Name: 4-Methoxyphenol
SKU: 150-76-5

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Basic Information

Molecular Structure:
CAS No.:	150-76-5
Name:	4-Methoxyphenol
Article Data:	775

Formula:	C₇H₈O₂
Molecular Weight:	124.139
Synonyms:	4-Hydroxyanisole;Hydroquinone monomethyl ether;Mequinol [INN:DCF];Phenol, 4-methoxy-;p-Hydroxyanisole;p-Methoxyphenol;1-Hydroxy-4-methoxybenzene;4-Methoxyphenol;Monomethyl ether hydroquinone;NSC 4960;Novo-Dermoquinona;P-Guaiacol;PMF (antioxidant);Phenol, 4-methoxy-;UNII-6HT8U7K3AM;USAF AN-7;p-Guaiacol;p-Hydroxyanisole;Mequinol;
EINECS:	205-769-8
Density:	1.109 g/cm³
Melting Point:	56 °C
Boiling Point:	243 °C at 760 mmHg
Flash Point:	120.8 °C
Solubility:	water: 40 g/L (25 °C)
Appearance:	white crystals
Hazard Symbols:	Xn
Risk Codes:	22-36-43
Safety:	24/25-26-37/39-46
PSA:	29.46000
LogP:	1.40080

Synthetic route

: 62790-87-8
4-(tert-butyldimethylsilyloxy)anisole

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With SO3H silica gel In n-heptane at 25℃; for 0.166667h;	100%
With iodine In methanol for 13h; Ambient temperature;	99%
With carbonochloridic acid 1-chloro-ethyl ester In methanol at 20℃; for 4h;	99%

: 13391-35-0
allyl (4-methoxyphenyl) ether

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 70℃;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol at 20℃; for 12h;	96%
With magnesium; lithium tert-butoxide In tetrahydrofuran at 20℃; for 12h;	93%

: 100867-08-1
O-(4-Nitrobenzyl)-4-methoxyphenol

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With indium; ammonium chloride; zinc In ethanol; water for 3h; Reagent/catalyst; Reflux; chemoselective reaction;	100%
With indium; ammonium chloride In ethanol for 18h; Debenzylation; Heating;	81%
With indium; ammonium chloride In methanol for 18h; Heating;	81%

: 5720-07-0
4-methoxyphenylboronic acid

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 8h; Reagent/catalyst; Irradiation; Sonication;	100%
With solid poly(N-vinylpyrrolidone)-hydrogen peroxide complex (PVD-H2O2 complex) In dichloromethane at 20℃; regioselective reaction;	99%
With menadione; sodium hydrogencarbonate; sodium L-ascorbate In ethanol; water at 20℃; under 760.051 Torr; for 24h; pH=8.5; Darkness; Green chemistry;	99%

: 1200-06-2
4-methoxyphenyl acetate

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With triethylamine Photolysis;	100%
With potassium carbonate In methanol at 20℃; for 0.5h;	98%
With acetyl chloride In methanol at 20℃; for 2h;	96%

: 15360-00-6
p-tert-butoxyanisole

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With sodium iodide; cerium(III) chloride In acetonitrile at 40℃; for 2h;	100%
With erbium(III) triflate In methanol at 100℃; for 0.75h; Microwave irradiation;	98%

: 404586-95-4
4-(tert-butoxycarbonyloxy)methoxybenzene

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With erbium(III) triflate In ethanol for 25h; Microwave irradiation;	100%
With methanol; carbon tetrabromide; triphenylphosphine for 4h; Reflux;	92%
With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere;

: 20443-88-3
2-(4-methoxyphenoxy)tetrahydro-2H-pyran

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With methanol; Montmorillonite K-10 clay at 20℃; Methanolytic deprotection;	99%
vanadium(III) chloride In methanol at 20℃; for 0.416667h;	95%
With methanol at 20℃; for 0.5h;	95%

: 6630-18-8
4-methoxyphenyl benzyl ether

A: 150-76-5
4-methoxy-phenol

B: 108-88-3
toluene

Conditions

Conditions	Yield
With formic acid In water at 120℃; Green chemistry;	A 97% B 99%
With 9,10-dihydroanthracene at 224.84℃; Kinetics; Product distribution;
With hydrogen In hexane at 260℃; under 5250.53 Torr; for 10h; Autoclave;	A 93.6 %Chromat. B 82.9 %Chromat.
With isopropyl alcohol at 260℃; under 15001.5 Torr; for 4h; Autoclave; Inert atmosphere; Green chemistry;	A 85 %Chromat. B 88 %Chromat.

: 4-methoxyphenyl β-(trimethylsilyl)ethoxymethyl ether

: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With carbon tetrabromide In methanol Irradiation;	99%

Raw Materials

696-64-0

Downstream Products

87-72-9

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 5 mg/m³
ACGIH TLV: TWA 5 mg/m³

Specification

1. Introduction of 4-Methoxyphenol
4-Methoxyphenol is a pink crystals or white waxy solid.

2. Properties of 4-Methoxyphenol
XLogP3: 1.3
H-Bond Donor: 1
H-Bond Acceptor: 2
EINECS: 205-769-8
Melting Point: 56 °C
Water Solubility: 40 g/L (25 °C)
Stability: Stable. Combustible. Incompatible with halogens, oxidizing agents.
Surface Tension: 38.6 dyne/cm
Density: 1.109 g/cm³
Flash Point: 120.8 °C
Enthalpy of Vaporization: 49.94 kJ/mol
Boiling Point: 243 °C at 760 mmHg
Vapour Pressure: 0.0211 mmHg at 25 °C
Product Categories: Liquid Crystal intermediates; Aromatic Ethers; Phenol&Thiophenol&Mercaptan; API intermediates; Biochemistry; Building Blocks for Liquid Crystals; Functional Materials; Phenols (Building Blocks for Liquid Crystals); Reagents for Oligosaccharide Synthesis

3. Toxicity of 4-Methoxyphenol

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)		National Technical Information Service. Vol. AD691-490,
rat	LD50	oral	1600mg/kg (1600mg/kg)		Kodak Company Reports. Vol. 21MAY1971,

4. Safety Information of 4-Methoxyphenol
Poison by intraperitoneal route. A skin irritant. When heated to decomposition it emits acrid smoke and fumes. See also ETHERS.
Hazard Codes: Harmful

Xn
Risk Statements: 22-36-43
R22:Harmful if swallowed.
R36:Irritating to eyes.
R43:May cause sensitization by skin contact.
Safety Statements: 24/25-26-37/39-46
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S46:If swallowed, seek medical advice immediately and show this container or label.
WGK Germany: 1
RTECS: SL7700000
HS Code: 29095090

5. Preparation of 4-Methoxyphenol
P-anisaldehyde (50 mmol) is dissolved in CH₂Cl₂(100mL) and 2-NO₂C₆H₄SeSeC₆H₄NO₂-2(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 CH₂C_l2 (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 solution (100mL), 10% Na₂CO₃ solution (100mL), water (100mL) and dried over Na₂SO₄. 4-methoxyphenol is obtained by alkaline hydrolysis of the residue. Yield: 93%.

6. Use of 4-Methoxyphenol
Mequinol is a drug used in combination with the drug Tretinoin in the treatment of liver spots. And it is used alone as a topical drug for medical depigmentation. Mequinol is also used as an inhibitor and stabilizer in vinyl and acrylic monomers, acrylonitriles, and various polymers especially for finished products. In ethers, chlorinated hydrocarbons and ethyl cellulose it is used as a stabilizer to inhibit peroxide formation.

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Standards and Recommendations

Specification