Monobenzone

Base Information

• Chemical Name: Monobenzone
• CAS No.: 103-16-2
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Hs Code.: 29095090
• European Community (EC) Number: 203-083-3
• NSC Number: 758211,33918,2132
• UNII: 9L2KA76MG5
• DSSTox Substance ID: DTXSID2020717
• Nikkaji Number: J5.012A
• Wikipedia: Monobenzone
• Wikidata: Q2768526
• NCI Thesaurus Code: C992
• Pharos Ligand ID: LSZJYUAA34AZ
• Metabolomics Workbench ID: 42930
• ChEMBL ID: CHEMBL1388
• Mol file: 103-16-2.mol

Synonyms:agerite alba;Benoquin;hydroquinone monobenzyl ether;monobenzone;monobenzyl ether hydroquinone;Novo-depigman;p-(benzyloxy)phenol

Chemical Property of Monobenzone

Chemical Property:

• Appearance/Colour: cream to beige-light brownish crystals
• Melting Point: 119-120 °C(lit.)
• Refractive Index: 1.5906 (estimate)
• Boiling Point: 359.1 °C at 760 mmHg
• PKA: 10.29±0.15(Predicted)
• Flash Point: 213.4 °C
• PSA: 29.46000
• Density: 1.16 g/cm³
• LogP: 2.97120
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 167

Purity/Quality:

98%, ^*data from raw suppliers

Phosphatidylethanolamine Binding Protein 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 24/25-26-37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)COC2=CC=C(C=C2)O
• Recent EU Clinical Trials: Local immunotherapy by the synergism of monobenzone and imiquimod cream (MI) for cutanous metastases in stage III-IV melanoma patients.
• Description: 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.
• Uses: PBP is used as antiinflammatory, antisecretory, antiulcer. Hydroquinone monobenzyl ether is an antidegradant added to rubber products; inhibitor in acrylic resins. 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.
• Indications: Monobenzone (Benoquin) potently inhibits melanin production and destroys melanocytes. Like hydroquinone, monobenzone was originally introduced for the topical treatment of disorders of excess melanin pigmentation, including melasma. It is now used only to permanently depigment the remaining normally pigmented skin in patients with extensive vitiligo. Irritant and allergic contact dermatitis are common side effects.

Technology Process of Monobenzone

There total 55 articles about Monobenzone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

potassium (4-(benzyloxy)phenyl)trifluoroborate → 4-Benzyloxyphenol (103-16-2)

Guidance literature:

With Oxone; water; In acetone; at 20 ℃; for 0.0333333h;

DOI:10.1021/jo102208d

Reference yield: 95.7%

[4-(benzyloxy)phenyl]boronic acid (146631-00-7) → 4-Benzyloxyphenol (103-16-2)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; water; at 20 ℃; for 4h; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.tet.2021.132411

Reference yield: 95.0%

4-(benzyloxy)phenyl 4-methylbenzenesulfonate (207500-64-9) → 4-Benzyloxyphenol (103-16-2)

Guidance literature:

With magnesium; In methanol; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00314-1

upstream raw materials:

benzyl bromide

hydroquinone

benzyl chloride

4-methoxyphenyl benzyl ether

Downstream raw materials:

(2RS,4'R,8'R)-Tocol

1-benzyloxy-4-(2,4-dinitro-phenoxy)-benzene

2-(4-benzyloxyphenoxy)ethyl bromide

diethyl-[2-(4-benzyloxy-phenoxy)-ethyl]-amine

Refernces

• 1、 Yamada, Makoto,Watanabe, Shin-Ichi,Hoshino, Osamu,Ishizaki, Miyuki,Hayashida, Maiko,Tanaka, Atsuko,Hara, Hiroshi. "A facile method for deprotection of O-allylphenols". . p. 1220 - 1221. Retrieved 2003.
• 2、 Yang, Guichun,Chen, Zuxing,Zhang, Zhaojun,Qiu, Xiaoling. "Novel synthesis of monoethers of hydroquinone and resorcinol on soluble polymer-supports". . p. 3637 - 3642. Retrieved 2002.
• 3、 Guzman,Mendoza,Garcia,Garibay,Oliveras,Maldonado. "Baeyer-Villiger oxidation of β-aryl substituted unsaturated carbonyl compounds with hydrogen peroxide and catalytic selenium dioxide". . p. 2121 - 2133. Retrieved 1995.
• 4、 Yasuhara, Akito,Kasano, Atsushi,Sakamoto, Takao. "An efficient method for the deallylation of allyl aryl ethers using electrochemically generated nickel". . p. 4211 - 4213. Retrieved 1999.
• 5、 Rowe et al.. "-". . p. 1622. Retrieved 1958.
• 6、 Santos, Wagner C. C.,Dias, Kevin A.,Santos, Leidaiany P.,Kisukuri, Camila M.,Rodrigues, Thenner S.,Geonmonond, Rafael S.,Camargo, Pedro H. C.,Andrade, Leandro H.. "Evaluating Gold and Selenium Chemistry for Selective Transformations of Lignin Model Compounds". . p. 1376 - 1383. Retrieved 2018.
• 7、 Peng, Yungui,Ji, Changyun,Chen, Yingchun,Huang, Chengzhi,Jiang, Yaozhong. "An efficient and selective deprotecting method for methoxymethyl ethers". . p. 4325 - 4330. Retrieved 2004.
• 8、 -. "Aryl phenol compound as well as synthesis method and application thereof". Paragraph 0162-0165. . Retrieved 2021/05/12.
• 9、 Zhu, Runqing,Sun, Qianqian,Li, Jing,Li, Luohao,Gao, Qinghe,Wang, Yakun,Fang, Lizhen. "Para -Selective hydroxylation of alkyl aryl ethers". supporting information. p. 13190 - 13193. Retrieved 2021/12/16.