1129-65-3

Basic information

• Product Name: 1-PHENYL-1-HEXYNE
• Synonyms: TIMTEC-BB SBB008962;1-Hexyne, 1-phenyl-;1-hexyne,1-phenyl-;benzene,1-hexynyl-;Butylphenylacetylene;1-HEXYNYLBENZENE;1-PHENYL-1-HEXYNE;1-BUTYL-2-PHENYLACETYLENE
• CAS NO: 1129-65-3
• Molecular Formula: C₁₂H₁₄
• Molecular Weight: 158.24
• Product Categories: Acetylenes;Acetylenic Hydrocarbons having Benzene Ring
• Mol File: 1129-65-3.mol

Chemical Properties

• Boiling Point: 229-232 °C(lit.)
• Flash Point: 208 °F
• Appearance: /
• Density: 0.9 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0994mmHg at 25°C
• Refractive Index: n20/D 1.5349(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-PHENYL-1-HEXYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-1-HEXYNE(1129-65-3)
• EPA Substance Registry System: 1-PHENYL-1-HEXYNE(1129-65-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 1129-65-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Phenyl-1-hexyne is used as a starting material for the synthesis of various organic compounds due to its unique structure and reactivity. The selective hydrogenation, polymerization, and isomerization reactions of 1-phenyl-1-hexyne enable the production of a wide range of chemical products.
Used in Material Science:
1-Phenyl-1-hexyne can be used as a monomer in the synthesis of polymers and copolymers, which can have potential applications in various industries, such as plastics, coatings, and adhesives. The polymerization of 1-phenyl-1-hexyne by pentahalides of niobium and tantalum can lead to the formation of new polymeric materials with unique properties.
Used in Electrochemistry:
1-Phenyl-1-hexyne can be used in electrochemical processes, such as electrolytically induced, base-catalyzed isomerization, to produce other valuable compounds, like 1-phenyl-1,2-hexadiene. This can be useful in the development of new electrochemical methods for organic synthesis and the production of specialty chemicals.
Used in Catalyst Research:
The selective hydrogenation of 1-phenyl-1-hexyne over palladium catalysts supported on mesostructured silica can be used to study the properties and performance of catalysts in various chemical reactions. This can contribute to the development of more efficient and selective catalysts for industrial applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 3444, 1979 DOI: 10.1021/jo01333a049

InChI:InChI=1/C12H14/c1-2-3-4-6-9-12-10-7-5-8-11-12/h5,7-8,10-11H,2-4H2,1H3

Upstream product

• 80-44-4 n-butyl benzenesulfonate 
• 1004-22-4 (phenylethynyl)sodium 
• 693-03-8 n-butyl magnesium bromide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 542-69-8 1-iodo-butane 
• 6928-78-5 Bis(phenylethynyl)magnesium 
• 57718-12-4 (6-iodohex-1-yn-1-yl)benzene 
• 543-63-5 n-butylmercuric chloride 
• 3757-88-8 tributylstannylethynylbenzene 
• 122-56-5 tributyl borane 
• 546-67-8 lead(IV) tetraacetate 
• 536-74-3 phenylacetylene 
• 98-80-6 phenylboronic acid 
• 693-02-7 hex-1-yne 

Downstream Products

• 35010-25-4 methyl 2-phenylhexanoate 
• 34252-39-6 3-Hydroperoxy-1-phenyl-1-hexin 
• 240133-09-9 2-butyl-3-phenyl-2-cyclopenten-1-one 
• 942-92-7 caprophenone 

Relevant articles and documents

The Sonogashira Reaction in Ionic Liquids

The Sonogashira reaction of iodobenzene with phenylacetylene in several room temperature ionic liquids was studied. A regeneration of the catalytical system immobilized in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6) has been als

Copper-catalyzed coupling reaction of terminal alkynes with aryl- and alkenyliodonium salts

(Equation presented) The copper iodide-catalyzed cross-coupling of terminal alkynes with hypervalent iodonium salts was accomplished with Cul (10 mol %) and NaHCO3 (2 equiv) in DME/H2O (4:1) at room temperature for 30 min to afford arylalkynes or enynes under mild conditions.

