하이드로퀴논모노벤질에터
하이드로퀴논모노벤질에터 · MONOBENZONE · PBP · HYDROQUINONE MONOBENZYL ETHER · Monobenzone powder · 4-BENZYLOXYPHENOL · Benoquin · Monobenzon
식별자 및 물리적 특성
| CAS No. | 103-16-2 |
|---|---|
| 분자식 | C13H12O2 |
| 평균 분자량 | 200.23 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 하이드로퀴논모노벤질에터 |
화학 및 물리적 성질
| XLogP | 3.4 |
|---|---|
| 극성 표면적 | 29.5 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 15 |
| 형식 전하 | 0 |
| 복잡도 | 167 |
| 물질 분류 | Other Classes -> Other Aromatic Compounds |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical diffusion |
| LogP(분배 계수) | 3.2 |
| 냄새 | ODORLESS |
| 밀도 | 1.261,26 g/cm3 |
| Color/Form | LUSTROUS LEAFLETS FROM WATERWHITE CRYSTALLINE POWDER |
| 용해도 | 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/L클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 122.5 °C110 - 118 °C119-120 °C (lit.) |
| 증기압 | 0.0000225 [mmHg] |
| 끓는 점 | 297.96°C (rough estimate) |
| 굴절률 | 1.5906 (estimate) |
| 저장 조건 | Store below +30°C. |
| pKa(산도 계수) | 10.29±0.15(Predicted) |
| 물리적 상태 | 분말, 결정 및/또는 덩어리 |
| 색상 | 미색부터 베이지, 브라운까지 |
| 생물학적 소스 | rabbit |
| 용해도 | 약간 용해됨 |
| 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(분배 계수) | 2.651 (est) |
| NIST | Monobenzone(103-16-2) |
| EPA | Monobenzone (103-16-2) |
화학적 성질
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.
안전 및 규제
| GHS 분류 | 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] |
|---|---|
| 규제 정보 | Chemical: Phenol, 4-(phenylmethoxy)- |
| 유해성 요약 | 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 |
| 처리 방법 | 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. |
| 유해 작용 | 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.... No toxic changes were observed in mice that were injected ip with 600 mg/kg of hydroquinone monobenzyl ether daily for 3 weeks.... A 5 percent concentration of hydroquinone monobenzyl ether in ethanol ... was nonsensitizing /to guinea pigs/. |
| Probable Routes of Human Exposure | IN RUBBER INDUSTRY, NUMBER OF CHEMICAL AGENTS USED IN PREPARING RUBBER CAN SENSITIZE EXPOSED WORKERS. THESE INCL...ANTIOXIDANT, MONOBENZYL ETHER OF HYDROQUINONE... |
| Non-Human Toxicity Values | LD50 Rat oral >3.2 g/kg /Hydroquinone monobenzyl ether (Sodium salt/ |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | SJ7700000 |
| 독성 | LD50 i.p. in mice: >600 mg/kg (Takahashi) |
| 관세 코드 | 29095090 |
| 위험 문구(R) | 36-43 |
| 위험 표시 | Xi |
| 안전 문구(S) | 24/25-26-37 |
| 위험 참고 사항 | Irritant |
| 위험 등급 | Eye Irrit. 2Skin Sens. 1 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 103-16-2(Hazardous Substances Data) |
용도
개요
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.
용도
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.
제조 및 합성 방법
제조 방법
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%.