70283-74-8

Basic information

• Product Name: 4,6-DECADIYN-1,10-DIOL
• Synonyms: 4,6-DECADIYN-1,10-DIOL;4,6-DECADIYNE-1,10-DIOL;TIMTEC-BB SBB008876
• CAS NO: 70283-74-8
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 70283-74-8.mol

Chemical Properties

• Melting Point: 45.5 °C
• Boiling Point: 45-47°C
• Flash Point: 181.3 °C
• Appearance: gray purple crystals or powder
• Density: 1.07 g/cm³
• Vapor Pressure: 8.45E-07mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: 4,6-DECADIYN-1,10-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DECADIYN-1,10-DIOL(70283-74-8)
• EPA Substance Registry System: 4,6-DECADIYN-1,10-DIOL(70283-74-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 70283-74-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4,6-DECADIYN-1,10-DIOL is used as a chemical intermediate for the synthesis of various organic compounds due to its reactive diol and diacetylene functional groups.
Used in Material Science:
4,6-DECADIYN-1,10-DIOL is used as a monomer for the preparation of polydiacetylene-based materials, which are valued for their potential applications in chemical sensing, biomedical devices, and optoelectronic devices. The unique properties of these materials, such as their sensitivity to environmental changes and their ability to form thin films, make them suitable for these high-tech applications.
Used in Pharmaceutical Research:
4,6-DECADIYN-1,10-DIOL is studied for its potential antitumor properties, with ongoing research exploring its effects on tumor cells and its possible integration into cancer treatment strategies.
Used in Antibacterial Applications:
4,6-DECADIYN-1,10-DIOL is also being investigated for its antibacterial properties, with potential use in the development of new antimicrobial agents to combat resistant bacterial strains.

InChI:InChI=1/C10H14O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,5-10H2

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 55501-48-9 5-bromopent-4-yn-1-ol 
• 629-05-0 n-octyne 
• 3140-93-0 2,3-dibromothiophen 
• 536-74-3 phenylacetylene 
• 16218-28-3 2,7-diiodofluorene 
• 3001-15-8 4,4'-diiodobiphenyl 
• 629-89-0 1-octadecyne 
• 765-10-6 1-tetradecyne 
• 764-93-2 1-decyne 
• 700380-30-9 5-(benzyloxy)-1-(trimethylsilyl)pent-1-yn-3-ol 
• 887502-14-9 1,10-bis-benzyloxy-deca-4,6-diyne-3,8-diol 
• 90246-36-9 5-(benzyloxy)-1-pentyn-3-ol 

Downstream Products

• 112-47-0 1,10-Decanediol 
• 69284-59-9 4,6-decadiyn-1,10-diol bis-(p-toluenesulfonate) 
• 1363157-33-8 4,6-decadiyne-1,10-diyl bis[N-(3,4,5-trimethoxyphenyl)carbamate] 
• 1363157-32-7 4,6-decadiyne-1,10-diyl bis[N-(3,4,5-tridodecyloxyphenyl)carbamate] 

Relevant articles and documents

Efficient one-step synthesis of bis-spiroketals from diynediols by π-Lewis acid-catalyzed hydroalkoxylation/hydration

Spiroling out of control: An efficient one-step synthesis of 5-5-5, 5-5-6, and 6-5-6 bis-spiroketals from 4,6-diyne-1,n-diols and 5,7-diyne-1,n-diols has been developed with good yields. A mixture of cis- and trans-bis-spiroketals were generally obtained from each substrate and the isolated cis- and trans-bis-spiroketals undergo interconversion to reach their equilibrium composition (see scheme).

Synthesis and Evaluation of a Series of Bis(pentylpyridinium) Compounds as Antifungal Agents

A series of bis(4-pentylpyridinium) compounds with a variety of spacers between the pyridinium headgroups was synthesised, and the antifungal activity of these compounds was investigated. Lengthening the alkyl spacer between the pentylpyridinium headgroups from 12 to 16 methylene units resulted in increased antifungal activity against C. neoformans and C. albicans, but also resulted in increased hemolytic activity and cytotoxicity against mammalian cells. However, inclusion of an ortho-substituted benzene ring in the centre of the alkyl spacer resulted in decreased cytotoxicity and hemolytic activity, while maintaining antifungal potency. Replacement of the alkyl and aromatic-containing spacers by more hydrophilic ethylene glycol groups resulted in a loss of antifungal activity. Some of the compounds inhibited fungal PLB1 activity, but the low correlation of this inhibition with antifungal potency indicates PLB1 inhibition is unlikely to be the predominant mode of antifungal action of this class of compounds, with preliminary studies suggesting they may act via disruption of fungal mitochondrial function.

