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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

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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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