Monobenzon
MONOBENZONE · PBP · HYDROQUINONE MONOBENZYL ETHER · Monobenzone powder · 4-BENZYLOXYPHENOL · Benoquin · Monobenzon · Alba
Identifikatoren & physikalische Daten
| CAS No. | 103-16-2 |
|---|---|
| Summenformel | C13H12O2 |
| Durchschnittliche Molmasse | 200,23 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | Monobenzon |
Chemische & physikalische Eigenschaften
| XLogP | 3,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 167 |
| Stoffklassen | Other Classes -> Other Aromatic Compounds |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical diffusion |
| LogP (Verteilungskoeffizient) | 3.2 |
| Geruch | ODORLESS |
| Dichte | 1.261,26 g/cm3 |
| Color/Form | LUSTROUS LEAFLETS FROM WATERWHITE CRYSTALLINE POWDER |
| Löslichkeit | 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/LChloroform (Slightly), DMSO (Slightly), Methanol (Slightly)slightly soluble |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 122.5 °C110 - 118 °C119-120 °C (lit.) |
| Dampfdruck | 0.0000225 [mmHg] |
| Siedepunkt | 297.96°C (rough estimate) |
| Brechungsindex | 1.5906 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 10.29±0.15(Predicted) |
| Aggregatzustand | Powder, Crystals, and/or Chunks |
| Farbe | Off-white to beige to brown |
| Biologische Quelle | 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 (Verteilungskoeffizient) | 2.651 (est) |
| CAS Datenbank | 103-16-2(CAS DataBase Reference) |
| NIST chemische Informationen | Monobenzone(103-16-2) |
| EPA chemische Informationen | Monobenzone (103-16-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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] |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 4-(phenylmethoxy)- |
| Gefahrenübersicht | 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 |
| Entsorgungsverfahren | 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. |
| Unerwünschte Wirkungen | 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/ |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29095090 |
| RTECS-Nr. | SJ7700000 |
| R-Sätze (R) | 36-43 |
| Toxizität | LD50 i.p. in mice: >600 mg/kg (Takahashi) |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 24/25-26-37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 103-16-2(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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%.