Copper Catalysis for Selective Heterocoupling of Terminal Alkynes

A Cu-catalyzed selective aerobic heterocoupling of terminal alkynes is disclosed, which enables the synthesis of a broad range of unsymmetrical 1,3-diynes in good to excellent yields. The results disprove the long-held belief that homocouplings are exclusively favored in the Glaser-Hay reaction.

Recyclable Polystyrene-Supported Copper Catalysts for the Aerobic Oxidative Homocoupling of Terminal Alkynes

Polystyrene-supported copper(II) N,N,N′,N′-tetraethyldiethylenetriamine [Cu(II)-TEDETA] complexes were prepared by immobilization of TEDETA onto crosslinked polystyrene resin, followed by complexation with copper salts. The polystyrene-immobilized CuSOsu

Synthesis and solid-state polymerization of butadiyne derivatives with Trialkoxyphenylurethane groups

3,4,5-Trialkoxyphenyl isocyanate derivatives, in which alkoxy was dodecyloxy or methoxy, reacted with 4,6- decadiyn-1,10-diol and 5,7-dodecadiyn-1,12-diol, and four butadiyne derivatives with (N-trialkoxyphenyl)urethane groups were successfully synthesized. Their solid-state polymerization stimulated by UV or ￡-ray irradiation was investigated. All monomers in crystals were found to be polymerizable. However, conversion was different depending on the compounds. The derivatives from 5,7-dodecadiyn-1,12-diol showed better conversion, suggesting that they have more favorable monomer arrangement for the solid-state polymerization. Polymers of dodecyloxy derivatives could be partially dissolved in chloroform and they showed solvatochromism when hexane was added to the solution. As was expected from the structure of tridodecyloxyphenyl groups introduced, dodecyloxy derivatives gave organogels in various organic solvents in the concentration less than 2wt%. However, these gels could not be polymerized by UV irradiation, and the monomer alignment was found to be different between crystalline and gel states.

A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system

A simple copper promoting system CuI/NBS/DIPEA was first found to efficiently promote Glaser coupling reaction under ambient temperature. The alkynes with sensitive groups such as acetal and ketal, TBDMS, ester and amide could react smoothly to afford the

New irreversible thermochromic polydiacetylenes

New diacetylenic compounds are described. These compounds are unfunctionalised, monoalcohols, diols or monoesters and present irreversible thermochromic behaviour. When heated, these diynes change colour from blue to red in temperature ranging between -50 and +75 °C depending on chain lengths. A relationship between the number of atoms and the thermochromism temperature has been highlighted. Moreover, a mechanism of this thermochromic phenomenon is demonstrated based on Raman spectroscopy, ESR and solid NMR.

[1,3]-Transfer of chirality during the nicholas reaction in γ-benzyloxy propargylic alcohols

A highly regio- and stereoselective intramolecular [1.5]-hydrogentransfer process is described. Treatment of γ-benzyl-protccted Co 2(CO)6-α,γ-acetylenic diols with BF 3·OEt2 provides bis-homopropargylic alcohols. The reaction occurs within seconds, tolerates a wide range of functionalities, and provides good yields. When the ether group is located at a stereochemically defined carbon atom, the rearrangement occurs with high stereoselectivity, transferring the chirality of the carbinol center to the newly created stereocenter. The cleavage of the benzyloxy group is totally regioselective when additional benzyl ethers are present. The scope and limitations of this novel process in densely substituted substrates are evaluated, and possible competitive reactions and/or stereochemical influences are also described. A mechanism based on a highly ordered chair-like transition state substantiated by a theoretical study is also included.

Aliphatic acetylenic homocoupling catalyzed by a novel combination of AgOTs-CuCl2-TMEDA and its application for the solid-phase synthesis of bis-benzo[b]furan-linked 1,3-diynes

(Matrix presented) A novel catalytic system of AgOTs-CuCl 2-TMEDA is described for the homocoupling of aliphatic acetylenes on solid support. It is the first observation that AgI's activating triple bond could facilitate CuII/s

Pd-catalysed cross coupling of terminal alkynes to diynes in the absence of a stoichiometic additive

An efficient, room temperature procedure for the cross-coupling of a range of terminal alkynes, using standard Sonogashira cross-coupling conditions (Pd/Cu) is presented. At higher reaction temperatures, head-to-tail or head-to-head dimerisation affords 1,3- and 1,4-disubstituted enynes, respectively as minor products.