14374-45-9

Usage

Type of compound

Alkyne
1-Phenyl-1-heptyne is an alkyne compound, characterized by the presence of a carbon-carbon triple bond in its structure.

Usage

Organic synthesis and pharmaceutical production
1-PHENYL-1-HEPTYNE is utilized in organic synthesis and for the production of various chemicals and pharmaceuticals.

Physical appearance

Clear liquid
1-Phenyl-1-heptyne is a clear liquid, which means it does not have any color or suspended particles.

Odor

Slightly sweet
The compound has a slightly sweet odor, which may be noticeable at certain concentrations.

Melting point

-4°C
The melting point of 1-Phenyl-1-heptyne is -4°C, indicating the temperature at which it transitions from a solid to a liquid state.

Hazardous nature

Potential health and environmental risks
1-Phenyl-1-heptyne is considered a hazardous substance due to its potential risks to human health and the environment. It should be handled with caution and proper safety measures.

InChI:InChI=1/C13H16/c1-2-3-4-5-7-10-13-11-8-6-9-12-13/h6,8-9,11-12H,2-5H2,1H3

Upstream product

• 591-50-4 iodobenzene 
• 628-71-7 1-Heptyne 
• 57718-14-6 (7-iodohept-1-yn-1-yl)benzene 
• 693-02-7 hex-1-yne 
• 91787-30-3 2-phenylsulphonyl-1-phenylhept-1-ene 
• 693-25-4 n-pentylmagnesium bromide 
• 209912-23-2 1-(2-phenylethynyl)-1H-1,2,3-benzotriazole 
• 627885-28-3 dimethyl-(1-heptynyl)silanol 
• 108-86-1 bromobenzene 
• 17763-67-6 Phenyl triflate 
• 56651-44-6 1,1-bis-phenylsulfanyl-pentane 
• 24378-05-0 methyl phenylethynyl sulfone 
• 92078-65-4 (7-bromohept-1-yn-1-yl)benzene 
• 628-77-3 1,5-diiodopentane 

Downstream Products

• 1671-75-6 Heptanophenone 
• 10201-59-9 (Z)-hept-1-en-1-ylbenzene 
• 141527-73-3 (Z)-1-phenyl-2--1-heptene 
• 141527-74-4 (E)-1-phenyl-2--1-heptene 
• 118724-16-6 Co{(C₆H₅)C₂(C₅H₁₁)}{P(CH₃)3}3⁽¹⁺⁾*B(C₆H₅)4^(1-)=Co{(C₆H₅)C₂(C₅H₁₁)}{P(CH₃)3}3B(C₆H₅)4 
• 92543-29-8 WO(OC(CH₃)3)4(C₄H₈O) 
• 1448169-60-5 (E)-2'-(1-phenylhex-1-en-2-yl)[1,1'-biphenyl]-2-amine 
• 1448169-61-6 C₂₄H₂₅N 
• 1618681-28-9 (3-ethylcyclopent-1-ene-1,2-diyl)dibenzene 
• 1078-71-3 heptylbenzene 
• 10201-58-8 (E)-1-heptenylbenzene 

Relevant academic research and scientific papers

In situ stabilization of Pd0-nanoparticles into the nanopores of modified Montmorillonite: Efficient heterogeneous catalysts for Heck and Sonogashira coupling reactions

In situ generation of Pd0-nanoparticles into the nanopores of modified Montmorillonite and their catalytic performance in carboncarbon bond formation namely Heck and Sonogashira reactions, have been carried out. The modification of Montmorillonite was carried out by activating with H 2SO4 under controlled conditions for generating nanopores on the surface, which act as a 'Host' for Pd0-nanoparticles and was prepared by loading of K2PdCl4 metal precursor through incipient wetness impregnation technique followed by reduction with hydrazine hydrate. Powder-XRD, SEM-EDX, TEM, N2 adsorption, XPS, etc. analyses were carried out to characterize the stabilized nanoparticles as well as the supports. TEM study reveals that Pd0-nanoparticles of size below 10 nm were evenly distributed on the support and exhibit face centered cubic (fcc) lattice. The supported metal nanoparticles serve as efficient heterogeneous catalyst for the Heck coupling reaction in which the vinylation of aryl halides with olefins result cross-coupling products with maximum 96% isolated yield and >99% trans selectivity while in the alkynylation of aryl halides with terminal alkynes, i.e. in Sonogashira coupling reaction, a maximum of 94% isolated yield with 100% selectively cross-coupling products were observed. The nanocatalysts could be recycled and reused several times without significant loss of their catalytic activities.

