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Hydroquinone Monomethyl Ether is a colorless to white, waxy solid with an odor of caramel and phenol.
A combustible solid.
Molecular weight= 124.15;Boiling point=243℃; Freezing/Melting point=5253℃; Flash point=132℃.
Hydroquinone Monomethyl Ether is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.
CAS: 150-76-5
MF: C7H8O2
MW: 124.14
EINECS: 205-769-8
Synonyms
Eastman HQMME;ethermonomethyliqued’hydroquinone;Hqmme;Hydroquinone methyl ether;hydroquinonemethylether;Leucobasal;Leucodine b;leucodineb
Hydroquinone Monomethyl Ether is a substrate of the enzyme tyrosinase and acts as a competitive inhibitor of melanogenesis.
Hydroquinone monomethyl ether, MeHQ or 4-methoxyphenol, is an organic compound with the formula CH3OC6H4OH.
Hydroquinone Monomethyl Ether is a phenol with a methoxy group in the para position.
Hydroquinone Monomethyl Ether is a colorless solid.
Hydroquinone Monomethyl Ether is used in dermatology and organic chemistry.
Hydroquinone Monomethyl Ether is a solid used in leather and textile manufacturing.
Hydroquinone Monomethyl Ether functions as an intermediate and stabilizer, offering UV resistance to enhance the durability and longevity of materials.
Hydroquinone Monomethyl Ether is essential for stabilizing formulations and improving the performance of textiles and leather products.
Hydroquinone Monomethyl Ether, MeHQ or 4-methoxyphenol, is an organic compound with the formula CH3OC6H4OH.
Hydroquinone Monomethyl Ether is a phenol with a methoxy group in the para position.
A colorless solid, Styrene Monomer is used in dermatology and organic chemistry.
Hydroquinone Monomethyl Ether Chemical Properties
Melting point: 56 °C
Boiling point: 243 °C(lit.)
Density: 1,55 g/cm3
Vapor density: 4.3 (vs air)
Vapor pressure: <0.01 mm Hg ( 20 °C)
Refractive index: 1.5286 (estimate)
Fp: >230 °F
Storage temp.: Store below +30°C.
Solubility: Soluble in acetone, ethyl acetate, ethanol, ether, benzene and carbon tetrachloride.
Form: Liquid
pka: 10.21(at 25℃)
Color: Clear colorless to pale yellow
Odor: at 1.00?%?in?dipropylene glycol. phenolic
PH: 5.1 (30g/l, H2O, 20℃)
Odor Threshold: 0.0027ppm
Water Solubility: 40 g/L (25 ºC)
BRN: 507924
Exposure limits ACGIH: TWA 5 mg/m3
NIOSH: TWA 5 mg/m3
Stability: Stable. Combustible. Incompatible with halogens, oxidizing agents.
InChIKey: NWVVVBRKAWDGAB-UHFFFAOYSA-N
LogP: 1.3 at 20℃
CAS DataBase Reference: 150-76-5(CAS DataBase Reference)
NIST Chemistry Reference: Styrene Monomer (150-76-5)
EPA Substance Registry System: Hydroquinone Monomethyl Ether (150-76-5)
Chemical Properties
Hydroquinone Monomethyl Ether is a colorless to white, waxy solid with an odor of caramel and phenol.
Hydroquinone Monomethyl Ether is a combustible solid.
Hydroquinone Monomethyl Ether is used as an inhibitor for acrylic monomers and as a stabilizer for chlorinated hydrocarbons, ethyl cellulose, and UV inhibitors.
Uses
Hydroquinone Monomethyl Ether is an active ingredient and used in dermatology.
Hydroquinone Monomethyl Ether is employed as a pharmaceutical drug in skin depigmentation.
Hydroquinone Monomethyl Ether is used as polymerization inhibitors.
For example, in the radical polymerization of acryaltes and styrene monomers.
Hydroquinone Monomethyl Ether is also used as an intermediate in the preparationagrochemicals, liquid crystals.
Hydroquinone Monomethyl Ether acts as a stabilizer for the formulation of inks, toners and adhesives.
Hydroquinone Monomethyl Ether is mainly used as an additive for textile and leather industries.
Hydroquinone Monomethyl Ether is a common active ingredient in topical drugs used for skin depigmentation.
As a topical drug Hydroquinone Monomethyl Ether is often mixed with tretinoin, a topical retinoid.
A common formulation for this drug is an ethanolic solution of 2% mequinol and 0.01% tretinoin by mass.
Dermatologists commonly prescribe the drug to treat liver spots.
Lower dosages of Hydroquinone Monomethyl Ether have been used in conjunction with a Q-switched laser to depigment skin in patients with disseminated idiopathic vitiligo.
Synthesis
Hydroquinone Monomethyl Ether was synthesised according to Oxidation with H2O2 and a Diselenide catalyst.
p-Anisaldehyde (50 mmol) is dissolved in CH2Cl2 (100mL) and (o-NO2PhSe)2 (2 mmol) and 30% H2O2 (13mL, 128 mmol) are added.
The mixture is stirred magnetically at room temperature (water bath) for 30 minutes.
Insoluble catalyst is removed by filtration and washed with CH2Cl2 (20mL) and water (20mL).
Hydroquinone Monomethyl Ether can be reused after drying.
To the filtrate and washings, water (100mL) is added, and the layers are separated after shaking.
The organic layer is washed subsequently with 10% NaHSO3 (100mL), 10% Na2CO3 (100mL), water (100mL) and dried over Na2SO4.
Hydroquinone Monomethyl Ether is obtained by alkaline hydrolysis of the residue. Yield: 93%.
Reactions
Hydroquinone Monomethyl Ether may be used in the synthesis of butylated hydroxy anisoles via alkylation with methyl tert-butyl ether over a non-zeolitic solid acidic catalyst.
This process is eco-friendly when compared to the Friedel-Crafts alkylation reaction.
Hydroquinone Monomethyl Ether may also react with aqueous nitrous acid to form 2-nitro-4-methoxyphenol and benzoquinone in varying ratios depending on the reaction conditions.
Hydroquinone Monomethyl Ether can be used as a building block in designing β-cyclodextrin 4-methoxyphenol conjugates that can be potential ligands for drug complexation.
Production Method
Hydroquinone Monomethyl Ether can be prepared by using hydroquinone as raw material, dimethyl sulfate as methylating agent, or methanol as methylating agent under high temperature, high pressure and catalysis.
Another newer method is the reaction of Hydroquinone Monomethyl Ether with methanol in the presence of p-benzoquinone.
Methanol and concentrated sulfuric acid are mixed evenly, hydroquinone is added, heated and refluxed, and the methanol solution of p-benzoquinone is added dropwise for 3 hours.
Cool, neutralize with 40% sodium hydroxide solution, and filter out sodium sulfate precipitate.
After methanol is recovered from the filtrate, Hydroquinone Monomethyl Ether is extracted with ether, the extract is evaporated to remove ether, then Hydroquinone Monomethyl Ether is distilled under reduced pressure, and the 110-112 ℃(0.53kPa) fraction is collected to obtain the finished product.
The yield was 76%.
