1,5-ジヒドロキシナフタレン
1,5-ジヒドロキシナフタレン · 1,5-ナフタレンジオール · 1,5-ジヒドロキシナフタリン · デュラフルデベロッパーE · ズラフルデベロッパーE · ナフタレン-1,5-ジオール · オキシデーションベース · 1，5ジヒドロキシナフタレン
識別子と物理属性
| CAS No. | 83-56-7 |
|---|---|
| 分子式 | C10H8O2 |
| 平均分子量 | 160.17 g/mol |
| 単同位体質量 | 160.0524295 g/mol |
| SMILES | Oc1cccc2c(O)cccc12 |
| InChIKey | BOKGTLAJQHTOKE-UHFFFAOYSA-N |
| PubChem CID | 6749 |
| ChEMBL | CHEMBL204658 |
| EC No. | 201-487-4 |
| DTXSID | DTXSID2052574 |
| 現地名 | 1,5-ジヒドロキシナフタレン |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 40.5 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 140 |
| 物質分類 | Other Classes -> Naphthols |
| 化粧品 | Hair dyeing |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | 1.82 |
| 溶解度 | Solubility in water, g/100ml at 20 °C: 0.060.6g/リットル水に溶ける。 |
| 引火点 | 252 °C252 °C c.c.252°C |
| Decomposition | 250 °C |
| 蒸気圧 | 0.00000715 [mmHg]0-0Pa at 25℃ |
| Physical Description | Orange powder[ICSC]ORANGE POWDER. |
| Collision Cross Section | 131.0 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID2052574]134.35 Ų [M-H]- [CCS Type: DTMethod: stepped-field]133.2 Ų [M-H]- |
| 融点 | 259-261 °C (dec.) (lit.) |
| 沸点 | 246.06°C (rough estimate) |
| 密度 | 1.0924 (rough estimate) |
| 屈折率 | 1.5418 (estimate) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| pKa（酸解離定数） | 9.28±0.40(Predicted) |
| 外観・状態 | 個体 |
| 色 | ペールベージュからベリーダークブラウン |
| pH | 6 (0.5g/l, H2O, 20℃) |
| BRN | 2044951 |
| 化粧品成分の機能 | ヘアカラーリング |
| InChI | 1S/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H |
| InChIKey | BOKGTLAJQHTOKE-UHFFFAOYSA-N |
| SMILES | Oc1cccc2c(O)cccc12 |
| LogP（分配係数） | 1.7-1.82 at 23℃ |
| CAS データベース | 83-56-7(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,5-Naphthalenediol(83-56-7) |
| EPAの化学物質情報 | 1,5-Naphthalenediol (83-56-7) |
化学的特性
Grey powder 1,5-Naphthalenediol [83-56-7], 1,5-dihydroxynaphthalene, Azurol, C10H8O2, Mr 160.16, forms colorless needles (from aqueous methyl cellosolve). The compound is sublimable, readily soluble in ether and acetone, but only sparingly soluble in water and hydrocarbons. It is oxidized to 5-hydroxy-1,4-naphthoquinone ( juglone) by CrO3. Amination gives 1,5-naphthalenediamine; coupling with diazotized anilines occurs in the 2- or 4-position.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.7% (1 of 153) of reports.WarningH302 (77.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 153 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 1,5-NaphthalenediolStatus: Active Update: 25-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/273201,5-Naphthalenediol: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - 1,5-Naphthalenediol: Human health tier II assessment |
| 火災危険 | Combustible. |
| 有害性の概要 | A mild eye irritant[ICSC] A skin and eye irritantMay be harmful if ingested[MSDSonline] See 1-Napththol and 2-Naphthol. See 2,7-Naphthalenediol. |
| Chemical Dangers | On combustion, forms toxic fumes. Reacts with strong oxidants. |
| Hazard Classes and Categories | Acute Tox. 4 (77.8%)Acute toxicity - category 4 |
| 消火 | Use water spray, powder. |
| 応急処置措置 | Fresh air, rest.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| 安全保管 | Separated from strong oxidants. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use local exhaust or breathing protection. |
| Effects of Short Term Exposure | The substance is mildly irritating to the eyes. |
| 暴露経路 | The substance can be absorbed into the body by ingestion. |
| Signs and Symptoms | Redness. |
| F | 8-21 |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | QJ4740000 |
| 税関コード | 29072900 |
| 危険文句（R） | 22-51/53-36-36/37/38 |
| 化審法 | (4)-356 |
| 危険表示 | Xn,N,Xi |
| 安全措置（S） | 22-24/25-61-39-29-26 |
| 危険等級 | Aquatic Chronic 2Eye Irrit. 2Skin Sens. 1B |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
黒色の触染アゾ染料中間体。
使用
1,5-Dihydroxynaphthalene is an intermediate of synthetic mordant azo dyes. It is an intermediate used in organic synthesis, pharmaceuticals, dyestuff fields and photograph industry. It is used as a coupling component in azo dyes as exemplified in the metallizable (Cr) wool dye, C.I. Mordant Black 9.
製法・合成法
純化方法
The diol (~30g) is purified by making into a thick paste with H2O and suspending this in 3L of H2O containing 200mL of EtOH, boiling under reflux for 3hours, cooling to 30o, saturating with SO2, digesting below the boiling point for 1hour and filtering fast through a large hot filter paper. The hot filtrate is poured onto crushed ice whereby the diol (15-20g) separates as colourless needles (m 258o) [Wheeler & Ergle J Am Chem Soc 52 4873 1930]. Recrystallise it from H2O or nitromethane under N2 to avoid oxidation. The dibenzoyl derivative has m 245o (from EtOH). The 5-methoxy-1-naphthol derivative [prepared from the diol in MeOH/HCl (1:30 weight to volume ratio) and set aside at 25o for 9-10days] crystallised from pet ether (m 135-136o) or from CH2Cl2/hexane (needles m 140o) [Bell & McCaffrey Aust J Chem 46 731 1993]. [Beilstein 6 I 477, 6 II 950, 6 III 5265, 6 IV 6554.]