2-Hydroxy-3-methoxybenzoic acid

Base Information

• Chemical Name: 2-Hydroxy-3-methoxybenzoic acid
• CAS No.: 877-22-5
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29189900
• European Community (EC) Number: 212-888-9
• NSC Number: 408167,134533
• UNII: 3J31Y0E2IM
• DSSTox Substance ID: DTXSID20236566
• Nikkaji Number: J55.236D
• Wikidata: Q27136978
• Metabolomics Workbench ID: 49740
• ChEMBL ID: CHEMBL450441
• Mol file: 877-22-5.mol

Synonyms:2-hydroxy-3-methoxybenzoic acid

Chemical Property of 2-Hydroxy-3-methoxybenzoic acid

Chemical Property:

• Appearance/Colour: beige powder
• Vapor Pressure: 0.000182mmHg at 25°C
• Melting Point: 147-150 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 315.7 °C at 760 mmHg
• PKA: 2.85±0.10(Predicted)
• Flash Point: 131.7 °C
• PSA: 66.76000
• Density: 1.351 g/cm³
• LogP: 1.09900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99.9% ^*data from raw suppliers

o-Vanillic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC(=C1O)C(=O)O
• Uses: o-Vanillic Acid, is a derivative of Vanillic Acid (V097350), used as a flavoring agent. o-Vanillic Acid, is also a building block used for the synthesis of more complex pharmaceutical compounds such as Warfarin (W498500), and Phenprocoumon (P318820). 2-Hydroxy-3-methoxybenzoic acid was used as internal standard during the simultaneous quantification of acetylsalicylic acid and its metabolite salicylic acid in human plasma by high-performance liquid chromatography. It was used in large-scale synthesis of 7-methoxy-3(2H)-benzofuranone.

Technology Process of 2-Hydroxy-3-methoxybenzoic acid

There total 25 articles about 2-Hydroxy-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: 94.0%

2,3-dimethoxybenzoic acid (1521-38-6) → 3-methoxysalicylic acid (877-22-5)

Guidance literature:

With piperazine; In N,N-dimethyl acetamide; at 150 ℃; for 0.2h;

DOI:10.1055/s-2000-6244

Reference yield: 89.0%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 3-methoxysalicylic acid (877-22-5)

Guidance literature:

With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2007.03.151

Reference yield: 89.0%

2-hydroxy-3-methoxybenzyl alcohol (4383-05-5) → 3-methoxysalicylic acid (877-22-5)

Guidance literature:

With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide; In methanol; at 20 ℃; for 48h; In air;

DOI:10.1055/s-0029-1217115

upstream raw materials:

2,3-dimethoxybenzoic acid

2-benzenesulfonyloxy-3-methoxy-benzoic acid

3-methoxy-2-hydroxybenzaldehyde

n-butyllithium

Downstream raw materials:

3-methoxymethylsalicylate

3-carboxy-4-hydroxy-5-methoxybenzaldehyde

2-hydroxy-3-methoxybenzyl alcohol

2,3-Dihydroxybenzoic acid

Refernces

• 1、 Wuensch, Christiane,Gross, Johannes,Steinkellner, Georg,Lyskowski, Andrzej,Gruber, Karl,Glueck, Silvia M.,Faber, Kurt. "Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction". . p. 9673 - 9679. Retrieved 2014/03/21.
• 2、 Makhlynets, Olga V.,Das, Parthapratim,Taktak, Sonia,Flook, Margaret,Mas-Balleste, Ruben,Rybak-Akimova, Elena V.,Que Jr., Lawrence. "Iron-promoted ortho-And/or ipso-hydroxylation of benzoic acids with H 2O2". experimental part. p. 13171 - 13180. Retrieved 2010/07/03.