4-(ベンジルオキシ)フェノール
4-(ベンジルオキシ)フェノール · p-(ベンジルオキシ)フェノール · 4-フェニルメチルヒドロキノン · モノベンゾン · 4-(フェニルメトキシ)フェノール · ベノキン · ヒドロキノンモノベンジルエーテル · アルバ
識別子と物理属性
| CAS No. | 103-16-2 |
|---|---|
| 分子式 | C13H12O2 |
| 平均分子量 | 200.23 g/mol |
| 単同位体質量 | 200.08372962 g/mol |
| SMILES | Oc1ccc(OCc2ccccc2)cc1 |
| InChIKey | VYQNWZOUAUKGHI-UHFFFAOYSA-N |
| PubChem CID | 7638 |
| ChEMBL | CHEMBL1388 |
| ChEBI | CHEBI:34380 |
| EC No. | 203-083-3 |
| DTXSID | DTXSID2020717 |
| 現地名 | 4-(ベンジルオキシ)フェノール |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 極性表面積 | 29.5 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 167 |
| 物質分類 | Other Classes -> Other Aromatic Compounds |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical diffusion |
| LogP（分配係数） | 3.2 |
| 臭い | ODORLESS |
| 密度 | 1.261,26 g/cm3 |
| Color/Form | LUSTROUS LEAFLETS FROM WATERWHITE CRYSTALLINE POWDER |
| 溶解度 | SOLUBILITY IN BOILNG WATER ABOUT 1.0 G/100 MLSOL IN ALC, ETHER, BENZENEINSOL IN WATERFREELY SOL IN ACETONEPractically insoluble in petroleum hydrocarbons, very soluble in benzene and alkalies.3.92e-02 g/Lクロロホルム（微量）、DMSO（微量）、メタノール（微量）わずかに溶ける |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 融点 | 122.5 °C110 - 118 °C119-120 °C (lit.) |
| 蒸気圧 | 0.0000225 [mmHg] |
| 沸点 | 297.96°C (rough estimate) |
| 屈折率 | 1.5906 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 10.29±0.15(Predicted) |
| 外観・状態 | パウダー、クリスタル、および/またはチャンク |
| 色 | オフホワイトからベージュ、ブラウン |
| 由来生物 | rabbit |
| Merck | 14,6248 |
| BRN | 1958305 |
| InChI | 1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2 |
| InChIKey | VYQNWZOUAUKGHI-UHFFFAOYSA-N |
| SMILES | Oc1ccc(OCc2ccccc2)cc1 |
| LogP（分配係数） | 2.651 (est) |
| CAS データベース | 103-16-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Monobenzone(103-16-2) |
| EPAの化学物質情報 | Monobenzone (103-16-2) |
化学的特性
4-Benzyloxyphenol is a cream to beige-light brownish crystals classified as a hydroquinone monobenzyl ether. It is soluble in alcohol, benzene and ether, and almost insoluble in water. 4-Benzyloxyphenol is a depigmenting agent that has the effect of enhancing the rate of elimination of melanin secreted by skin cells, and studies have shown that the molecular mechanism of its action may be related to tyrosinase.
安全性と法規制
| GHS 分類 | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 規制情報 | Chemical: Phenol, 4-(phenylmethoxy)- |
| 有害性の概要 | A tumorigen and mild skin irritantIntraperitoneal LD50 (rat) = 4500 mg/kg[RTECS] Emergency treatment: symptomatic chemical dermal exposureReported skin sensitizer in the rubber industry[HSDB] An eye irritantMay cause skin sensitization[ESIS] A strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Sens. 1 (100%)Eye irritation - category 2Eye Irrit. 2 |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Human Toxicity Excerpts | UNTOWARD EFFECTS, INCL MILD ERYTHEMA, DERMATITIS, & ECZEMATOUS REACTIONS, HAVE BEEN REPORTED. ... SYSTEMIC TOXICITY HAS NOT BEEN OBSERVED AFTER ITS LOCAL APPLICATION.SUMMARY TOXICITY STATEMENT: ACUTE... LOW... LOW= CAUSES READILY REVERSIBLE TISSUE CHANGES WHICH DISAPPEAR AFTER EXPOSURE STOPSCAUSES SOME DISCOMFORT.... Many cases of dermatitis and leucoderma that were evidently caused by skin contact with rubber that contained hydroquinone monobenzyl ether as an antioxidant /have been reported/. |
| Non-Human Toxicity Excerpts | ... No toxic changes were observed in guinea pigs ingesting this compound at the level of 160 mg/kg daily for 2 months for a total dose of 4.37 g. The only change noted was a depigmentation of the hair. |
用途
用途
ゴム抗酸化剤,安定剤、重合禁止剤、化学品中間体
用途
有機合成原料。
説明
4-(Benzyloxy)phenol, also called monobenzone and monobenzyl ether of hydroquinone (MBEH) is an organic chemical in the phenol family with chemical formula C6H5CH2OC6H4OH. It is used as a topical drug for medical depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water.The topical application of monobenzone in animals, increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans.
使用
4-Benzyloxyphenol is used in the synthesis of bis(4-benzyloxyphenoxy)phenyl phosphine oxide. It plays an essential role in the preparation of hetaryl-azophenol dyes via heterocyclic amines in nitrosyl sulphuric acid. It is also used for polyester fiber dyeing and in rubber industry. It acts as a depigmenting agent.
製法・合成法
製造方法
4-Benzyloxyphenol Synthesis: Add 2.63g (0.028mol) of hydroquinone to a 100mL conical flask, weigh 1.12g (0.028mol) of sodium hydroxide, add 8mL of water, wait for the sodium hydroxide to dissolve and add dropwise to the conical flask with hydroquinone, shake well, then add 15mL of DMF and 2.52g (0.02mol) of benzyl chloride, under microwave radiation power of 320W The reaction was cooled to room temperature at the end of the reaction. The reaction was first adjusted to alkalinity with 10% sodium hydroxide, filtered, and the filtrate was washed with 10% sodium hydroxide until the filtrate was colorless (the filtrate was hydroquinone bis(benzyl ether), which could be recycled). The filtrate was acidified with hydrochloric acid to make Monobenzone completely precipitated, and then washed by filtration and ice water, recrystallized with alcohol and water, and decolorized by activated carbon to obtain 2.55g of white solid, the yield was 63.79%.
純化方法
Crystallise it from EtOH or H2O, and dry (P2O5) under vacuum. [Walter et al. J Am Chem Soc 108 5210 1986, Beilstein 6 IV 5778.]