2144-40-3

Basic information

• Product Name: CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN
• Synonyms: ((2R,5S)-Tetrahydrofuran-2,5-diyl)diMethanol;(5-HydroxyMethyl-tetrahydro-furan-2-yl)-Methanol;(cis-Tetrahydrofuran-2,5-diyl)dimethanol;erythro-Hexitol,2,5-anhydro-3,4-dideoxy-
• CAS NO: 2144-40-3
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Mol File: 2144-40-3.mol
• Article Data: 86

Chemical Properties

• Melting Point: 130.5 °C(Solv: benzene (71-43-2); ethyl ether (60-29-7))
• Boiling Point: 261.6°Cat760mmHg
• Flash Point: 112°C
• Appearance: /
• Density: 1.13g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.14±0.10(Predicted)
• CAS DataBase Reference: CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN(2144-40-3)
• EPA Substance Registry System: CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN(2144-40-3)

Safety Data

• Hazardous Substances Data: 2144-40-3(Hazardous Substances Data)

Usage

Description

CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN, also known as 2,5-Bishydroxymethyl Tetrahydrofuran, is a tetrahydrofuran compound substituted with two hydroxymethyl groups. It is an oily liquid substance that is soluble in chloroform, ethyl acetate, and methanol. CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN is potentially useful as a fragment for the synthesis of small molecules, nucleoside derivatives, and materials.

Uses

Used in Organic Synthesis:
CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN is used as an intermediate in organic synthesis for the creation of various small molecules, nucleoside derivatives, and materials. Its unique structure and solubility properties make it a valuable component in the development of new chemical compounds and substances.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN is used as a key building block for the synthesis of complex drug molecules. Its versatility in organic synthesis allows for the development of novel therapeutic agents with potential applications in various medical fields.
Used in Chemical Research:
CIS-2,5-BISHYDROXYMETHYL-TETRAHYDROFURAN is also utilized in chemical research for the exploration of new reaction pathways and the development of innovative synthetic methods. Its unique properties and reactivity contribute to the advancement of chemical science and the discovery of new compounds with potential applications in various industries.

Upstream product

• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 1472-01-1 cis-2,5-bis(methoxycarbonyl)tetrahydrofuran 
• 99974-69-3 cis-tetrahydro-furan-2,5-dicarboxylic acid diethyl ester 
• 1883-75-6 2,5-bis-(hydroxymethyl)furan 
• 592-42-7 1,5-Hexadien 
• 108-24-7 acetic anhydride 
• 119873-51-7 (+/-)-[(2S,5R)-tetrahydrofuran-2,5-diyl]bis(methyl) diacetate 
• 60-29-7 diethyl ether 
• 2240-81-5 cis-tetrahydrofuran-2,5-dicarboxylic acid 
• 4282-32-0 furan-2,5-dicarboxylic acid dimethyl ester 
• 20221-46-9 meso-2,5-dihydroxy-adipic acid 
• 1888-89-7 1,5-hexadiene diepoxide 
• 67-56-1 methanol 
• 10551-58-3 5-acetoxymethyl-2-furaldehyde 

Downstream Products

• 6973-62-2 2,5-Bis-acetoxymethyl-tetrahydro-furan 
• 1472-00-0 cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate 
• 123292-07-9 (20R,23S)-31,33,34,35-tetrakis(phenylmethoxy)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene 
• 122383-79-3 (20R,23S)-14,29-Dimethyl-4-<2,4-dinitro-6-(trifluoromethyl)anilino>-31,33,34,35-tetraethoxy-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene 
• 122110-95-6 (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene 
• 36842-37-2 Dimethyl-((2S,5S)-5-methyl-tetrahydro-furan-2-ylmethyl)-amine 
• 119943-83-8 cis-Hydroxymethyl-2-methoxycarbonyl-tetrahydrofuran 
• 119943-82-7 (-)-cis-5-(hydroxymethyl)tetrahydrofuran-2-carboxylic acid 
• 96479-19-5 (2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester 
• 20221-50-5 1,2,5,6-hexanetetrol 
• 280-13-7 8-oxa-3-aza-bicyclo[3.2.1]octane 
• 99969-71-8 2-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-ethanol 
• 165879-74-3 tetrahydrofuran 2,5-dimethanol di p-toluenesulphonate 
• 108-95-2 phenol 

