14496-24-3

Basic information

• Product Name: furan-3,4-diyldimethanol
• Synonyms: furan-3,4-diyldimethanol;3,4-Bis(hydroxymethyl)furan;3,4-Furandimethanol;3,4-Furandiylbismethanol;Furan-3,4-dimethanol;Einecs 238-505-5;3,4-Bis(hydroxymethyl)furan 98%;[4-(hydroxymethyl)furan-3-yl]methanol
• CAS NO: 14496-24-3
• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.12592
• EINECS: 238-505-5
• Mol File: 14496-24-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 137.4°C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.248 g/mL at 25 °C
• Vapor Pressure: 5.21mmHg at 25°C
• Refractive Index: 1.542
• PKA: 13.88±0.10(Predicted)
• CAS DataBase Reference: furan-3,4-diyldimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: furan-3,4-diyldimethanol(14496-24-3)
• EPA Substance Registry System: furan-3,4-diyldimethanol(14496-24-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 14496-24-3(Hazardous Substances Data)

Usage

Uses

3,4-Furandimethanol has been used as a reactant in the preparation of N-[(benzimidazolyl)methyl]aminotetrahydroquinoline derivatives as CXCR4 antagonists that are potent inhibitors of T tropic (X4) HIV-1 replication.

InChI:InChI=1/C6H8O3/c7-1-5-3-9-4-6(5)2-8/h3-4,7-8H,1-2H2

Upstream product

• 693-93-6 4-methyloxazole 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 172043-66-2 7-oxa-norborn-2-ene-2,3-dicarboxylic acid diethyl ester 
• 30614-73-4 3,4-furan-dimethanol diacetate 
• 30614-77-8 diethyl 3,4-furandicarboxylate 
• 4282-33-1 dimethyl 3,4-furandicarboxylate 

Downstream Products

• 30614-73-4 3,4-furan-dimethanol diacetate 
• 109807-80-9 3,4-bis-benzoyloximethyl-furan 

Relevant articles and documents

Synthesis of the core framework of the cornexistins by intramolecular Nozaki-Hiyama-Kishi coupling

A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor.

Synthetic studies on the cornexistins: Synthesis of (±)-5-epi- hydroxycornexistin

The synthesis of 5-epi-hydroxycornexistin (44), a diastereoisomer of the herbicidal natural product hydroxycornexistin (2) has been completed. Palladium mediated sp2-sp3 coupling of the stannane 25 and the chloride 31 and ring-closing metathesis of the resulting diene 32 has been used to construct the tricyclic lactone 34a, which possesses the nine-membered carbocyclic core found in the natural product, in good yield. The synthesis of 5-epi-hydroxycornexistin (44) has established the feasibility of using a furan as precursor for the cyclic anhydride unit present in the natural product and has demonstrated the viability of other late-stage transformations that will be used to prepare hydroxycornexistin (2). The 2008 Royal Society of Chemistry.

A symmetry-based formal synthesis of zaragozic acid A

A symmetry-based strategy for the synthesis of the zaragozic acids is reported. Two enantioselective dihydroxylations were used to establish the absolute configuration of a C2 symmetric intermediate. Noteworthy transformations include a group-selective lactonization, which accomplished an end-differentiation of a pseudo-C2 symmetric intermediate. Late stage protecting group adjustments and oxidations accomplished a formal synthesis of zaragozic acid A.