01104a525Synthesis, p. 830, 1980 DOI: 10.1055/s-1980-29225
General Description
A white to reddish colored solid in the form of flakes. Slightly soluble in hot water and denser than water. Toxic by ingestion, inhalation and skin absorption. Used to make dyes and agricultural chemicals.
Air & Water Reactions
2-Naphthylamine darkens in air to a reddish-purple color (oxidizes). Slightly soluble in hot water and denser than water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].
Reactivity Profile
2-Naphthylamine is a weak base. 2-Naphthylamine is incompatible with strong oxidizing agents and strong acids. 2-Naphthylamine is also incompatible with nitrous acid. 2-Naphthylamine reduces warm ammoniacal silver nitrate.
Hazard
Toxic by ingestion, inhalation, skin absorption; a confirmed carcinogen. Causes bladder cancer.
Health Hazard
2-Naphthylamine poses a severe health haz ard because of its carcinogenicity. Admin istration of this compound by all routesresulted in cancers in various tissues in testanimals. It caused tumors in the kidney, blad der, liver, lungs, skin, and blood tissues.There is sufficient evidence that this com pound causes bladder cancer in humans aftera latent period of several years.The toxicity of 2-naphthylamine is lowto moderate. However, high doses can pro duce severe acute toxic effects. The routesof exposures are ingestion, skin contact, andinhalation of its dusts or vapors. The acutetoxic symptoms are similar to those produced by 1-naphthylamine: hemorrhagic cystitis or methemoglobinemia (causing hypoxiaor inadequate supply of oxygen to tissues),respiratory distress, and hematuria (blood inurine).LD50 value, oral (rats): 727 mg/kg.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Safety Profile
Confirmed human
carcinogen with experimental neoplastigenic
and tumorigenic data. Long and continued
exposure to even small amounts may
produce tumors and cancers of the bladder.
Poison by intraperitoneal route. Moderately
toxic by ingestion. Experimental
reproductive effects. Human mutation data
reported. A very toxic chemical in any of its
physical forms, such as flake, lump, dust,
liquid, or vapor. It can be absorbed into the
body through the lungs, the gastrointestinal
tract, or the skin. Combustible when
exposed to heat or flame. At elevated
temperatures it evolves a vapor that is
flammable and explosive. Incompatible with
nitrous acid. When heated to
decomposition it emits toxic fumes of
NOx.
Potential Exposure
2-Naphthylamine is presently used
only for research purposes. It is present as an impurity in
α-naphthylamine. It is as an intermediate in the preparation
of other compounds. 2-Naphthylamine was widely used in
the manufacture of dyestuffs; as an antioxidant for rubber;
and in rubber coated cables.
Carcinogenicity
2-Naphthylamine is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
Environmental fate
Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine
solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium
and nitrate ions.
Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 2-naphthylamine and
other substituted aromatic hydrocarbons (aniline, toluidine, 1-naphthylamine, phenol, cresol,
pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence of
ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was
cleaved by chloramine forming cyanogen chloride. At lower pHs, the amount of cyanogen
chloride formed increased (Kanno et al., 1982).
2-Naphthylamine 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 300,
150, 75, and 37 mg/g, respectively (Dobbs and Cohen, 1980).
Shipping
UN1650 β-Naphthylamine, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
Purification Methods
Sublime the amine at 180o in a stream of nitrogen. Crystallise it from hot water (charcoal) or *benzene. Dry it under vacuum in a drying pistol. The styphnate has m 194-195o (from EtOH). [Beilstein 12 H 1265, 12 III 2989, 12 IV 3122.] CARCINOGEN.
Incompatibilities
A weak base. Dust may form explosive
mixture with air. 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. Incompatible with nitrous
acid.
Waste Disposal
Controlled incineration
whereby oxides of nitrogen are removed from the effluent
gas by scrubber, catalyst, or thermal device. Consult
with environmental regulatory agencies for guidance on
acceptable disposal practices. Generators of waste containing
this contaminant (≥100 kg/mo) must conform with
EPA regulations governing storage, transportation, treatment,
and waste disposal.
