1-ナフチルアミン 化學(xué)特性,用途語,生産方法
外観
白色～うすい黃色～うすい赤色粉末～結(jié)晶
解説
ナフタレンにアミノ基が置換した塩基性化合物，C
10H
7NH
2．アミノ基の位置により1-ナフチルアミンおよび2-ナフチルアミンの異性體がある．一般には，α-およびβ-ナフチルアミンとよばれることが多い．α體はニトロ化合物の還元でつくられるが，β體はβ-ナフトールとアンモニアの反応でつくられる．染料などの中間物．β體は発がん性のため製造と使用が禁止され，β體からの中間物合成は，別経路でつくられるようになった．
用途
Αーナフトール?Αーナフチルアミンスルホン酸塩?アゾ系染料、媒染剤、ゴム薬品、有機(jī)合成
化學(xué)的特性
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.
物理的性質(zhì)
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).
使用
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.
主な応用
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.
製造方法
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.
定義
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.
一般的な説明
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.
空気と水の反応
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].
反応プロフィール
1-Aminonaphthalene is incompatible with oxidizing agents. 1-Aminonaphthalene is also incompatible with nitrous acid. 1-Aminonaphthalene reduces warm ammoniacal silver nitrate. .
危険性
Toxic, especially if containing the β isomer;
a questionable carcinogen.
健康ハザード
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.
火災(zāi)危険
Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire.
安全性プロファイル
Confirmed carcinogen
with experimental tumorigenic data. Along
with p-naphthylamine and benzidine, it has
been incriminated as a cause of urinary
bladder cancer. Poison by subcutaneous and
intraperitoneal routes. Moderately toxic by
ingestion. Mutation data reported.
Combustible when exposed to heat or
flame. Incompatible with nitrous acid. To
fight fire, use dry chemical, CO2, mist, spray.
When heated to decomposition it emits
toxic fumes of NOx.
職業(yè)ばく露
α-Naphthylamine is used as an intermediate
in dye production; for manufacturing herbicides
and antioxidants; in the manufacture of condensation
colors, rubber, and in the synthesis of many chemicals,
such as α-naphthol, sodium naphthionate; o-naphthionic
acid; Neville and Winther’s acid; sulfonated naphthylamines,
α-naphthylthiourea (a rodenticide); and N-phenyl-
α-naphthylamine.
発がん性
1-Naphthylamine has been tested for carcinogenic activity
in mice, hamsters, and dogs by oral administration, in
newborn mice by SC injection, and in mice by bladder
implantation. Most of these studies reported
negative findings, while a few found marginal or equivocal
results. In contrast, with the exception of bladder implantation
study, 2-naphthylamine gave positive results in virtually
all these studies. Mixed results were reported in various
genotoxicity tests. 1-Naphthylamine was positive in the
Ames test and in vitro chromosome aberration, negative in
micronucleus, cell transformation, and recessive lethal mutation
in Drosophila, and inconclusive in sister chromatid
exchange assays.
輸送方法
UN2077 alpha-Naphthylamine, Hazard Class:
6.1; Labels: 6.1-Poisonous materials. PGIII.
純化方法
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.
不和合性
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, organic
anhydrides, isocyanates, aldehydes. Oxidizes on contact
with air.
廃棄物の処理
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.
1-ナフチルアミン 上流と下流の製品情報(bào)
原材料
準(zhǔn)備製品