3-Methoxybenzoic acid

Base Information

• Chemical Name: 3-Methoxybenzoic acid
• CAS No.: 586-38-9
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 2918.90
• European Community (EC) Number: 209-574-9
• NSC Number: 27014,9264
• UNII: E2I36FH6QZ
• DSSTox Substance ID: DTXSID2060410
• Nikkaji Number: J6.737G
• Wikidata: Q10395568
• Metabolomics Workbench ID: 45645
• ChEMBL ID: CHEMBL22425
• Mol file: 586-38-9.mol

Synonyms:3-anisic acid;3-methoxybenzoic acid;m-anisic acid

Chemical Property of 3-Methoxybenzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000303mmHg at 25°C
• Melting Point: 105-107 °C(lit.)
• Refractive Index: 1.4945 (estimate)
• Boiling Point: 308 °C at 760 mmHg
• PKA: 4.10(at 25℃)
• Flash Point: 123.3 °C
• PSA: 46.53000
• Density: 1.207 g/cm³
• LogP: 1.39340
• Storage Temp.: Store below +30°C.
• Solubility.: 95% ethanol: soluble50mg/mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in 95% ethanol (50 mg/ml), water (2 mg/ml at 25°C) and methanol.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99%, ^*data from raw suppliers

3-Methoxybenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-20/21/22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: COC1=CC=CC(=C1)C(=O)O
• Uses: 3-Methoxybenzoic acid is used in the synthesis and characterization of 3-methoxybenzoates of europium (III) and gadolinium (III)1. 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

Technology Process of 3-Methoxybenzoic acid

There total 171 articles about 3-Methoxybenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3-methoxyphenyl bromide (2398-37-0) + carbon dioxide (124-38-9,18923-20-1) → 3-Methoxybenzoic acid (586-38-9)

Guidance literature:

3-methoxyphenyl bromide; With bromobenzene; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc; In acetonitrile; at 20 ℃; Inert atmosphere;

carbon dioxide; With palladium diacetate; tricyclohexylphosphine; In tetrahydrofuran; acetonitrile; at 0 ℃; for 5h; under 775.743 Torr; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate; acetonitrile;

DOI:10.1021/ja803435w

Reference yield: 87.0%

3-methoxy-benzaldehyde (591-31-1) → 3-methoxybenzyl alcohol (6971-51-3) + 3-Methoxybenzoic acid (586-38-9)

Guidance literature:

With sodium hydroxide; In water; at 15 ℃; for 2.5h;

DOI:10.1039/c5nj02313k

Reference yield: 81.0%

3-methoxy-benzaldehyde (591-31-1) → 3-methoxybenzyl alcohol (6971-51-3) + 3-methoxybenzyl 3-methoxybenzoate (24318-46-5) + 3-Methoxybenzoic acid (586-38-9)

Guidance literature:

With aluminum (III) chloride; triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1007/s00706-021-02785-9

upstream raw materials:

diazomethane

3-acetoxybenzoic acid

methanol

3-aminophthalic acid

Downstream raw materials:

3-[4-(3-methoxy-benzoylamino)-phenyl]-coumarin

3-methoxybenzonitrile

4,3'-dimethoxybenzophenone

methyl 3-methoxybenzoate

Refernces

• 1、 O'Brien, Connor J.,Nicewicz, David A.. "Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides". supporting information. p. 814 - 816. Retrieved 2021/03/01.
• 2、 Harada, Yumi,Hayashi, Kazuhiko,Ichimaru, Yoshimi,Imai, Masanori,Kojima, Yuki,Maeda, Azusa,Nakayama, Kanae,Sugiura, Kirara. "Efficiency of lithium cations in hydrolysis reactions of esters in aqueous tetrahydrofuran". . p. 581 - 594. Retrieved 2021/06/06.