3031-68-3

Basic information

• Product Name: 2,4-HEXADIYNE-1,6-DIOL
• Synonyms: 2,4-Hexadiynediol;Diacetylene glycol;TIMTEC-BB SBB008793;1,6-DIHYDROXY-2,4-HEXADIYNE;2,4-HEXADIENE-1,6-DIOL;2,4-HEXADIYN-1,6-DIOL;2,4-HEXADIYNE-1,6-DIOL;hexa-2,4-diyne-1,6-diol
• CAS NO: 3031-68-3
• Molecular Formula: C₆H₆O₂
• Molecular Weight: 110.11
• EINECS: 221-210-0
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Diyne Compounds (LB Films);Functional Materials;LB Films
• Mol File: 3031-68-3.mol
• Article Data: 59

Chemical Properties

• Melting Point: 109-112 °C
• Boiling Point: 292.1 °C at 760 mmHg
• Flash Point: 151 °C
• Appearance: /
• Density: 1.234 g/cm³
• Vapor Pressure: 0.0002mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 12.26±0.10(Predicted)
• BRN: 773791
• CAS DataBase Reference: 2,4-HEXADIYNE-1,6-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-HEXADIYNE-1,6-DIOL(3031-68-3)
• EPA Substance Registry System: 2,4-HEXADIYNE-1,6-DIOL(3031-68-3)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-22-24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• F: 4.5-8
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 3031-68-3(Hazardous Substances Data)

Usage

Uses

2,4-Hexadiyne-1,6-diol may be used as a starting material in the synthesis of thiarubrine A (an antibiotic). It may also be used to synthesize disodium salt of 2,4-hexadiyne 1,6-disulfate (HDDS).

General Description

2,4-Hexadiyne-1,6-diol can be prepared from propargyl alcohol. 2,4-Hexadiyne-1,6-diol readily undergoes polymerization when heated under vacuum or inert gas atmosphere.

InChI:InChI=1/C6H6O2/c7-5-3-1-2-4-6-8/h7-8H,5-6H2

Upstream product

• 50-00-0 formaldehyd 
• 460-12-8 Butadiyne 
• 107-19-7 propargyl alcohol 
• 33324-62-8 1,6-bis-(1-butoxy-ethoxy)-hexa-2,4-diyne 
• 1725-82-2 3-iodo-2-propyn-1-ol 
• 821-10-3 1,4-Dichloro-2-butyne 
• 7732-18-5 water 
• 536-74-3 phenylacetylene 
• 622-79-7 benzyl azide 
• 629-89-0 1-octadecyne 
• 765-10-6 1-tetradecyne 
• 765-03-7 1-dodecyne 
• 629-74-3 hexadec-1-yne 
• 764-93-2 1-decyne 

Downstream Products

• 109511-56-0 5,5'-bis-hydroxymethyl-1,1'-diphenyl-1H,1'H-[4,4']bi[1,2,3]triazolyl 
• 629-11-8 1,6-hexanediol 
• 107550-83-4 (2E,4E)-hexa-2,4-diene-1,6-diol 
• 16260-59-6 1,6-dichlorohexa-2,4-diyne 
• 24996-68-7 1,6-bis-(2-carboxy-benzoyloxy)-hexa-2,4-diyne 
• 63621-96-5 (2Z,4Z)-Hexa-2,4-diene-1,6-diol 
• 73097-71-9 2,4-hexadiyne-1,6-bis(m-tolyluretane) 
• 85523-38-2 2-phenylthio-2-hexen-4-yne-1,6-diol 
• 54981-67-8 deca-2t,8t-diene-4,6-diynedioic acid dimethyl ester 
• 65367-63-7 (2E,8Z)-deca-2,8-diene-4,6-diynedioic acid dimethyl ester 
• 110-54-3 hexane 
• 111-27-3 hexan-1-ol 
• 24996-65-4 1,6-bis(benzoyloxy)hexadiyne-2,4 
• 165404-84-2 tert-Butyl-dimethyl-(6-phenoxymethyl-[1,2]dithiin-3-ylmethoxy)-silane 

Relevant articles and documents

Synthesis of 1,3-diynes using palladium-copper catalyses

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Mechanistic investigation and further optimization of the aqueous Glaser-Hay bioconjugation

The Glaser-Hay bioconjugation has recently emerged as an efficient and attractive method to generate stable, useful bioconjugates with numerous applications, specifically in the field of therapeutics. Herein, we investigate the mechanism of the aqueous Glaser-Hay coupling to better understand optimization strategies. In doing so, it was identified that catalase is able to minimize protein oxidation and improve coupling efficiency, suggesting that hydrogen peroxide is produced during the aqueous Glaser-Hay bioconjugation. Further, several new ligands were investigated to minimize protein oxidation and maximize coupling efficiency. Finally, two novel strategies to streamline the Glaser-Hay bioconjugation and eliminate the need for secondary purification have been developed.

Glaser coupling reaction in supercritical carbon dioxide

It is demonstrated for the first time that Glaser coupling can be carried out smoothly in supercritical carbon dioxide using a solid base (NaOAc) instead of amines.

Noncatalytic, solvent-free thermal formation of cyclic trimers using 1,6-bis(acyloxymethyl)hexa-2,4-diyne derivatives

The thermal reactivity of diacetylenes in the liquid phase was studied extensively to elucidate the cooperative mechanism of polymerization.

Glaser oxidative coupling in ionic liquids: An improved synthesis of conjugated 1,3-diynes

Terminal alkynes undergo oxidative-coupling smoothly in the presence of the CuCl-TMEDA catalytic system in hydrophobic [bmim]PF6 ionic liquid under aerobic conditions to produce 1,3-diynes in excellent yields under mild conditions. The substrates, alkynes, show enhanced reactivity and selectivity in ionic liquids (ILs). The recovery of the catalyst is facilitated by the hydrophobic nature of the [bmim]PF6 ionic liquid.

In the optically-multiplexed-

A method for optical super-multiplexing using polyynes to provide enhanced images from stimulated Raman microscopy is disclosed. In some exemplary embodiments, the polyynes are organelle-targeted or spectral barcoded. Imaging can be enhanced by using the polyynes to image whole live cells or specific organelles within live cells. The polyynes can also be used in optical data storage (i.e., encoding) and identification (i.e., decoding) applications.

Diacetylene-Based C 2h-Symmetric Monomers for Two-Dimensional-Polymer Synthesis

Two linear monomers with two terminal photoreactive groups (anthracene or maleimide) embedded in a diacetylene skeleton were synthesized for two-dimensional-polymer synthesis. Both of them were crystallized and their single-crystal structures were solved. It was found that the size of terminal groups can be critical for diacetylene's arrangement. The crystal structure of dimaleimide monomer revealed that maleimide groups strongly stacking in antiparallel and the photo-induced [2+2] cycloaddition of stacked maleimides was preliminary studied.