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M19201

Sigma-Aldrich

4-Methoxyphenylacetic acid

ReagentPlus®, 99%

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Synonym(s):
Homoanisic acid
Linear Formula:
CH3OC6H4CH2CO2H
CAS Number:
104-01-8
Molecular Weight:
166.17
Beilstein:
1101737
EC Number:
203-166-4
MDL number:
MFCD00004345
PubChem Substance ID:
24896588
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

99%

bp

140 °C/3 mmHg (lit.)

mp

84-86 °C (lit.)

SMILES string

COc1ccc(CC(O)=O)cc1

InChI

1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

InChI key

NRPFNQUDKRYCNX-UHFFFAOYSA-N

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Application

4-Methoxyphenylacetic acid can be used:
  • To prepare methyl 4-methoxyphenylacetate by esterification with dimethyl carbonate using mesoporous sulfated zirconia catalyst.
  • As a ligand to synthesize pharmacologically important dinuclear gallium(III) and phenyltin(IV) carboxylate metal complexes.
  • As a reactant to synthesize hydroxylated (E)-stilbenes by reacting with substituted benzaldehydes via Perkin reaction.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

379.4 °F

Flash Point(C)

193 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction
Sinha AK, et al.
Tetrahedron, 63(45), 11070-11077 (2007)
Esterification of 4-methoxyphenylacetic acid with dimethyl carbonate over mesoporous sulfated zirconia
Devulapelli VG and Weng H-S
Catalysis Communications, 10(13), 1711-1717 (2009)
Santiago Gómez-Ruiz et al.
Journal of inorganic biochemistry, 102(12), 2087-2096 (2008-09-02)
The reaction of 3-methoxyphenylacetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5-dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV) chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence of triethylamine yielded the compounds [SnPh3(3-MPA)] (1), [SnPh3(4-MPA)] (2), [SnPh3(DMFU)] (3), [SnPh3(BZDO)] (4)
Milena R Kaluderović et al.
European journal of medicinal chemistry, 45(2), 519-525 (2009-11-21)
The reaction of 3-methoxyphenylacetic acid, 4-methoxyphenylacetic acid, mesitylthioacetic acid, 2,5-dimethyl-3-furoic acid and 1,4-benzodioxane-6-carboxylic acid with trimethylgallium (1:1) yielded the dimeric complexes [Me(2)Ga(micro-O(2)CCH(2)C(6)H(4)-3-OMe)](2) (1), [Me(2)Ga(micro-O(2)CCH(2)C(6)H(4)-4-OMe)](2) (2), [Me(2)Ga(micro-O(2)CCH(2)SMes)](2) (3) (Mes=2,4,6-Me(3)C(6)H(2)), [Me(2)Ga{micro-O(2)C(Fur)}](2) (4) (Fur=2,5-dimethylfuran) and [Me(2)Ga{micro-O(2)C(Bdo)}](2) (5) (Bdo=1,4-benzodioxane) respectively. The molecular structure of
Ki Hyun Kim et al.
Bioorganic & medicinal chemistry letters, 21(8), 2270-2273 (2011-03-23)
A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana resulted in the isolation and identification of a new sesquilignan, named berbikonol (1), along with fourteen known lignan derivatives (2-15) and a new phenolic compound, named berfussinol (16)
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