2935-44-6

Basic information

• Product Name: 2,5-Hexanediol
• Synonyms: HEXANEDIOL;2,5-HEXYLENE GLYCOL;2,5-HEXANEDIOL;2,5-DIHYDROXYHEXANE;Diisopropanol;Hexan-2,5-diol;hexane-2,5-diol;2,5-Hexanediol 3 M Solution
• CAS NO: 2935-44-6
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17
• EINECS: 220-910-3
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 2935-44-6.mol
• Article Data: 42

Chemical Properties

• Melting Point: 43°C
• Boiling Point: 216-218 °C(lit.)
• Flash Point: 215 °F
• Appearance: clear colorless to light yellow viscous liquid
• Density: 0.961 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00693mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.87±0.20(Predicted)
• Water Solubility: Soluble
• BRN: 1719248
• CAS DataBase Reference: 2,5-Hexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Hexanediol(2935-44-6)
• EPA Substance Registry System: 2,5-Hexanediol(2935-44-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: MO2275000
• TSCA: Yes
• Hazardous Substances Data: 2935-44-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow viscous liquid

Uses

2,5-Hexanediol is used as an organic chemical synthesis intermediate.

Definition

ChEBI: A glycol that is hexane substituted by hydroxy groups at positions 2 and 5.

InChI:InChI=1/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2

Upstream product

• 3031-66-1 3-hexyn-2,5-diol 
• 75-07-0 acetaldehyde 
• 74-86-2 acetylene 
• 94-36-0 dibenzoyl peroxide 
• 684-72-0 2,5-bis-trifluoroacetoxy-hexane 
• 67-63-0 isopropyl alcohol 
• 504-63-2 trimethyleneglycol 
• 60-29-7 diethyl ether 
• 1888-89-7 1,5-hexadiene diepoxide 
• 5194-51-4 (2E,4E)-hexa-2,4-diene 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 592-42-7 1,5-Hexadien 
• 691-78-1 Hexen-⁽⁵⁾-yl-⁽²⁾-trifluoracetat 
• 625-72-9 (R)-3-hydroxybutyric acid 

Downstream Products

• 1003-38-9 2,5-dimethyltetrahydrofuran 
• 37035-03-3 N-Phenyl-2,5-dimethylpyrrolidine 
• 41761-11-9 meso-2,5-dichlorohexane 
• 13275-18-8 rac-2,5-dichlorohexane 
• 54462-67-8 meso-2,5-dibromo-hexane 
• 24774-58-1 racem. 2,5-dibromo-hexane 
• 10299-35-1 2,5-Diacetoxy-hexan 
• 1757-42-2 3-methyl-cyclopentanone 
• 24200-03-1 2,5-bis-(4-nitro-benzoyloxy)-hexane 
• 110-13-4 2,5-hexanedione 
• 592-46-1 hexa-2,4-diene 
• 94844-84-5 4,7-dimethyl-2-phenyl-[1,3,2]dioxaborepane 
• 123826-85-7 5-(benzyloxy)hexan-2-ol 
• 59694-06-3 2,5-hexanediol monobenzoate 

Relevant articles and documents

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-CYCLOADDITION OF SINGLET OXYGEN TO CONJUGATED ACYCLIC HEXADIENES : EVIDENCE OF SINGLET OXYGEN INDUCED cistrans-ISOMERIZATION

Addition of singlet oxygen to trans,trans-2,4-hexadiene (1) occurs stereospecifically to give endoperoxide 2.With cis,trans-2,4-hexadiene (4), however, a mixture of diastereomeric endoperoxides, 2 + 5, is observed.Evidence of a singlet oxygen - induced cistrans - isomerization is gained by competitive Diels-Alder reaction of 4 with singlet oxygen/diethyl diazenedicarboxylate.

Support Effect of Ru Catalysts for Efficient Conversion of Biomass-Derived 2,5-Hexanedione to Different Products

Tuning the activity of supported metals by changing the properties of supports is a highly attractive strategy to realize some important reactions in biomass transformation. Herein, Ru nanoparticles supported on montmorillonite (MMT) and hydroxyapatite (HAP), denoted as Ru/MMT and Ru/HAP, were prepared. It was found that the activity of the Ru catalysts for different routes to convert biomass-derived 2,5-hexanedione (2,5-HD) could be controlled by the support materials. Ru/MMT was active for the synthesis of dimethyltetrahydrofuran from hydrogenation of 2,5-HD at 90 °C, while Ru/HAP showed excellent performance on the conversion of 2,5-HD into N-substituted tetrahydropyrroles at 30 °C via direct reductive amination. Systematic study revealed that the property of support materials influenced the activity of Ru/MMT and Ru/HAP for the different routes, affording different reaction pathways for conversion of 2,5-HD.

Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.

Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: Silyl species enable reactivity

Biomass derivatives are a class of oxygen-rich organic compounds, which can be selectively upgraded to various value-added molecules by partial or complete hydrogenation over metal catalysts. Here, we show that Cs2CO3, a low-cost commercial chemical, enables the selective reduction of dicarbonyl compounds including bio-derived carboxides to monohydric esters/amides, hydroxylamines or diols with high yields (82-99%) at room temperature using eco-friendly and equivalent hydrosilane as a hydride donor. The in situ formation of silyl ether enables the developed catalytic system to tolerate other unsaturated groups and permits a wide substrate scope with high selectivities. Spectroscopic and computational studies elucidate reaction pathways with an emphasis on the role of endogenous siloxane.