Relevant articles and documents

A highly efficient procedure for ruthenium tetroxide catalyzed oxidative cyclizations of 1,5-dienes

We report a highly efficient procedure for the oxidative cyclization of 1,5-dienes, which generally allows for high yields and selectivities. A solid-supported terminal oxidant and a finely tuned solvent mixture have both been identified as critical facto

Perruthenate ion. Another metal oxo species able to promote the oxidative cyclisation of 1,5-dienes to 2,5-disubstituted cis-tetrahydrofurans

Perruthenate ion, from tetrapropylammonium perruthenate (TPAP), in the presence of tetrabutylammonium periodate (TBAPI) as reoxidant catalyses the stereospecific and stereoselective oxidative cyclisation of 1,5-dienes to cis-2,5-disubstituted tetrahydrofu

Formic Acid-Assisted Selective Hydrogenolysis of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran over Bifunctional Pd Nanoparticles Supported on N-Doped Mesoporous Carbon

Biomass-derived 5-hydroxymethylfurfural (HMF) is regarded as one of the most promising platform chemicals to produce 2,5-dimethylfuran (DMF) as a potential liquid transportation fuel. Pd nanoparticles supported on N-containing and N-free mesoporous carbon materials were prepared, characterized, and applied in the hydrogenolysis of HMF to DMF under mild reaction conditions. Quantitative conversion of HMF to DMF was achieved in the presence of formic acid (FA) and H2 over Pd/NMC within 2 h. The reaction mechanism, especially the multiple roles of FA, was explored through a detailed comparative study by varying hydrogen source, additive, and substrate as well as by applying in situ ATR-IR spectroscopy. The major role of FA is to shift the dominant reaction pathway from the hydrogenation of the aldehyde group to the hydrogenolysis of the hydroxymethyl group via the protonation by FA at the C-OH group, lowering the activation barrier of the C?O bond cleavage and thus significantly enhancing the reaction rate. XPS results and DFT calculations revealed that Pd2+ species interacting with pyridine-like N atoms significantly enhance the selective hydrogenolysis of the C?OH bond in the presence of FA due to their high ability for the activation of FA and the stabilization of H?.

Preparation method 2 and 5 - tetrahydrofuran dimethanol

The preparation method of 2-5 - tetrahydrofuran dimethanol (THFDM) comprises the following steps: mixing a solvent containing 5 - hydroxymethylfurfural raw material with a catalyst, and reacting in an atmosphere containing hydrogen to obtain the 2 and 5 - tetrahydrofuran dimethanol. The purity of 5 - hydroxymethyl furfural raw material is 90 - 99%. The catalyst comprises a carrier and an active component. The active component is loaded on the carrier. The active component includes a noble metal element. The carrier comprises a carbon material. The method is simple in synthesis process, and has a great application prospect in the field of a plurality of fields, especially degradable materials.

Metal-free photocatalytic aerobic oxidation of biomass-based furfural derivatives to prepare γ-butyrolactone

Efficient catalytic oxidative C-C bond cleavage with dioxygen is useful and challenging to prepare oxygenated fine chemicals from biomass. Herein, we report a catalytic strategy for the preparation of γ-butyrolactone (GBL) by photocatalytic oxidation of tetrahydrofurfuryl alcohol (THFA), tetrahydrofurfuric acid (THFCA), or other furfural derivatives at room temperature under visible-light irradiation. Metal-free mesoporous graphitic carbon nitride was used as the photocatalyst and O2was used as the oxidant. The effects of various semiconductor catalysts, light sources with different wavelengths, and the reaction time on the photocatalytic oxidation of THFA to GBL were separately investigated. Furthermore, the reaction mechanism was investigated through serious control experiments and the reaction pathway was investigated through density functional theory (DFT) calculations.