1914-60-9

Basic information

• Product Name: 2,3-Dihydro-1-benzofuran-2-carboxylic acid
• Synonyms: 2,3-DIHYDRO-1-BENZOFURAN-2-CARBOXYLIC ACID;2,3-DIHYDRO-BENZOFURAN-2-CARBOXYLIC ACID;AKOS BBS-00006837;2,3-Dihydro-1-Benzofurane-2-CarboxylicAcid;2,3-Dihydrobenzo[b]furan-2-carboxylic acid;2-Benzofurancarboxylic acid, 2,3-dihydro-;2,3-Dihydro-1-benzofuran-2-carboxylic acid, 2-Carboxy-2,3-dihydrobenzo[b]furan
• CAS NO: 1914-60-9
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.16
• Product Categories: Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids;Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids
• Mol File: 1914-60-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 116-118
• Boiling Point: 340.539 °C at 760 mmHg
• Flash Point: 144.317 °C
• Appearance: /
• Density: 1.347 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: 2-8°C
• PKA: 3.17±0.20(Predicted)
• CAS DataBase Reference: 2,3-Dihydro-1-benzofuran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydro-1-benzofuran-2-carboxylic acid(1914-60-9)
• EPA Substance Registry System: 2,3-Dihydro-1-benzofuran-2-carboxylic acid(1914-60-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-51-22
• Safety Statements: 26-37/39
• Hazardous Substances Data: 1914-60-9(Hazardous Substances Data)

Usage

Description

2,3-Dihydro-1-benzofuran-2-carboxylic acid is an organic compound with the chemical formula C10H8O3. It is a white solid and serves as a crucial starting material in the synthesis of various derivatives with potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2,3-Dihydro-1-benzofuran-2-carboxylic acid is used as a starting material for the synthesis of (dihydro)benzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives. These derivatives have shown potential as anticancer agents, making this compound an important component in the development of novel treatments for cancer.
The compound's role in the synthesis of anticancer agents highlights its significance in the pharmaceutical industry, where it contributes to the creation of new drugs that can help combat various types of cancer.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 495, 1987 DOI: 10.1002/jhet.5570240236

InChI:InChI=1/C9H8O3/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-4,8H,5H2,(H,10,11)

Upstream product

• 108-95-2 phenol 
• 1746-13-0 allyl phenyl ether 
• 66158-96-1 2-hydroxymethyl-1H-2,3-dihydrobenzofuran 
• 1745-81-9 o-Allylphenol 
• 111080-49-0 o-(ethoxycarbonylmethoxy)benzyl chloride 
• 111080-48-9 ethyl 2-[2-(hydroxymethyl)phenoxy]acetate 
• 90-02-8 salicylaldehyde 
• 41873-61-4 ethyl (2-formylphenoxy)acetate 
• 43119-53-5 ethyl 2,3-dihydro-1-benzofuran-2-carboxylate 
• 496-41-3 Benzofuran-2-carboxylic acid 

Downstream Products

• 93885-44-0 2-methyl-2,3-dihydrobenzofuran-2-carboxylic acid 
• 89197-35-3 2-(2-phenethyl-2,3-dihydro-2-benzofuranyl)-2-imidazoline 
• 89197-32-0 efaroxan 
• 66673-55-0 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-53-8 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-54-9 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-52-7 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-51-6 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-oxo-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-50-5 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-oxo-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 57537-75-4 2,3-Dihydrobenzo[b]furan-2-carboxamide 
• 885069-03-4 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid 
• 27347-32-6 2,3-dihydrobenzofuran-2-carbonyl chloride 
• 89197-66-0 2-phenethyl-2,3-dihydrobenzofuran-2-carboxylic acid 
• 111080-50-3 2,3-dihydro-2-ethylbenzofurancarboxylic acid 

Relevant articles and documents

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Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB

With the aim of developing novel scaffolds as anticancer agents and inhibitors of NF-κB activity, 60 novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives (1a-s, 2a-k, 3a-s, and 4a-k) were designed and synthesized from the reference lead compound KL-1156, which is an inhibitor of NF-κB translocation to the nucleus in LPS-stimulated RAW 264.7 macrophage cells. The novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxamide derivatives exhibited potent cytotoxic activities (measured by the sulforhodamine B assay) at low micromolar concentrations against six human cancer cell lines: ACHN (renal), HCT15 (colon), MM231 (breast), NUGC-3 (gastric), NCI-H23 (lung), and PC-3 (prostate). In addition, these compounds also inhibited LPS-induced NF-κB transcriptional activity. The +M effect and hydrophobic groups on the N-phenyl ring potentiated the anticancer activity and NF-κB inhibitory activity, respectively. However, according to the results of structure-activity relationship studies, only benzofuran-2-carboxylic acid N-(4′-hydroxy)phenylamide (3m) was the lead scaffold with both an outstanding anticancer activity and NF-κB inhibitory activity. This novel lead scaffold may be helpful for investigation of new anticancer agents that act through inactivation of NF-κB.

Fused bicyclic carboxamide derivatives and methods of their use

Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.