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)

Flash point:

>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

Mequinol(150-76-5)

EPA Substance Registry System

p-Methoxyphenol (150-76-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

24/25-26-37/39-46

OEB

B

OEL

TWA: 5 mg/m3

WGK Germany 

1

RTECS 

SL7700000

Autoignition Temperature

789 °F

TSCA 

Yes

HS Code 

29095090

Hazardous Substances Data

150-76-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 1600 mg/kg

MSDS

• Language:English Provider:4-Methoxyphenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Methoxyphenol Usage And Synthesis

Description

4-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 Properties

4-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.

Uses

4-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.

Synthesis

4-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%.

Definition

ChEBI: P-methoxyphenol is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.

Indications

Mequinol (4-hydroxyanisole) is a substrate of the enzyme tyrosinase and acts as a competitive inhibitor of melanogenesis.

Reactions

4-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 Description

Pink crystals or white waxy solid.

Air & Water Reactions

Sensitive to moisture. Water soluble.

Reactivity Profile

4-Methoxyphenol can react with oxidizing materials.

Hazard

Eye irritant and skin damage.

Health Hazard

4-Methoxyphenol is expected to cause liver and renal toxicity with narcosis, but only at high levels of exposure.

Fire Hazard

Combustible

Flammability and Explosibility

Non flammable

Safety Profile

Poison by intraperitoneal route. A skin irritant. When heated to decomposition it emits acrid smoke and fumes. See also ETHERS.

Potential Exposure

Mutagen, 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 aid

If 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.

storage

Protect 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.

Shipping

UN3335 Aviation regulated solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Purification Methods

Crystallise 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.]

Incompatibilities

Strong oxidizers, strong bases, acid chlorides, acid anhydrides. Under certain conditions, a dust cloud can probably explode if ignited by a spark or flame.

4-Methoxyphenol(150-76-5)Related Product Information

• Dimethyl ether
• 4-Hydroxybenzoic acid
• 4-Hydroxy-D-(-)-2-phenylglycine
• Methylparaben
• p-Anisidine
• Hydroquinone
• 4-Hydroxybenzamide
• Guaiacol
• (Trifluoromethoxy)benzene
• 4-Methoxyphenylacetic acid
• 4-Cyanophenol
• Ethylbenzene
• Anisole
• 4-Hydroxybenzaldehyde
• 3-(4-Hydroxyphenyl)propionic acid
• p-(2-Methoxyethyl) phenol
• 2-Butoxyethanol
• 4-Hydroxyphenethyl alcohol
• Hydroquinone Monomethyl Ether
• Para Methoxy Phenol