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103-16-2

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103-16-2 Usage

Description

Monobenzone, also known as 4-(Benzyloxy)phenol or hydroquinone monobenzyl ether (MBEH), is an organic chemical in the phenol family with the chemical formula C6H5CH2OC6H4OH. It is used as a topical drug for medical depigmentation and is a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. Monobenzone is a melanin synthesis inhibitor, a dermatologic drug, and an allergen, and it derives from hydroquinone.

Uses

Used in Pharmaceutical Industry:
Monobenzone is used as a topical drug for medical depigmentation. It is applied topically to the skin to increase the excretion of melanin from melanocytes, resulting in a depigmenting effect. This action is thought to be responsible for the drug's effectiveness in treating conditions such as melasma and other hyperpigmentation disorders.
Used in Chemical Industry:
Monobenzone is used as an antidegradant added to rubber products, helping to prevent the degradation of rubber and improving its durability. It also serves as an inhibitor in acrylic resins, contributing to the stability and performance of these materials.
Used in Synthesis:
Monobenzone is used in the synthesis of bis(4-benzyloxyphenoxy)phenyl phosphine oxide, which is an important intermediate in the production of various chemical compounds.
Used in Dye Industry:
Monobenzone plays an essential role in the preparation of hetaryl-azophenol dyes via heterocyclic amines in nitrosyl sulfuric acid. It is also used for polyester fiber dyeing, providing a means to achieve specific colorations and properties in the fibers.
Used in Rubber Industry:
In the rubber industry, Monobenzone acts as a depigmenting agent, which can be useful for altering the color or appearance of rubber products.
Brand Name:
Monobenzone is marketed under the brand name Benoquin by Valeant Pharmaceuticals.

Preparation

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%.

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.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 5129, 1992 DOI: 10.1016/S0040-4039(00)61209-1

Purification Methods

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 103-16-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 103-16:
(5*1)+(4*0)+(3*3)+(2*1)+(1*6)=22
22 % 10 = 2
So 103-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H14O.C6H6O2/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14;7-5-1-2-6(8)4-3-5/h1-10H,11-12H2;1-4,7-8H

103-16-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (A14843)  4-Benzyloxyphenol, 98+%   

  • 103-16-2

  • 25g

  • 366.0CNY

  • Detail
  • Alfa Aesar

  • (A14843)  4-Benzyloxyphenol, 98+%   

  • 103-16-2

  • 50g

  • 623.0CNY

  • Detail
  • Alfa Aesar

  • (A14843)  4-Benzyloxyphenol, 98+%   

  • 103-16-2

  • 100g

  • 1018.0CNY

  • Detail
  • Alfa Aesar

  • (A14843)  4-Benzyloxyphenol, 98+%   

  • 103-16-2

  • 250g

  • 2163.0CNY

  • Detail
  • Alfa Aesar

  • (A14843)  4-Benzyloxyphenol, 98+%   

  • 103-16-2

  • 1000g

  • 7119.0CNY

  • Detail
  • USP

  • (1445506)  Monobenzone  United States Pharmacopeia (USP) Reference Standard

  • 103-16-2

  • 1445506-200MG

  • 4,588.74CNY

  • Detail

103-16-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name monobenzone

1.2 Other means of identification

Product number -
Other names 4-Benzyloxyphenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-16-2 SDS

103-16-2Related news

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103-16-2Relevant articles and documents

Expedient and simple method for regeneration of alcohols from toluenesulfonates using Mg-MeOH

Sridhar, Madabhushi,Kumar, B. Ashok,Narender

, p. 2847 - 2850 (1998)

Efficient conversion of toluenesulfonates to corresponding alcohols with Mg-MeOH is described.