Check Digit Verification of cas no
The CAS Registry Mumber 91-59-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 91-59:
(4*9)+(3*1)+(2*5)+(1*9)=58
58 % 10 = 8
So 91-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
91-59-8Relevant articles and documents
Mutagenicity and aromatic amine content of fumes from heated cooking oils produced in Taiwan
Chiang, Tai-An,Pei-Fen, Wu,Ying, Liao Su,Wang, Li-Fang,Ko, Ying Chin
, p. 125 - 134 (1999)
According to toxicological studies, there are several unidentified mutagens derived from cooking oil fumes appearing in kitchens of Chinese homes where women daily prepare food. Data are limited to an analysis of aromatic amines from cooking oil fumes, which are known to be carcinogenic for bladder cancer. Fume samples from three different commercial cooking oils frequently used in Taiwan were collected and analysed for mutagenicity in the almonella/microsome assay. Aromatic amines were extracted from the samples and identified by HPLC and confirmed by gas chromatography/mass spectrometry (GC/MS). Extracts from three cooking oil fumes were found to be mutagenic in the presence of S-9 mix. All samples contained 2-naphthylamine (2-NA) and 4-aminobiphenyl (4-ABP). Concentrations of 2-NA and 4-ABP were 31.5 and 35.7 μg/m3 in fumes from sunflower oil, 31.9 and 26.4 mg/m3 in vegetable oil, and 48.3 and 23.3 μg/m3 in refined-lard oil, respectively. Mutagenicities of the three cooking oil condensates were significantly reduced (P 0.05) by adding the antioxidant catechin (CAT) into the oils before heating. Significant difference existed between the amounts of aromatic amines with and without adding CAT (P 0.05). These results indicate that exposure to cooking oil fumes in Taiwan might be an important but controllable risk factor in the aetiology of bladder cancer. 1999 Published by Elsevier Science Ltd. All rights reserved.
Novel aminopeptidase specific for glycine from Actinomucor elegans.
Ito, Kiyoshi,Ma, Xiaohang,Azmi, Nik,Huang, Hua-Shan,Fujii, Mikio,Yoshimoto, Tadashi
, p. 83 - 88 (2003)
Glycyl aminopeptidase was purified 600-fold from a cell extract of Actinomucor elegans by ammonium sulfate fractionation and sequential chromatography on DEAE-Toyopearl, Toyopearl HW65C, and FPLC-Superdex 200 HR, with recovery of 3.3% of the activity. The enzyme highly specifically hydrolyzed Gly-X (amino acid, peptide, or arylamide) bonds. The enzyme hydrolyzed other amino acid residues but at a rate of less than one fifth that with Gly. The order was Gly >> Ala >> Met > Arg > Ser > Leu. The Km value for glycyl-2-naphthylamide was 0.24 mM. The enzyme was most active at pH 8.0 with glycyl-2-naphthylamide as the substrate and its optimal temperature was 40 degrees C. The enzyme was inhibited by iodoacetic acid, and p-chloromercuribenzoate but not done by diisopropylfluorophosphate, o-phenanthroline, or EDTA. Magnesium and calcium had no effect on enzymic activity, but the activity was suppressed by cadmium, zinc, and copper ions. The molecular mass was estimated to be 320 kDa by gel filtration on FPLC-Superdex 200 HR and 56.5 kDa by SDS-PAGE, so the enzyme probably was a hexamer.
Inhibitory effects of quaternary ammonium compounds on lysosomal degradation of endogenous proteins
Matsumoto,Watanabe,Suga,Fujitani
, p. 516 - 518 (1989)
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Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 1530 - 1534 (2021/03/08)
The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
Composite of β-cyclodextrin and bentonite clay: a promising support for Pd immobilization and developing a catalyst for hydrogenation of nitroarenes under mild reaction condition
Koohestani, Fatemeh,Sadjadi, Samahe
supporting information, (2020/12/21)
In attempt to take advantages of naturally occurring compounds for the catalysis, a novel composite composed of β-cyclodextrin, dendrimer and bentonite clay is fabricated and utilized as a support for the stabilization of Pd nanoparticles. To prepare the support, bentonite is amino functionalized and then successively reacted with 2,4,6-trichloro-1,3,5-triazine and ethylenediamine to furnish a dendrimer of generation II on bentonite. Afterwards, the terminal functionalities of the dendrimer were adorned with cyclodextrin. Bentonite played role in the heterogenation of the catalyst and improvement of the stability of the composite while, cyclodextrins served as molecular shuttles and capping agent for the as-prepared Pd nanoparticles. Dendrimer with multi nitrogen atoms, on the other hand, improved Pd anchoring through electrostatic interactions. The catalyst was applied for the hydrogenation of nitroarenes under mild reaction condition in aqueous media in a selective manner. Notably, the catalyst could be recovered and reused repeatedly.
