1-Naphthylamine CAS 134-32-7
Introduction：Basic information about 1-Naphthylamine CAS 134-32-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1-Naphthylamine Basic information
| Product Name: | 1-Naphthylamine |
| Synonyms: | alpha-naftylamin(czech);Aminogen I;α-Naphthylamine≥ 98.5% (HPLC);1-Aminophthalene;C.I. 37265;C.I. Azoic Diazo Component 114;c.i.azoicdiazocomponent114;ci37265 |
| CAS: | 134-32-7 |
| MF: | C10H9N |
| MW: | 143.19 |
| EINECS: | 205-138-7 |
| Product Categories: | Building Blocks;C10;Amines;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Chemistry;Aromatics;Intermediates;Fluorescent;134-32-7;bc0001;A |
| Mol File: | 134-32-7.mol |
1-Naphthylamine Chemical Properties
| Melting point | 47-50 °C (lit.) |
| Boiling point | 301 °C (lit.) |
| bulk density | 560kg/m3 |
| density | 1.114 g/mL at 25 °C (lit.) |
| vapor pressure | 0.003 hPa (20 °C) |
| refractive index | 1.6703 |
| Fp | >230 °F |
| storage temp. | Store below +30°C. |
| solubility | 1.7g/l |
| pka | 3.92(at 25℃) |
| form | flakes |
| color | light tan to purple |
| Odor | Ammonia odor |
| PH | 7.1 (1g/l, H2O, 20℃) |
| PH Range | Non& uorescence (3.4) to blue & uorescence (4.8) |
| Water Solubility | Insoluble. 0.1698 g/100 mL |
| Merck | 14,6398 |
| BRN | 386133 |
| Henry's Law Constant | 6.13 x 10-10 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| Exposure limits | TLV-TWA not assigned; carcinogenicity:Human Carcinogen (skin) (MSHA andOSHA). |
| Major Application | color filter, photoresists, recording media, light-emitting device, disk, display device, oil products, construction materials, leather, textile, chalk, explosives |
| InChI | 1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2 |
| InChIKey | RUFPHBVGCFYCNW-UHFFFAOYSA-N |
| SMILES | Nc1cccc2ccccc12 |
| CAS DataBase Reference | 134-32-7(CAS DataBase Reference) |
| IARC | 3 (Vol. 4, Sup 7) 1987 |
| NIST Chemistry Reference | 1-Naphthalenamine(134-32-7) |
| EPA Substance Registry System | 1-Naphthalenamine (134-32-7) |
Safety Information
| Hazard Codes | C,N,Xn,T |
| Risk Statements | 34-51/53-22-45 |
| Safety Statements | 26-36/37/39-45-61-24-53 |
| RIDADR | UN 2790 8/PG 3 |
| WGK Germany | 2 |
| RTECS | QM1400000 |
| F | 8-23 |
| Autoignition Temperature | 460 °C |
| TSCA | TSCA listed |
| HS Code | 2921 45 00 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 2 Carc. 1A |
| Hazardous Substances Data | 134-32-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 680 mg/kg |
| Chemical Properties | α-Naphthylamine exists as white needle-like crystals which turn red on exposure to air. Has a weak ammonia-like odor. Solubility in water is 0.16% at 20℃. It behaves as a typical primary aromatic amine in forming salts with strong acids (but not with acetic or benzoic acid) and readily forming N-acyl derivatives. 1-Naphthylamine couples with diazo compounds in the 4-position, with up to 10 % byproduct being formed by coupling in the 2-position. |
| Physical properties | White to yellow crystals or rhombic needles with an unpleasant odor. Becomes purplish-red on exposure to air. Odor threshold concentrations were 140–290 μg/m3 (quoted, Keith and Walters, 1992). |
| Uses | 1-Naphthylamine is used as a chemical intermediate in the synthesis of a wide variety of chemicals, the most important of which include dyes, tonic prints, Toning prints made with cerium salts, antioxidants, and herbicides. |
| Preparation | 1-Naphthylamine is prepared by reduction of 1-nitronaphthalene: Purified 1-nitronaphthalene was traditionally reduced with iron in boiling dilute hydrochloric acid, but modern plants use hydrogenation with a nickel catalyst. The 1-naphthylamine produced is further purified by distillation under vacuum. The content of 2-naphthylamine in the commercial product is specified at <10 ppm. |
