1-ナフチルアミン
1-ナフチルアミン溶液 (スプレー用) (受注時調製品) · (1-ナフチル)アミン · ファーストガーネットベースB · アゾイックDC114 · ナフタリジン · C.I.アゾイックジアゾコンポーネント114 · 1-アミノナフタリン · 1-アミノナフタレン
識別子と物理属性
| CAS No. | 134-32-7 |
|---|---|
| 分子式 | C10H9N |
| 平均分子量 | 143.18 g/mol |
| 単同位体質量 | 143.07349929 g/mol |
| SMILES | Nc1cccc2ccccc12 |
| InChIKey | RUFPHBVGCFYCNW-UHFFFAOYSA-N |
| PubChem CID | 8640 |
| ChEMBL | CHEMBL57394 |
| ChEBI | CHEBI:50450 |
| EC No. | 205-138-7 |
| DTXSID | DTXSID7020920 |
| 現地名 | 1-ナフチルアミン |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 極性表面積 | 26 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 133 |
| pH | Weak base7.1 (1g/l, H2O, 20℃) |
| LogP（分配係数） | log Kow = 2.25 |
| 臭い | Ammonia-like odor.アンモニア臭 |
| 密度 | 1.12 at 77 °F (USCG, 1999) - Denser than waterwill sink1.114 g/cu cm1.12 g/cm³1.0228 @ 20°C1.114 g/mL at 25 °C (lit.) |
| Color/Form | Needles from ethanol (aq) or etherYELLOW RHOMBIC NEEDLESWhite crystals becoming red on exposure to airNeedles, becoming red on exposure to air, or a reddish, crystal massColorless crystalsdarkens in air to a reddish-purple color |
| 溶解度 | less than 1 mg/mL at 66 °F (NTP, 1992)Crystal powderbecomes bluish on exposure to air and light. Sol in about 27 parts watersol in alcohol and ether /Hydrochloride/Sol in chloroformFreely sol in alcohol and etherIn water, 1.7X10+3 mg/L @ 20 °CSolubility in water: none1.7g/リットル不溶性。 0.1698g/100mL |
| 引火点 | 315 °F (NTP, 1992)157 °C157 °C, 315 °F, (closed cup)157 °C c.c.>230 °F |
| 沸点 | 574 °F at 760 mmHg (NTP, 1992)300.7 °C300.8 °C573 °F300.7 °C @760 [mm Hg]301 °C (lit.) |
| Decomposition | The substance decomposes on burning producing nitrogen oxides and carbon monoxide. |
| 融点 | 122 °F (NTP, 1992)49.2 °C50.0 °C47-50 °C (lit.) |
| 蒸気密度 | 4.93 (NTP, 1992) - Heavier than airwill sink (Relative to Air)4.93 (Air= 1)Relative vapor density (air = 1): 4.93 |
| 蒸気圧 | 1 mmHg at 219.7 °F5 mmHg at 279.9 °F (NTP, 1992)0.00418 [mmHg]4.18X10-3 mm Hg @ 25 °C /Extrapolated/Vapor pressure, Pa at 20 °C: 0.531 mmHg at 220 °F(220 °F): 1 mmHg0.003 hPa (20 °C) |
| 屈折率 | 1.6703 |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 3.92(at 25℃) |
| 外観・状態 | フレーク |
| 色 | 薄い黄褐色から紫色 |
| Merck | 14,6398 |
| BRN | 386133 |
| ヘンリー定数 | 6.13 x 10-10 atmm3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| 主な用途 | カラーフィルター、フォトレジスト、記録媒体、発光ダイオード、ディスク、表示装置、石油製品、建築材料、皮革、繊維、チョーク、爆発物 |
| 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 データベース | 134-32-7(CAS DataBase Reference) |
| NISTの化学物質情報 | 1-Naphthalenamine(134-32-7) |
| EPAの化学物質情報 | 1-Naphthalenamine (134-32-7) |
化学的特性
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.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)Danger |
|---|---|
| 規制情報 | Chemical: 1-NaphthalenamineHazard Traits - CarcinogenicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the productStatus: Cease Manufacture Update: 04-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1659Status: Active Update: 25-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/203911-Naphthalenamine: HSNO Approval: HSR001523 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | IMAP assessments - 1-Naphthalenamine: Environment tier I assessmentIMAP assessments - 1-Naphthalenamine: Human health tier I assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire. (USCG, 1999)· Combustible material: may burn but does not ignite readily.· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.· Corrosives in 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.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | Inhalation may cause cyanosis (blue color in lips and under finger nails). Contact with liquid causes local irritation of eyes. Neither ingestion nor contact with skin produces any recognized immediate effects. (USCG, 1999) |
用途
解説
ナフタレンにアミノ基が置換した塩基性化合物，C10H7NH2．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体がある．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体はニトロ化合物の還元でつくられるが，β体は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体は発がん性のため製造と使用が禁止され，β体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、有機合成
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.
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.
製法・合成法
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.
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.