1-나프톨

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Danger

• 유해·위험 문구

  H302：삼키면 유해함

  H311：피부와 접촉하면 유독함

  H315：피부에 자극을 일으킴

  H317：알레르기성 피부 반응을 일으킬 수 있음

  H318：눈에 심한 손상을 일으킴

  H335：호흡 자극성을 일으킬 수 있음

  H371：장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재)

  H410：장기적 영향에 의해 수생생물에 매우 유독함

• 예방조치문구

  P273：환경으로 배출하지 마시오.

  P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

  P301+P312：삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.

  P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

1-나프톨 MSDS

• Oxidation base 33

1-나프톨 화학적 특성, 용도, 생산

• 개요

  1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
  α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant.

• 화학적 성질

  Pale grey to brown solid with an unpleasant phenol odour. Darkens in the presence of light. Evaporates with water vapour. Soluble in ethanol, ether, benzene, chloroform and alkali solutions, insoluble in water. Precipitates violet when exposed to ferric chloride. 1-Naphthol [90-15-3] a-naphthol, 1- naphthalenol, 1-hydroxynaphthalene, C10H8O, Mr 144.16, forms colorless prisms (from toluene) which darken on exposure to air or light. The compound is steam volatile and sublimable. 1-Naphthol is reduced by sodium in liquid ammonia to give 5,6,7,8-tetrahydro-1-naphthol and is oxidized by NaOCl – FeCl3 or I2–KI to give a violet color. It is chlorinated by phosphorus pentachloride at 150℃ to give 1-chloronaphthalene, by sulfuryl chloride to give 4- chloro-1-naphthol, or by Cl2–CH3COOH to give 2,4-dichloro-1-naphthol. Similarly bromine forms 2,4-dibromo-1-naphthol, and this reaction may be used quantitatively for titration. Nitration of 1-naphthol gives complex mixtures. The crude 2,4-dinitro derivative was used in the mid-1800s as an acid yellow dye comparable to picric acid. Sulfonation at 50℃ readily yields 1-naphthol-2,4-disulfonic acid. Nitrous acid gives mainly the 2-nitroso derivative, contaminated with the 4-nitroso isomer.

• 용도

  1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.

• 제조 방법

  2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
  Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%.

• 정의

  ChEBI: 1-naphthol is a naphthol carrying a hydroxy group at position 1. It has a role as a genotoxin and a human xenobiotic metabolite.

• 주요 응용

  1-Naphthol is a hydroxyl-aromatic compound. It has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.

• 일반 설명

  1-Naphthol, a metabolite of carbaryl and naphthanlene. It is formed by spontaneous reaction from (1R, 2S)-Naphthalene epoxide followed to form 1, 4-Dihydroxynaphthalene.

• 위험도

  Toxic by ingestion and skin absorption.

• 색상 색인 번호

  1-Naphthol can be used in dye manufacture and is classified as a hair dye. Combined with epichlorhydrin and NaOH to form alpha-naphthyl glycidyl ether, it caused sensitization in one of three workers in a chemical plant.

• Safety Profile

  Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. An experimental teratogen. Experimental reproductive effects. A severe eye and skin irritant. Mutation data reported. Ingestion of large amounts can cause nephritis, vomiting, diarrhea, circulatory collapse, anemia, convulsions, and death. Can cause kidney irritation and injury to cornea and lens of the eye. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

• Synthesis

  To a 10 mL pressure vessel, aryl halide (1.00 mmol), copper (I) oxide (0.05 mol), ligand (0.05 mol), 3 M sodium hydroxide (2 mL), and organic solvent (2 mL) were added. The reaction mixture was irradiated at 160 °C for 10 min with strong stirring. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a plug of celite in a fritted filter funnel and washed with ethyl acetate. The product was extracted using 30 mL of ethyl acetate for three times. The organic extract is washed three times with 10 mL water and two times with 10 mL of brine. The combined organic phases were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to afford 1-naphthol.

• Purification Methods

  Sublime 1-naphthol, then crystallise it from aqueous MeOH (charcoal), aqueous 25% or 50% EtOH, *C6H6, cyclohexane, heptane, CCl4 or H2O. Dry it over P2O5 in vacuo. The 4-nitrobenzoate has m 143o (from EtOH). [Shizuka et al. J Am Chem Soc 107 7816 1985, Beilstein 8 H 596, 6 IV 4208.]

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