59292-71-6

Basic information

• Product Name: 5-Benzofurancarboxaldehyde, 4-hydroxy-
• Synonyms: 5-Benzofurancarboxaldehyde, 4-hydroxy-;4-hydroxybenzofuran-5-carbaldehyde
• CAS NO: 59292-71-6
• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14
• Mol File: 59292-71-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 60 °C(Solv: water (7732-18-5))
• Boiling Point: 172.7°C at 760 mmHg
• Flash Point: 58.3°C
• Appearance: /
• Density: 1.392g/cm³
• Vapor Pressure: 0.984mmHg at 25°C
• Refractive Index: 1.7
• PKA: 7.53±0.50(Predicted)
• CAS DataBase Reference: 5-Benzofurancarboxaldehyde, 4-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzofurancarboxaldehyde, 4-hydroxy-(59292-71-6)
• EPA Substance Registry System: 5-Benzofurancarboxaldehyde, 4-hydroxy-(59292-71-6)

Safety Data

• Hazardous Substances Data: 59292-71-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6O3/c10-5-6-1-2-8-7(9(6)11)3-4-12-8/h1-5,11H

Upstream product

• 59292-65-8 5-hydroxymethylene-6,7-dihydrobenzofuran-4(5H)-one 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 487-56-9 karanjic acid 
• 5369-62-0 (+/-)-3,3-dimethyloxirane-2-carboxaldehyde 
• 162794-47-0 5-hydroxymethylene-4,5,6,7-tetrahydrobenzofuran-4-one enol form 
• 480-97-7 4-hydroxybenzofuran 

Relevant articles and documents

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

Synthesis of 2,3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, xanthoarnol, and avicenol A. Biomimetic syntheses of angelicin and psoralen

(Chemical Equation Presented) We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure α,β-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.