765-10-6

Usage

Uses

1-Tetradecyne is used in the chemical industry for a variety of addition reactions involving alkynes. These reactions include hydrogenation, halogenation, hydrohalogenation, and hydration, among others. The triple bond in 1-Tetradecyne allows for the formation of new compounds and functional groups, making it a versatile building block in organic synthesis.
Used in Chemical Synthesis:
1-Tetradecyne is used as a reactant in chemical synthesis for the production of various organic compounds. Its triple bond enables the formation of new carbon-carbon and carbon-heteroatom bonds, which can be further modified to create a wide range of products.
Used in Polymer Synthesis:
In the field of polymer science, 1-Tetradecyne can be used as a monomer in the synthesis of polymers with specific properties. The triple bond can be polymerized to form polyacetylenes or copolymers with other monomers, leading to materials with unique characteristics.
Used in Pharmaceutical Industry:
1-Tetradecyne may also find applications in the pharmaceutical industry, where it can be used as a starting material for the synthesis of bioactive compounds or as a building block for the development of new drugs.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 891, 1975 DOI: 10.1021/ja00837a034Synthetic Communications, 5, p. 331, 1975 DOI: 10.1080/00397917508062086

InChI:InChI=1/C14H26/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h1H,4-14H2,2H3

Upstream product

• 6064-46-6 1-bromo-tetradec-1-ene 
• 1066-26-8 sodium acetylide 
• 143-15-7 1-dodecylbromide 
• 68-12-2 N,N-dimethyl-formamide 
• 35216-11-6 7-tetradecyne 
• 6064-45-5 1,2-dibromotetradecane 
• 57160-02-8 1-chloro-2-ethoxy-tetradecane 
• 70277-75-7 lithium acetylide 
• 29552-15-6 4-chloro-2-methylbut-3-yn-2-ol 
• 4292-19-7 1-Iodododecane 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1120-36-1 1-tetradecene 
• 136689-90-2 trimethyl(tetradec-1-ynyl)silane 
• 73501-38-9 (±)-tetradec-1-yn-3-ol 

Downstream Products

• 2834-00-6 2-pentadecyn-1-ol 
• 638-60-8 2-tetradecyne 
• 117710-70-0 1,1,1-trifluorohexadec-3-yn-2-one 
• 132330-38-2 (E/Z)-1-Phenylselenododec-1-ene 
• 87742-52-7 tetradec-1-yn-1-yl(phenyl)sulfane 
• 159458-29-4 5-dodecyl-3-(phenylmethyl)isoxazole 
• 194861-77-3 (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 225936-86-7 4-methoxyphenyl 5-octadecyn-(2E)-enyl ether 
• 753020-03-0 (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol 
• 947747-24-2 C₅₉H₇₁N₃O₈ 
• 947747-31-1 C₄₄H₅₃N₃O₃ 
• 947747-48-0 C₄₄H₅₃N₃O₃ 
• 947747-25-3 (2S,3S,4R)-2-azido-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol 
• 947747-26-4 C₆₆H₇₉N₃O₈ 

Relevant academic research and scientific papers

Efficient synthesis of akolactone A via Pd-catalyzed carbonylation

The first synthesis of (+)- and (-)-akolactone A is described by using Pd-catalyzed carbonylation. A comparison of the optical rotation of both enantiomers of akolactone A and the natural compound suggests that the absolute configuration at the 4-position of akolactone A is R.

Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester

Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium-allenylidene complexes may work as key reactive intermediates.

Formation of conjugated polynaphthalene via Bergman cyclization

A series of enediyne containing chiral phthalimides were synthesized through Sonogashira coupling reactions. These enediynes were then subjected to thermal Bergman cyclization under vacuum. Polynaphthalenes with pendant chiral groups were obtained and characterized using GPC, IR spectroscopy, NMR spectroscopy, UV-Vis spectroscopy, and photoluminescence analysis. Under properly optimized conditions, the chirality of chiral directing group was maintained according to CD spectra of final products. After removal of chiral directing groups, weak CD signals representative of main chain chirality were visible. Further modification of the structure of the enediyne compounds will facilitate the synthesis of chiral polynaphthalene through this rather simple way. Extension of the Bergman cyclization to polymer chemistry is promising in the construction of novel polymers with rigid polyarene back-bones.

Modular approach to the synthesis of unsaturated 1-monoacyl glycerols

A modular synthesis of unsaturated 1-monoacylglycerols (1) from cis-1-iodo-1-alkenes [cis-RCH=CHI] and unsaturated carboxylic acids [CH 2=CH(CH2)nCO2H] is described. The method revolves around a Suzuki coupling to establish olefin geometry.

Reaction of Grignard compounds with 4-chloro-2-methyl-3-butyn-2-ol in Diethyl Ether equivalents

Reactions of RMgX · THF complexes with 4-chloro-2-methyl-3-butyn-2-ol in aromatic hydrocarbons were studied. The complexes formed by arylmagnesium halides require the presence of anisole for the reaction to occur. 4-Chloro-2-methyl-3-butyn-2-ol can be synthesized by reaction of 2-methyl-3-butyn-2-ol with sodium hypochloride in the two-phase system water-benzene.

Photopolymerization in Monolayers of an Amphiphilic Diacetylene Derivative containing a Ferrocene Group

The photopolymerization of heptadeca-2,4-diynylferrocenecarboxylate in the monolayer on a water surface was investigated by studying pressure-area isotherms and electronic spectra; the polymerization behaviour was found to depend markedly on the molecular packing in the monolayer.

PROTOTROPIC ISOMERIZATION OF ACETYLENIC HYDROCARBONS AND ALCOHOLS UNDER THE INFLUENCE OF LITHIUM 2-AMINOETHYLAMIDE IN ETHYLENEDIAMINE

The system containing lithium 2-aminoethylamide in ethylenediamine is an effective system for the production of acetylenic hydrocarbons and alcohols with a terminal triple bond.As a result of prototropic isomerization in this system 5-dodecyne, 4-tridecyne, 7-tetradecyne, 2-heptyn-1-ol, 2-nonyn-1-ol, and 2-undecyn-1-ol gave high yields of the corresponding isomers with a terminal triple bond, i.e., 1-dodecyne, 1-tridecyne, 1-tetradecyne, 6-heptyn-1-ol, 8-nonyn-1-ol, and 10-undecyn-1-ol.The synthesis of the long-chain alcohol 8,10-heneicosadiyn-1-ol was realized from the compounds containing a triple bond.

Alkyne isomerization reagents: mixed alkali metal amides

Addition of sodium and potassium alkoxides, particularly potassium tert-butoxide, to the lithium salts of either 1,2-diaminoethane or 1,3-diaminopropane afford alkyne isomerization reagents that effect triple bond migration to the end of a methylene chain under milder conditions and in higher yield than do previously reported reagents.