Merck
All Photos(3)

117714

Sigma-Aldrich

3-Methoxybenzoic acid

ReagentPlus®, 99%

Synonym(s):
m-Methylsalicylic acid, m-Anisic acid
Linear Formula:
CH3OC6H4CO2H
CAS Number:
Molecular Weight:
152.15
Beilstein:
508838
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

99%

bp

170-172 °C/10 mmHg (lit.)

mp

105-107 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear, colorless to faintly yellow

SMILES string

COc1cccc(c1)C(O)=O

InChI

1S/C8H8O3/c1-11-7-4-2-3-6(5-7)8(9)10/h2-5H,1H3,(H,9,10)

InChI key

XHQZJYCNDZAGLW-UHFFFAOYSA-N

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General description

3-Methoxybenzoic acid is an important intermediate in the synthesis of natural products.

Application

3-Methoxybenzoic acid was used in the synthesis and characterization of 3-methoxybenzoates of europium (III) and gadolinium (III). It was used in conversion of aromatic carboxylic acids into methyl esters and reduction to the corresponding primary alcohols using a sodium borohydride-THF-methanol system.

Packaging

25, 100 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Sodium borohydride reduction of aromatic carboxylic acids via methyl esters.
Saeed A and Ashraf Z.
Journal of Chemical Sciences (Bangalore), 118(5), 419-423 (2006)
Synthesis, characterization and thermal behaviour of solid-state compounds of europium (III) and gadolinium (III) 3-methoxybenzoate.
Dametto PR, et al.
Journal of Thermal Analysis and Calorimetry, 97(2), 765-768 (2009)
Thi-Huu Nguyen et al.
Organic letters, 7(12), 2445-2448 (2005-06-04)
[reaction: see text] If employed in THF at 0 degrees C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand.
K A DeWeerd et al.
Applied and environmental microbiology, 54(5), 1237-1242 (1988-05-01)
O-methyl substituents of aromatic compounds can provide C1 growth substrates for facultative and strict anaerobic bacteria isolated from diverse environments. The mechanism of the bioconversion of methoxylated benzoic acids to the hydroxylated derivatives was investigated with a model substrate and
N Dodoff et al.
Journal of inorganic biochemistry, 54(3), 221-233 (1994-05-15)
The complexes [Pt(bah)2X2], [Pt(NH3)(bah)Cl2].0.5H2O, [Pt(mbah)2X2], and [Pt(NH3)(mbah)Cl2] (bah = benzoic acid hydrazide, mbah = 3-methoxybenzoic acid hydrazide; X = Cl, Br, I) have been prepared and characterized by elemental analysis, electric conductivity, IR, 1H NMR, and electronic spectra. A cis-square

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