765-10-6

Basic information

• Product Name: 1-TETRADECYNE
• Synonyms: 1-TETRADECYNE;TIMTEC-BB SBB008951;1-C14H26;1-Tetradecyne,tech.90%;1-TETRADECYNE: TECH., 90%;Dodecylacetylene;tetradec-1-yne;1-TETRADECYNE 98%
• CAS NO: 765-10-6
• Molecular Formula: C₁₄H₂₆
• Molecular Weight: 194.36
• EINECS: 212-139-6
• Product Categories: Acetylenes;Acetylenic Hydrocarbons
• Mol File: 765-10-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 2.51°C (estimate)
• Boiling Point: 132-134°C 14mm
• Flash Point: 132-134°C/14mm
• Appearance: colourless to light yellow liquid
• Density: 0.790 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0321mmHg at 25°C
• Refractive Index: n20/D 1.440
• Water Solubility: Not miscible with water. soluble in common organic solvents of low polarity
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, heavy metals, heavy metal salts.
• BRN: 1746546
• CAS DataBase Reference: 1-TETRADECYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TETRADECYNE(765-10-6)
• EPA Substance Registry System: 1-TETRADECYNE(765-10-6)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 765-10-6(Hazardous Substances Data)

Usage

Chemical Properties

colourless to light yellow liquid

Uses

1-Tetradecyne is used in addition reactions of alkynes like hydrogenation, halogenation, hydrohalogenation, hydration reactions and others.

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

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

Downstream Products

• 638-60-8 2-tetradecyne 
• 87742-52-7 tetradec-1-yn-1-yl(phenyl)sulfane 
• 159458-29-4 5-dodecyl-3-(phenylmethyl)isoxazole 
• 947747-24-2 C₅₉H₇₁N₃O₈ 
• 947747-31-1 C₄₄H₅₃N₃O₃ 
• 947747-48-0 C₄₄H₅₃N₃O₃ 
• 1192674-28-4 1-methoxy-4-[(1E)-tetradec-1-en-1-yl]benzene 
• 1229010-13-2 5,6-di(tetradec-1-ynyl)-2-((R)-1-phenylethyl)isoindoline 
• 2345-27-9 tetradecan-2-one 
• 596815-62-2 pentadeca-1,2-diene 
• 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 
• 753020-03-0 (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol 
• 225936-86-7 4-methoxyphenyl 5-octadecyn-(2E)-enyl ether 
• 194861-77-3 (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

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.

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.

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.