Benzofuran-2-carboxylic acid

Base Information

• Chemical Name: Benzofuran-2-carboxylic acid
• CAS No.: 496-41-3
• Molecular Formula: C9H6O3
• Molecular Weight: 162.145
• Hs Code.: 29329985
• European Community (EC) Number: 207-818-9
• NSC Number: 6165
• UNII: 7Z6NMG947L
• DSSTox Substance ID: DTXSID2060090
• Nikkaji Number: J6.092E
• Wikidata: Q27269061
• ChEMBL ID: CHEMBL84095
• Mol file: 496-41-3.mol

Synonyms:Benzofuran-2-carboxylic acid;496-41-3;Coumarilic acid;1-Benzofuran-2-carboxylic acid;Benzo[b]furan-2-carboxylic acid;2-BENZOFURANCARBOXYLIC ACID;Coumarone-2-carboxylic acid;2-Carboxybenzofuran;benzofuran-2-carboxylicacid;MFCD00005848;Benzo(b)furan-2-carboxylic acid;NSC 6165;EINECS 207-818-9;BRN 0124204;UNII-7Z6NMG947L;CHEMBL84095;AI3-03711;7Z6NMG947L;NSC6165;NSC-6165;5-18-06-00419 (Beilstein Handbook Reference);4oyp;BZ2;Maybridge1_002455;2-benzofuranecarboxylic acid;Cambridge id 5102130;benzofuran 2-carboxylic acid;2-Benzofuran carboxylic acid;COUMARILIC ACID [MI];DivK1c_001207;SCHEMBL155789;1-benzofurane-2-carboxylic acid;DTXSID2060090;HMS548H13;1-Benzofuran-2-carboxylic acid #;2,3-benzofuran-2-carboxylic acid;Benzofuran-2-carboxylic acid, 99%;BBL018112;BDBM50345230;STK293001;AKOS000103488;AB00533;CS-W004676;SDCCGMLS-0065938.P001;SS-6002;CDS1_000167;NCGC00324555-01;LS-34970;SY005603;A7391;AM20050579;B1981;BB 0244005;FT-0622682;EN300-16967;O11693;AB01319519-02;AN-278/25047013;J-640024;J-800026;Q-101915;Q27269061;Z56839706;F3096-1740

Chemical Property of Benzofuran-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193-196 °C(lit.)
• Refractive Index: 1.649
• Boiling Point: 313.379 °C at 760 mmHg
• PKA: 3.12±0.30(Predicted)
• Flash Point: 143.327 °C
• PSA: 50.44000
• Density: 1.364 g/cm³
• LogP: 2.13100
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol,Ethanol,Acetone
• Water Solubility.: partially soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.031694049
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Benzofuran-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(O2)C(=O)O
• Uses: Benzofuran-2-carboxylic acid was used in the synthesis of the oxymethyl-modified coumarinic acid-based cyclic DADLE (H-Tyr-D-Ala-Gly-Phe-D-Leu-OH) prodrug.

Technology Process of Benzofuran-2-carboxylic acid

There total 54 articles about Benzofuran-2-carboxylic 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: 95.0%

1-benzofurane (271-89-6) + carbon dioxide (124-38-9,18923-20-1) → Benzofuran-2-carboxylic acid (496-41-3)

Guidance literature:

1-benzofurane; With (PMDETA)₂K₂Mg(CH₂SiMe₃)₄; for 1.5h; Inert atmosphere; Schlenk technique;

carbon dioxide; for 1h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1039/c4cc05305b

Reference yield: 90.0%

benzofuran-2-ylglyoxal (40749-31-3) → Benzofuran-2-carboxylic acid (496-41-3)

Guidance literature:

With iodine; dimethyl sulfoxide; at 180 ℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;

DOI:10.1039/c5ob01015b

Reference yield: 87.0%

2-bromo-1-benzofuran (54008-77-4) + formyl acetic anhydride (2258-42-6) → Benzofuran-2-carboxylic acid (496-41-3)

Guidance literature:

2-bromo-1-benzofuran; formyl acetic anhydride; With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In water; pH=Ca. 4 - 6;

DOI:10.1080/00397911.2010.528851

upstream raw materials:

2-bromo-1-benzofuran

3-bromobenzofuran

n-butyllithium

diethyl ether

Downstream raw materials:

methyl benzofuran-2-carboxylate

ethyl coumarilate

3-phenyl-2,3-dihydro-benzofuran-2-carboxylic acid

1-benzofurane

Refernces

• 1、 Rocke, Benjamin N.,Conn, Edward L.,Eisenbeis, Shane A.,Ruggeri, Roger B.. "1,4-Addition of an aryllithium reagent to diethyl ketomalonate. Scalable synthesis of ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate". . p. 5467 - 5470. Retrieved 2012.
• 2、 Bhaskar, K.,Yadav, J. S.. "Synthesis and biological evaluation of a series of novel benzofuran-2-carboxylate 1,2,3-triazoles". . p. 767 - 774. Retrieved 2021/09/28.
• 3、 Bergonzini, Giulia,Brandt, Peter,Fricke, Florian,Johansson, Magnus J.,K?nig, Burkhard,Schmalzbauer, Matthias,Svejstrup, Thomas D.. "Redox-Neutral Photocatalytic C?H Carboxylation of Arenes and Styrenes with CO2". supporting information. p. 2658 - 2672. Retrieved 2020/10/07.