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54050

Sigma-Aldrich

4-Methoxyphenol

purum, ≥98.0% (HPLC)

Synonym(s):

4-Hydroxyanisole, 4-MP, HQMME, Hydroquinone monomethyl ether, MEHQ, p-Guaiacol

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About This Item

Linear Formula:
CH3OC6H4OH
CAS Number:
150-76-5
Molecular Weight:
124.14
Beilstein:
507924
EC Number:
205-769-8
MDL number:
MFCD00002332
UNSPSC Code:
12352100
PubChem Substance ID:
329758018
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

200

vapor pressure

<0.01 mmHg ( 20 °C)

grade

purum

Assay

≥98.0% (HPLC)

autoignition temp.

789 °F

impurities

≤2% hydroquinone dimethyl ether

bp

243 °C (lit.)

mp

54-56 °C
55-57 °C (lit.)

SMILES string

COc1ccc(O)cc1

InChI

1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

InChI key

NWVVVBRKAWDGAB-UHFFFAOYSA-N

Gene Information

human ... TYR(7299)

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General description

4-Methoxyphenol, a 4-alkoxyphenol, can be synthesized from hydroquinone. It undergoes polymerization in the presence of horseradish peroxidase (enzymatic catalyst) and sodium dodecyl sulfate (surfactant) to afford poly(4-methoxyphenol).

Application

4-Methoxyphenol may be used in to synthesize chiral building blocks such as 1,2-diols. It also has various industrial applications, such as an antioxidant, an inhibitor for the polymerization reactions and a stabilizing agent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H319,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

54050-BULK:
54050-100G:4548173956466
54050-VAR:
54050-500G:4548173956473

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0172
BCCK9367
BCCJ3241
BCCG5232
BCCF3545

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Paolo Ruzza et al.
Journal of medicinal chemistry, 52(15), 4973-4976 (2009-07-16)
We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activatable phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2)
Enantioselective ring opening of epoxides with 4-methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1, 2-diol monoethers.
Iida T, et al.
Angewandte Chemie (International Edition in English), 37(16), 2223-2226 (1998)
Synthesis of poly (4-methoxyphenol) by enzyme-catalyzed polymerization and evaluation of its antioxidant activity.
Zheng K, et al.
New. J. Chem., 37(12), 4185-4191 (2013)
Simple synthesis of non-symmetric 1, 4-dialkoxybenzenes via 4-alkoxyphenols.
Radoslaw M, et al.
Organic Communications, 9(1) (2016)
Lisa M Colosi et al.
Environmental science & technology, 41(3), 891-896 (2007-03-03)
Natural organic matter (NOM) of hydroxylated aromatic character can undergo catalyst-mediated self-coupling reactions to form larger molecular aggregates. Indeed, such reactions are central to natural humification processes. Nonhydroxylated persistent aromatic contaminants such as polychlorinated biphenyls (PCBs) are, conversely, inert with
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