2,6-Dimethoxybenzoic acid

Base Information

• Chemical Name: 2,6-Dimethoxybenzoic acid
• CAS No.: 1466-76-8
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29189010
• European Community (EC) Number: 215-985-4
• NSC Number: 28591
• UNII: G6B3P1LO43
• DSSTox Substance ID: DTXSID4046999
• Nikkaji Number: J136.394H
• Wikidata: Q27161685
• Pharos Ligand ID: FMFTWPKLWSS1
• Metabolomics Workbench ID: 43752
• ChEMBL ID: CHEMBL488609
• Mol file: 1466-76-8.mol

Synonyms:2,6-dimethoxybenzoic acid

Chemical Property of 2,6-Dimethoxybenzoic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.000197mmHg at 25°C
• Melting Point: 185-187 °C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 314.5 °C at 760 mmHg
• PKA: pK1:3.44 (25°C)
• Flash Point: 126.5 °C
• PSA: 55.76000
• Density: 1.214 g/cm³
• LogP: 1.40200
• Storage Temp.: Store below +30°C.
• Solubility.: 14.7g/l soluble
• Water Solubility.: 0.35 g/100 mL (25 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethoxybenzoic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: COC1=C(C(=CC=C1)OC)C(=O)O
• Uses: 2,6-Dimethoxybenzoic Acid is used in the synthesis of indoles as well as coumarins related to Novobiocin (N888500), used as potent inhibitors of heat-shock protein 90 in the treatment of breast cancer.

Technology Process of 2,6-Dimethoxybenzoic acid

There total 37 articles about 2,6-Dimethoxybenzoic 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: 93.0%

2,6-dimethoxybenzaldehyde (3392-97-0) → 6-methoxysalicylaldehyde (700-44-7) + 2,6-dimethoxybenzyl alcohol (16700-55-3) + 2-6-dimethoxybenzoic acid (1466-76-8)

Guidance literature:

2,6-dimethoxybenzaldehyde; With aluminum (III) chloride; In dichloromethane; at -15 - 20 ℃; for 5h; Inert atmosphere; Large scale;

With hydrogenchloride; In dichloromethane; water; at 25 ℃; Inert atmosphere; Large scale;

DOI:10.1021/op049889k

Reference yield: 87.0%

ethyl 2,6-dimethoxybenzoate (1464-96-6) → 2-6-dimethoxybenzoic acid (1466-76-8)

Guidance literature:

With water; indium (III) iodide; silica gel; for 1h; Heating;

DOI:10.1080/00397910008087033

Reference yield: 84.0%

2-(2,6-dimethoxyphenyl)acetic acid (15561-50-9) → 2-6-dimethoxybenzoic acid (1466-76-8)

Guidance literature:

With iodine; dimethyl sulfoxide; at 120 ℃; for 28h; Sealed tube; Green chemistry;

DOI:10.1021/acs.joc.7b00242

upstream raw materials:

2,6-dimethoxytoluene

2,6-dimethoxyacetophenone

2,6-dimethoxybenzonitrile

2,6-Dihydroxybenzoic acid

Downstream raw materials:

methyl 2,6-dimethoxybenzoate

ethyl 2,6-dimethoxybenzoate

2,6-Dihydroxybenzoic acid

2,6-dimethoxybenzoyl chloride

Refernces

• 1、 Arciniegas, Amira,Pérez-Castorena, Ana L.,Meléndez-Aguirre, Mariana,ávila, José Guillermo,García-Bores, Ana María,Villase?or, José Luis,Romo de Vivar, Alfonso. "Chemical Composition and Antimicrobial Activity of Ageratina deltoidea". . . Retrieved 2018.
• 2、 Kreuchunas. "-". . p. 368. Retrieved 1956.
• 3、 Patil, Bhausaheb N.,Sathe, Pratima A.,Parade, Babasao S.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.. "Transition metal free one pot synthesis of aryl carboxylic acids via dehomologative oxidation of styrenes". supporting information. p. 4340 - 4343. Retrieved 2018/11/06.
• 4、 Mallia, Carl J.,Walter, Gary C.,Baxendale, Ian R.. "Flow carbonylation of sterically hindered ortho-substituted iodoarenes". supporting information. p. 1503 - 1511. Retrieved 2016/08/02.