Photoconductive bent-core liquid crystalline radicals with a paramagnetic polar switchable phase

Shivakumar, Kilingaru I.,Pociecha, Damian,Szczytko, Jacek,Kapu?ciński, Szymon,Monobe, Hirosato,Kaszyński, Piotr

, p. 1083 - 1088 (2020)

A series of self-organizing bent-core derivatives 1[12,n], containing a highly π-delocalized stable radical as the central angular structural element, is described. The planarity of the open-shell core permits efficient π-π stacking, which results in the formation of B2 and soft crystalline phases above 100 °C. Optical, XRD and dielectric analyses of 1[12,12] indicate that the ground state of the observed B2 phase is polar antiferroelectric of type SmCAPA exhibiting tristable electro-optical switching. SQUID and EPR measurements revealed strong antiferromagnetic spin-spin exchange interactions below the isotropic phase, which have been estimated at θ = -46 cm-1 with the Curie-Weiss law. Transient photoconductivity was observed in the B2 phase with a hole carrier mobility μh of 1.4 × 10-4 cm2 V-1 s-1

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo

, (2021)

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Synthesis and liquid crystal property of new fluoro coumarin carboxylates

Mahadevan, Kittappa M.,Harishkumar, Hosanagara N.,Masagalli, Jagadeesh N.,Srinivasa, Hosapalya T.

, p. 20 - 35 (2013)

New liquid crystalline 4-alkoxyphenyl-coumarin-3-carboxylates 6a-e, 7a-g, 8a-e, and 9a-e were prepared by reacting various coumarin-3-carboxylic acids 5a-d with 4-(alkoxy) phenols 4a-g in the presence of 1(3-dimethylaminopropyl-3- ethylcarbodiimide/dimethyl amino pyridine (EDCI/DMAP) as a coupling agent. The structures of the new coumarin derivatives were confirmed by spectral analysis and the liquid crystalline property was established by polarizing optical microscope and by differential scanning calorimetric techniques. The diethyl amine and morpholine were taken as electron-donating and -CF3 as electron-withdrawing groups at the seventh position of the coumarin-3-carboxylic acids to check the mesomorphic property in all new 4-alkoxyphenyl-coumarin-3- carboxylates. Among them, only 4-alkoxyphenyl-7-triflouromethyl-coumarin-3- carboxylates 7a-g exhibited liquid crystalline SmA phase.

Development of a catalytic electron transfer system mediated by transition metal ate complexes: Applicability and tunability of electron-releasing potential for organic transformations

Uchiyama, Masanobu,Matsumoto, Yotaro,Nakamura, Shinji,Ohwada, Tomohiko,Kobayashi, Nagao,Yamashita, Natsuno,Matsumiya, Atsushi,Sakamoto, Takao

, p. 8755 - 8759 (2004)

We have developed a catalytic electron transfer (ET) system composed of a transition metal ate complex (Me3M(II)Li; M = Co(II), Mn(II), Fe(II)) and magnesium. This system (catalytic Me3M(II)Li/Mg) turned out to be effective for various ET reactions, such as the desulfonylation of N-phenylsulfonyl amides, and others (the chemoselective cleavage of O-allyl groups, the reduction of nitro groups, the partial reduction of diketones, and the reductive coupling of diphenyliodonium salt). The ET ability of this system can be tuned by changing the ligands of the ate complexes. This tunability was experimentally and electrochemically demonstrated: alkoxy-ligated and dianion-type ET ate complexes showed attenuated and enhanced reducing abilities, respectively. The modification of the ET abilities was evaluated by means of electrochemical measurements and chemical reactions. These results provide a basis for the design of various tailor-made ET ate complexes.

An efficient and selective deprotection of allyl ethers by a CeCl3.7H2O- NaI system

Thomas, R. Mathew,Reddy, G. Sudhakar,Iyengar

, p. 7293 - 7294 (1999)

A mild, novel and chemoselective method for the deprotection of allyl ethers by a CeCl3.7H2O- NaI system is described.

LOW-VALENT TITANIUM: A NEW APPROACH TO DEPROTECTION OF ALLYL AND BENZYL GROUPS

Kadam, S. M.,Nayak, S. K.,Banerji, A.

, p. 5129 - 5132 (1992)

A novel method for the deprotection of allyl and benzyl derivatives of alcohols and phenols by low-valent titanium is reported.The possible mechanism is discussed.

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang

, p. 7633 - 7640 (2021/09/22)

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

Synthetic method 4 - alkoxyphenol compounds

-

Paragraph 0038-0040, (2021/09/29)

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

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