| Application | 1-Naphthylamine is mainly used for the production of 1-naphthol. Other major uses are in the production of aminonaphthalenesulfonic acid dye intermediates and as a component of azo dyes. 1-Naphthylamine can also be used as a starting material to synthesize: [(S)-HY-Phos], a novel chiral phosphine-phosphoramidite ligand for use in rhodium-catalyzed asymmetric hydrogenation of various functionalized olefins. N-(naphthalen-1-yl)picolinamide. Pitnot-2, an inactive analog of clathrin inhibitor Pitstop 2. |
| Definition | ChEBI: 1-naphthylamine is a naphthylamine that is naphthalene substituted by an amino group at position 1. It has a role as a human xenobiotic metabolite. |
| Synthesis Reference(s) | Tetrahedron Letters, 25, p. 429, 1984 DOI: 10.1016/S0040-4039(00)99903-9 Chemical and Pharmaceutical Bulletin, 34, p. 1524, 1986 DOI: 10.1248/cpb.34.1524 |
| General Description | 1-naphthylamine appears as a crystalline solid or a solid dissolved in a liquid. Insoluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals. |
| Air & Water Reactions | Sensitive to exposure to air and light. Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105]. |
| Reactivity Profile | 1-Aminonaphthalene is incompatible with oxidizing agents. 1-Aminonaphthalene is also incompatible with nitrous acid. 1-Aminonaphthalene reduces warm ammoniacal silver nitrate. . |
| Hazard | Toxic, especially if containing the β isomer;a questionable carcinogen. |
| Health Hazard | 1-Naphthylamine is a moderately toxic and cancer-causing substance. The toxic symptoms arising from oral intake or skin absorption of this compound include acute hemorrhagic cystitis, dyspnea, ataxia, dysuria, and hematuria. An intraperitoneal LD50 value in mice is 96 mg/kg. Inhalation of dusts or vapors is hazardous, showing similar symptoms. 1-Naphthylamine caused leukemia in rats. There is substantial evidence of its cancer-causing effects in animals and humans. |
| Fire Hazard | Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire. |
| Safety Profile | Confirmed carcinogenwith experimental tumorigenic data. Alongwith p-naphthylamine and benzidine, it hasbeen incriminated as a cause of urinarybladder cancer. Poison by subcutaneous andintraperitoneal routes. Moderately toxic byingestion. Mutation data reported.Combustible when exposed to heat orflame. Incompatible with nitrous acid. Tofight fire, use dry chemical, CO2, mist, spray.When heated to decomposition it emitstoxic fumes of NOx. |
| Potential Exposure | α-Naphthylamine is used as an intermediatein dye production; for manufacturing herbicidesand antioxidants; in the manufacture of condensationcolors, rubber, and in the synthesis of many chemicals,such as α-naphthol, sodium naphthionate; o-naphthionicacid; Neville and Winther’s acid; sulfonated naphthylamines,α-naphthylthiourea (a rodenticide); and N-phenyl-α-naphthylamine. |
| Carcinogenicity | 1-Naphthylamine has been tested for carcinogenic activityin mice, hamsters, and dogs by oral administration, innewborn mice by SC injection, and in mice by bladderimplantation. Most of these studies reportednegative findings, while a few found marginal or equivocalresults. In contrast, with the exception of bladder implantationstudy, 2-naphthylamine gave positive results in virtuallyall these studies. Mixed results were reported in variousgenotoxicity tests. 1-Naphthylamine was positive in theAmes test and in vitro chromosome aberration, negative inmicronucleus, cell transformation, and recessive lethal mutationin Drosophila, and inconclusive in sister chromatidexchange assays. |
