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4-Methoxyphenol

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CAS:150-76-5
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4-Methoxyphenol Basic information
Product Name:4-Methoxyphenol
Synonyms:ethermonomethyliqued’hydroquinone;hydroquinonemethylether;Leucodine b;leucodineb;Mechinolum;Mequinol (INN);monomethyletherhydroquinone;monomethyletherofhydroquinone
CAS:150-76-5
MF:C7H8O2
MW:124.14
EINECS:205-769-8
Product Categories:Liquid Crystal intermediates;Phenol&Thiophenol&Mercaptan;API intermediates;Biochemistry;Building Blocks for Liquid Crystals;Functional Materials;Phenols (Building Blocks for Liquid Crystals);Reagents for Oligosaccharide Synthesis;Aromatic Ethers;organic synthesis;Aromatics;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;150-76-5
Mol File:150-76-5.mol
4-Methoxyphenol Structure
4-Methoxyphenol 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
pka10.21(at 25℃)
color Clear colorless to pale yellow
PH5.1 (30g/l, H2O, 20℃)
Odorat 1.00?%?in?dipropylene glycol. phenolic
Odor Threshold0.0027ppm
Water Solubility 40 g/L (25 ºC)
BRN 507924
Exposure limitsACGIH: TWA 5 mg/m3
NIOSH: TWA 5 mg/m3
Stability:Stable. Combustible. Incompatible with halogens, oxidizing agents.
InChIKeyNWVVVBRKAWDGAB-UHFFFAOYSA-N
LogP1.3 at 20℃
CAS DataBase Reference150-76-5(CAS DataBase Reference)
NIST Chemistry ReferenceMequinol(150-76-5)
EPA Substance Registry Systemp-Methoxyphenol (150-76-5)
Safety Information
Hazard Codes Xn
Risk Statements 22-36-43
Safety Statements 24/25-26-37/39-46
WGK Germany 1
RTECS SL7700000
Autoignition Temperature789 °F
TSCA Yes
HS Code 29095090
Hazardous Substances Data150-76-5(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1600 mg/kg
MSDS Information
ProviderLanguage
4-Methoxyphenol English
SigmaAldrich English
ACROS English
ALFA English
4-Methoxyphenol Usage And Synthesis
Description4-Methoxyphenol 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℃. Hazard Identification (based on NFPA-704 M Rating System): Health 2, Flammability 1, Reactivity 0. Slightly soluble in water.
Chemical Properties4-Methoxyphenol is a colorless to white, waxy solid with an odor of caramel and phenol. It is a combustible solid. It is used as an inhibitor for acrylic monomers and as a stabilizer for chlorinated hydrocarbons, ethyl cellulose, and UV inhibitors.
Uses4-Methoxyphenol is an active ingredient and used in dermatology. It is employed as a pharmaceutical drug in skin depigmentation. It is used as polymerization inhibitors. For example, in the radical polymerization of acryaltes and styrene monomers. It is also used as an intermediate in the preparationagrochemicals, liquid crystals. It acts as a stabilizer for the formulation of inks, toners and adhesives. It is mainly used as an additive for textile and leather industries.
IndicationsMequinol (4-hydroxyanisole) is a substrate of the enzyme tyrosinase and acts as a competitive inhibitor of melanogenesis.
Synthesis4-Methoxyphenol 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). It 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. 4-methoxyphenol is obtained by alkaline hydrolysis of the residue. Yield: 93%.
DefinitionChEBI: P-methoxyphenol is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.
Reactions4-methoxyphenol(4-MP) 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. 4-MP may also react with aqueous nitrous acid to form 2-nitro-4-methoxyphenol and benzoquinone in varying ratios depending on the reaction conditions. 4-MP can be used as a building block in designing β-cyclodextrin 4-methoxyphenol conjugates that can be potential ligands for drug complexation.
Synthesis Reference(s)The Journal of Organic Chemistry, 42, p. 1479, 1977 DOI: 10.1021/jo00428a054
Synthesis, p. 751, 1983 DOI: 10.1055/s-1983-30501
Tetrahedron Letters, 34, p. 7667, 1993 DOI: 10.1016/S0040-4039(00)61534-4
General DescriptionPink crystals or white waxy solid.
Air & Water ReactionsSensitive to moisture. Water soluble.
Reactivity Profile4-Methoxyphenol can react with oxidizing materials.
HazardEye irritant and skin damage.
Health Hazard4-Methoxyphenol is expected to cause liver and renal toxicity with narcosis, but only at high levels of exposure.
Fire HazardCombustible
Flammability and ExplosibilityNon flammable
Safety ProfilePoison by intraperitoneal route. A skin irritant. When heated to decomposition it emits acrid smoke and fumes. See also ETHERS.
Potential ExposureMutagen, Primary Irritant. This compound is used in the manufacture of antioxidants, pharmaceuticals, plasticizers, and dyestuffs. It is used as a stabilizer and UV inhibitor in various polymers.
First aidIf this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
storageProtect containers from physical damage. Store in tightly closed containers in a cool, well-ventilated area. Sources of ignition, such as smoking and open flames, are prohibited where 4-methoxyphenol is used, handled, or stored in a manner that could create a potential fire or explosion hazard.
ShippingUN3335 Aviation regulated solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification MethodsCrystallise 4-methoxyphenol from *benzene, pet ether or H2O, and dry it under vacuum over P2O5 at room temperature. Sublime it in vacuo. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 6 IV 5717.]
IncompatibilitiesStrong oxidizers, strong bases, acid chlorides, acid anhydrides. Under certain conditions, a dust cloud can probably explode if ignited by a spark or flame.
Tag:4-Methoxyphenol(150-76-5) Related Product Information
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