103-16-2

Basic information

• Product Name: PBP
• Synonyms: MONOBENZONE;PBP;P-BENZYLOXYPHENOL;P-HYDROXYPHENYL BENZYL ETHER;HYDROQUINONE MONOBENZYL ETHER;Benzyl hydroquinone;BENZYL P-HYDROXYPHENYL ETHER;4-BENZYLOXYPHENOL
• CAS NO: 103-16-2
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23318
• EINECS: 203-083-3
• Product Categories: API intermediates;Bifunctional Compounds (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;treat Vitiligo;whiten agent;cosmetics;B;Bioactive Small Molecules;Building Blocks;C9 to C20+;Cell Biology;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;API;SANODIN
• Mol File: 103-16-2.mol
• Article Data: 68

Chemical Properties

• Melting Point: 119-120 °C(lit.)
• Boiling Point: 297.96°C (rough estimate)
• Flash Point: 213.4 °C
• Appearance: Off-white to beige to brown/Powder, Crystals, and/or Chunks
• Density: 1,26 g/cm3
• Refractive Index: 1.5906 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 10.29±0.15(Predicted)
• Water Solubility: slightly soluble
• Merck: 14,6248
• BRN: 1958305
• CAS DataBase Reference: PBP(CAS DataBase Reference)
• NIST Chemistry Reference: PBP(103-16-2)
• EPA Substance Registry System: PBP(103-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 24/25-26-37
• WGK Germany: 2
• RTECS: SJ7700000
• TSCA: Yes
• Hazardous Substances Data: 103-16-2(Hazardous Substances Data)

Usage

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.

Chemical Properties

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.

Uses

Different sources of media describe the Uses of 103-16-2 differently. You can refer to the following data:
1. PBP is used as antiinflammatory, antisecretory, antiulcer.
2. Hydroquinone monobenzyl ether is an antidegradant added to rubber products; inhibitor in acrylic resins.
3. 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.

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.

Definition

ChEBI: Monobenzone is the monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation. It has a role as a melanin synthesis inhibitor, a dermatologic drug and an allergen. It derives from a hydroquinone.

Brand name

Benoquin (Valeant).

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.]

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

Upstream product

• 100-39-0 benzyl bromide 
• 123-31-9 hydroquinone 
• 621-91-0 1,4-dibenzyloxybenzene 
• 207500-64-9 4-(benzyloxy)phenyl 4-methylbenzenesulfonate 
• 100-44-7 benzyl chloride 
• 73010-55-6 4-(benzyloxy)-4-methoxy-2,5-cyclohexadien-1-one 
• 50666-95-0 1-(allyloxy)-4-(benzyloxy)benzene 
• 6630-18-8 4-methoxyphenyl benzyl ether 
• 37592-20-4 1,4-bis(allyloxy)benzene 
• 946-80-5 (benzyloxy)benzene 
• 6373-46-2 p-benzyloxyaniline 
• 108-95-2 phenol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 53012-35-4 1-(4-benzyloxyphenoxy)propan-2-one 
• 57991-82-9 4-(benzyloxy)phenyl diethyl phosphate 
• 142746-15-4 bis(4-(benzyloxy)phenoxy)methane 
• 142717-44-0 Ethyl 2-(4-benzyloxyphenoxy)ethanoate 
• 101685-85-2 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-benzyloxy-phenoxy)-tetrahydro-pyran-3-yl ester 
• 181808-27-5 1-benzyloxy-4-[2-(2-methoxyethoxy)ethoxy]benzene 
• 142523-49-7 (4-Benzyloxy-phenoxymethyl)-phosphonic acid diethyl ester 
• 431904-89-1 α-(Benzyl)-ω-(benzyloxy)-(oxy-1,4-phenyleneoxy-1,10-decamethyleneoxy-1,4-phenylene) 
• 106-51-4 p-benzoquinone 
• 100-51-6 benzyl alcohol 
• 23877-66-9 1-[2-[4-(phenylmethoxy)phenoxy]ethyl]pyrrolidine 
• 57725-43-6 1-((4-(2-ethoxyethoxy)phenoxy)methyl)benzene 
• 222422-05-1 (R)-2-((4-(benzyloxy)phenoxy)methyl)oxirane 
• 122797-04-0 (S)-{[4-(Phenylmethoxy)phenoxy]methyl}-oxirane 

Related news

Dual-band PBP (cas 103-16-2) detectors based on InAs/GaSb strained layer superlattices08/16/2019

We report on fabrication of 320 × 256 dual-band (mid-/long-wave infrared) type-II InAs/GaSb strained layer superlattice (T2LS) focal plane array (FPA) with pBp architecture. The simplified fabrication procedure has been utilized to reveal the fundamental electro-optical performance of both abso...detailed

Prevalence of Haemophilus influenzae with alteration of PBP (cas 103-16-2) 3 sequence over a 1-year period in a French hospital: focus on a clinical failure after ceftriaxone treatment08/12/2019

Among 547 Haemophilus influenzae isolates recovered in our center, 45 displayed a phenotype of loss of PBP 3 affinity (8.2%). Two isolates with 6 substitutions in PBP 3 showed decreased susceptibility to third-generation cephalosporins. Clinical data revealed clinical failure after ceftriaxone t...detailed

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