| Environmental fate | Biological. 1-Naphthylamine added to three different soils was incubated in the dark at 23 °Cunder a carbon dioxide-free atmosphere. After 308 d, 16.6 to 30.7% of the 1-naphthylamine addedto soil biodegraded to carbon dioxide (Graveel et al., 1986). Li and Lee (1999) investigated thereaction of 10 mL of 7 mM 1-naphthylamine with 4 g of a Chalmers soil (pH: 6.5, 11.1% sand,72.8% silt, 16.0% clay). After 120 h, the soil was washed with acetonitrile and the extractantanalyzed using GC/MS. The primary transformation product was a dimer tentatively identified asN-(4-aminonaphthyl)-1-naphthylamine. The investigators hypothesized that the formation of thiscompound and two other unidentified dimers was catalyzed by minerals present in the soil. Heukelekian and Rand (1955) reported a 5-d BOD value of 0.89 g/g which is 34.6% of theThOD value of 2.57 g/g. In activated sludge inoculum, following a 20-d adaptation period, nodegradation was observed (Pitter, 1976). Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary aminesolutions by UV light in the presence of titanium dioxide resulted in the formation of ammoniumand nitrate ions. Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 1-naphthylamine andother substituted aromatic hydrocarbons (aniline, toluidine, 2-naphthylamine, phenol, cresol,pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence ofammonium ion. They reported that the aromatic ring was not chlorinated as expected but wascleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride that formedincreased as the pH was lowered (Kanno et al., 1982). At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacitieswere 250, 140, 79, and 44 mg/g, respectively. At pHs 7.0 and 9.0, the GAC adsorption capacitieswere 360, 160, 75, and 34 mg/g at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L,respectively (Dobbs and Cohen, 1980). |
| Shipping | UN2077 alpha-Naphthylamine, Hazard Class:6.1; Labels: 6.1-Poisonous materials. PGIII. |
| Purification Methods | Sublime the amine at 120o in a stream of nitrogen, then crystallise it from pet ether (b 60-80o), or absolute EtOH then diethyl ether. Dry it in vacuo in an Abderhalden pistol. It has also been purified by crystallisation of its hydrochloride (see below) from water, followed by liberation of the free base and distillation; it is finally purified by zone melting. The styphnate has m 181-182o (from EtOH). [Beilstein 12 III 2846, 12 IV 3009.] CARCINOGEN. |
| 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, nitrous acid, organicanhydrides, isocyanates, aldehydes. Oxidizes on contactwith air. |
| Waste Disposal | Controlled incinerationwhereby oxides of nitrogen are removed from the effluentgas by scrubber, catalyst, or thermal device. Consult withenvironmental regulatory agencies for guidance onacceptable disposal practices. Generators of waste containingthis contaminant (≥100 kg/mo) must conform withEPA regulations governing storage, transportation, treatment,and waste disposal. |
1-Naphthylamine Preparation Products And Raw materials
| Raw materials | Hydroxylamine hydrochloride-->Polyphosphoric acid-->Sodium sulfide-->Naphthalene-->Sodium sulfide nonahydrate-->1-Naphthoic acid-->1-Nitronaphthalene |
| Preparation Products | 1-Naphthol-->ACID BLACK 24-->ACID BLUE 113-->Direct Blue 71-->2-Methoxynaphthalene-->ACID BLUE 120-->7,8-BENZOQUINOLINE-->1-Chloronaphthalene-->1-(1-NAPHTHYL)-2-THIOUREA-->1,4-DICHLORONAPHTHALENE-->Direct Black 103-->1-AMINO-8-NAPHTHOIC ACID-->1-Naphthyl isocyanate-->3-Hydroxy-N-naphthalen-1-ylnaphthalene-2-carboxamide-->5-ACETAMIDONAPHTHALENE-1-SULFONYL CHLORIDE-->N-Phenyl-1-naphthylamine-->Acid Black 26-->Acid Orange 116-->N-(1-NAPHTHYL)-3-AMINOPROPANESULFONIC ACID SODIUM SALT-->γ-L-glutamyl-1-naphthylamide-->Reactive Disperse Scarlet G-->Tracid Rubine 5bl-->Direct Black 80-->Acid Brown 14-->Direct Blue 78-->DISPERSE BLACK 1-->4-PHENYLAZO-1-NAPHTHYLAMINE-->C.I. Direct blue 70-->Solvent Black 3 |