Electrochemical Reduction and Intramolecular Cyclization of 6-Iodo-1-phenyl-1-hexyne at Vitreous Carbon Cathodes in Dimethylformamide

In dimethylformamide containing a tetraalkylammonium perchlorate, a cyclic voltammogram for reduction of 6-iodo-1-phenyl-1-hexyne at a glassy carbon electrode exhibits three prominent waves corresponding to cleavage of the carbon-iodine bond and to subsequent reductions of 1-phenyl-1-hexyne and benzylidenecyclopentane.At potentials for which only reduction of the carbn-iodine bond occurs, large-scale electrolytes of 6-iodo-1-phenyl-1-hexyne afford benzylidenecyclopentanone and 1-phenyl-1-hexyne; the yield of the carbocycle, averaging 36percent, is insensitive to potential, but the quantity of 1-phenyl-1-hexyne varies from 28 to 48percent as the potential is chosen to be more negative.In the presence of diethyl malonate as a proton donor, the quantity of benzylidenecyclopentane changes little, the yield of 1-phenyl-1-hexyne decreases, and substantial (>33percent) diethyl (1-phenyl-1-hexyn-6-yl)malonate is obtained.With 1,1,1,3,3,3-hexafluoroisopropyl alcohol as proton source, the yield of benzylidenecyclopentane increases to approximately 60percent, whereas the quantity of 1-phenyl-1-hexyne decreases somewhat.It appears that each of the major hydrocarbon products is formed via a combination of one- and two-electron processes.

A convenient high activity catalyst for the Sonogashira coupling of aryl bromides

A mixture of Na2PdCl4, CuI and (t-Bu) 3PH+BF4- (molar ratio 4:3:8) dispersed in H2N(i-Pr)2 Br can be used as a "single source" precatalyst for the Sonogashira coupling of aryl bromides with various aryl- and alkylacetylenes in HN(i-Pr)2 solvent. Arylacetylenes require just 0.005 mol % of Pd catalyst at 80°C, with TOFs ranging between 3,200 and 10,000 h-1.

Efficient coupling reactions of lithium alkynyl(triisopropoxy)borates with aryl halides: Application to the antifungal terbinafine synthesis

Thermally stable lithium alkynyl(triisopropoxy)borates were reacted with several aryl halides in the presence of palladium catalysts to give the corresponding cross-coupling products in excellent yields. The present methodology has been successfully appli

A copper-free Sonogashira reaction using nickel ferrite as catalyst in water

The Sonogashira reaction using nickel ferrite nanoparticles as catalyst and under copper-free conditions was investigated in water as a green solvent. Various types of aryl and alkyl halides were successfully coupled with phenyl acetylene under the optimized reaction conditions with very good to excellent yields at a short time. The catalyst is easily recoverable and can be reused for several runs with a good turnover number.

A novel method of C-C bond formation via phenylation of terminal acetylenes by triphenylbismuth difluoride

Terminal acetylenes readily undergo phenylation by Ph3BiF2 in the presence of catalytic amounts of CuCl affording phenyl substituted acetylenes.

Rhodium-catalyzed synthesis of indenols by regioselective coupling of alkynes with ortho-carbonylated arylboronic acids

A rhodium/diene-catalyzed regioselective synthesis of indenols has been developed through the coupling of alkynes with ortho-carbonylated arylboronic acids. These reactions proceed under mild conditions in uniformly high yield and regioselectivity. The re

Palladium-catalyzed R(sp3)-Zn/R(sp)-SnBu3 oxidative cross-coupling

A novel bond formation through oxidative cross-coupling with desyl chloride as the oxidant has been investigated. The coupling can be carried out under mild conditions. The Csp3-center carbon was involved even in the presence of a β-H, and up to 90% of the desired cross-coupling product was obtained with the secondary Csp3-center substrate. Georg Thieme Verlag Stuttgart.

Organic functionalization of mesopore walls in hierarchically porous zeolites

Mesopore walls of hierarchically meso-/microporous zeolites (MFI, BEA and LTA) are covered with silanol groups, so that the zeolites can be functionalized with various organic groups via silylation; the organic-functionalized hierarchical zeolites exhibit