o-クレゾール
o-クレゾール · o-トルオール · o-メチルフェノール · 2-メチルフェノール · o-クレシル酸 · o-ヒドロキシトルエン · o-クレソール · oクレゾ-ル
識別子と物理属性
| CAS No. | 95-48-7 |
|---|---|
| 分子式 | C7H8O |
| 平均分子量 | 108.14 g/mol |
| 単同位体質量 | 108.05751487 g/mol |
| SMILES | Cc1ccccc1O |
| InChIKey | QWVGKYWNOKOFNN-UHFFFAOYSA-N |
| PubChem CID | 335 |
| ChEMBL | CHEMBL46931 |
| ChEBI | CHEBI:28054 |
| EC No. | 202-423-8 |
| DTXSID | DTXSID8021808 |
| 現地名 | o-クレゾール |
化学・物理的性質
| XLogP | 2 |
|---|---|
| 極性表面積 | 20.2 |
| 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 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 70 |
| 融点 | 29-31 °C (lit.) |
| 沸点 | 191 °C (lit.) |
| 密度 | 1.048 g/mL at 25 °C |
| 蒸気密度 | 3.72 (vs air) |
| 蒸気圧 | 0.3 mm Hg ( 20 °C) |
| 屈折率 | 1.5361 |
| FEMA | 3480 | O-CRESOL |
| 引火点 | 178 °F |
| 貯蔵条件 | under inert gas |
| 溶解度 | 20g/リットル20g/L(20℃) |
| 外観・状態 | 液体または低融点固体 |
| pKa（酸解離定数） | 10.2(at 25℃) |
| 色 | 白から茶色 |
| pH | 4.8 (20g/l, H2O, 20℃) |
| 臭い | ジプロピレングリコール中0.01%。かび臭いフェノールプラスチック 薬草のような 革のような |
| においのタイプ | フェノール系 |
| 臭気閾値 | 0.00028ppm |
| 由来生物 | synthetic |
| 爆発限界 | 1.47%, 148°F |
| 比熱容量 | Cp(crystal): 1.43 J/(g·K), at 25℃ |
| JECFA Number | 691 |
| Merck | 14,2579 |
| BRN | 506917 |
| ヘンリー定数 | 0.34 at 5.25 °C, 0.61 at 10.00 °C, 1.57 at 20.00 °C, 2.33 at 25.00 °C (dynamic equilibrium system- GC, Feigenbrugel et al., 2004a) |
| 誘電率 | 5.8(-5℃) |
| 安定性 | 安定していますが、光と空気に敏感です。可燃性。酸化剤、塩基と相容れない。 |
| 主な用途 | 農業洗浄剤化粧品環境フレーバーそして香料食品および飲料パーソナルケア |
| 化粧品成分の機能 | 抗菌剤香料 |
| InChI | 1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 |
| InChIKey | QWVGKYWNOKOFNN-UHFFFAOYSA-N |
| SMILES | Cc1ccccc1O |
| LogP（分配係数） | 1.95 at 20℃ |
| 表面張力 | 35.86mN/m at 298.15K |
| CAS データベース | 95-48-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Phenol, 2-methyl-(95-48-7) |
| EPAの化学物質情報 | o-Cresol (95-48-7) |
化学的特性
o-Cresol has a musty, phenolic aftertaste.
化学性质
2,6-キシレノールの副産物として得られる。
安全性と法規制
| F | 8-23 |
|---|---|
| 職業暴露区分（OEB） | B |
| 職業暴露限界（OEL） | TWA: 2.3 ppm (10 mg/m3) |
| 水環境危害等級（WGK） | 1 |
| 生命健康即時危険濃度 | 250 ppm |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | GO6300000 |
| 輸送番号（UN） | UN 3455 6.1/PG 2 |
| 毒性 | LD50 orally in rats: 1.35 g/kg (Deichmann, Witherup) |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29071200 |
| 危険文句（R） | 24/25-34-39/23/24/25-23/24/25 |
| 化審法 | (3)-499, (4)-57 優先評価化学物質 |
| 安衛法 | 有機則 第二種有機溶剤等 |
| 危険表示 | T |
| 安全措置（S） | 36/37/39-45-36/37 |
| 危険等級 | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Skin Corr. 1B |
| 包装等級 | II |
| 毒劇物取締法 | 劇物 |
| 自然発火温度 | 555 °C |
| 環境リスク評価 | o-クレゾール(95-48-7) |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 95-48-7(Hazardous Substances Data) |
用途
用途
防腐剤、消毒剤
用途
水質試験用
用途
有機合成原料、溶剤。
天然物の起源
Reported in Acacial farnesiana, ylang-ylang oil (probably as p-cresyl acetate), jasmine absolute, orange oil from leaves, the essence from flowers of Lilium candidum, anise seed oil, the essence of Artemisia santolinoflia, and some sea algae. Also reported found in asparagus, peppermint oil, cheddar cheese, provolone cheese, butter, milk, lean fish, boiled egg, smoked pork, rum, Scotch whiskey, red wine, white wine, coffee and mango.Reported found in cinnamon, coffee, Oriental tobacco, rum, sherry, tea, tomato and whiskey.
使用
o-Cresol is used as a disinfectant and solvent. Lysol disinfectant is a 50% (v/v) mixed-cresol isomer in a soap emulsion formed on mixing with water. Besides disinfection products at solutions of 1–5%, the cresols are used as degreasing compounds, paintbrush cleaners, and additives in lubricating oils. Cresols were previously widely used for disinfection of poultry houses, but this use was discontinued because of their toxicity; they cause respiratory problems and abdominal edema in young chicks. o-Cresol has been used in synthetic resins, explosives, petroleum, photographic, paint, and agricultural industries.
一般的な説明
Colorless or yellow to brown-yellow or pinkish colored liquid with a phenol-like odor. Toxic by ingestion and/or skin absorption. May have a flash point between 100 and 199°F. Causes burns to skin, eyes and mucous membranes. Insoluble in water.
製法・合成法
調製方法
Approximately 60% of o-cresol is obtained from coal-tar and crude oil by using classical techniques such as distillation, stripping, and liquid–liquid extraction. The remaining 40% is obtained synthetically by the alkylation of phenol with methanol. The cresols (cresylic acids) are methyl phenols and generally appear as a mixture of isomers. o-Cresol is a 2-methyl derivative of phenol and is prepared from o-toluic acid or obtained from coal tar or petroleum. Crude cresol is obtained by distilling “gray phenic acid” at a temperature of ≈180–201°C. o-Cresol may be separated from the crude or purified mixture by repeated fractional distillation in vacuo. It can also be prepared synthetically by diazotization of the specific toluidine or by fusion of the corresponding toluenesulfonic acid with sodium hydroxide.
合成方法
フェノールとメタノールを金属酸化物（たとえばAl2O3）触媒存在下で反応させる
純化方法
It can be freed from m-and p-isomers by repeated fractional distillation, It crystallises from *benzene by addition of pet ether. It has been fractionallly crystallised by partial freezing of its melt. The 3,5-dinitrobenzoate (prepared with 3,5-dinitrobenzoyl chloride in dry pyridine, and recrystallised from EtOH or aqueous Me2CO) has m 138o. [Beilstein 6 IV 1940.]