Titanocene(ll)-promoted, one-pot, three-component coupling of thioacetals, alkynyl sulfones, and carbonyl compounds: Highly stereoselective formation of ferf-homopropargyl alcohols

Titanocene alkylidene complexes, generated by desulfurizative titanation of thioacetals with Cp2Ti[P(OEt)3J2, reacted with alkynyl methyl sulfones to produce organotitanium species, which gave tert-homopropargyl alcohols with high diastereoselectivity on treatment with aromatic and α,β-unsaturated ketones.

A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide

A new Pd/MgLa mixed oxide is found to be an efficient catalyst for the Sonogashira reaction of aryl iodides, bromides and even activated chlorides in the absence of a copper salt.

Catalytic reduction of phenyl-conjugated acetylenic halides by nickel(I) salen: Cyclization versus coupling

Cyclic voltammetry and controlled-potential electrolysis were employed to study the catalytic reduction of five phenyl-conjugated haloalkynes by nickel(I) salen electro-generated at carbon cathodes in dimethylformamide containing tetramethylammonium tetrafluoroborate. Electrocatalytic reduction of 7-bromo- and 7-iodo-1-phenyl-1-heptyne affords the carbocyclic product, benzylidenecyclohexane, in up to 41 % yield, whereas under similar conditions reduction of 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne gives benzylidenecyclobutane and benzylidenecycloheptane, respectively, in very low yield (≤1 %). Dimers, alkynes, and alkenynes are other products formed from the phenyl-conjugated haloalkynes. Dimers (diphenylalkadiynes) derived from 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne are obtained in yields ranging from 85 to 93 %, whereas 1,14-diphenyltetradeca-1,13-diyne (the dimer produced from 7-halo-1-phenyl-1-heptyne) is found in yields of 45-51 %. To account for the formation of the various products, a mechanistic scheme that involves phenyl-conjugated alkynyl radicals arising from nickel(I) salen catalyzed cleavage of the carbon-halogen bond of each substrate was formulated. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.

Synthesis of trisubstituted alkenes by Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters

A method for Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters was developed. The reaction has a broad substrate scope. This hydroalkylation shows excellent regio-and stereo-selectivity. This method enables readily available starting materials to be used to access a range of cyano-substituted single-configuration trisubstituted alkenes. These are valuable feedstock chemicals and are widely used in synthetic and medicinal chemistry.

Synthesis of a Cellulosic Pd(salen)-Type Catalytic Complex as a Green and Recyclable Catalyst for Cross-Coupling Reactions

Abstract: A green recyclable cellulose-supported Pd(salen)-type catalyst was synthesized through sequential three steps: chlorination with thionyl chloride, modification by ethylenediamine, and the formation of Schiff base with salicylaldehyde to immobilize palladium chloride through multiple binding sites. This novel heterogeneous cellulosic Pd(salen)-type catalytic complex was fully characterized by FT-IR, SEM, TEM, XPS, ICP-AES and TG. The traditional cross-coupling chemistry, such as Suzuki, Heck, Sonogashira, Buchwald–Hartwig amination and etherification, was then investigated in the presence of the above cellulose-palladium nanoparticle. Studies have shown that the synthesized catalyst shows high activity and efficiency for all types of transformations, providing the corresponding carbon–carbon or carbon–heteroatom coupling products in a general and mild manner. Furthermore, the catalyst demonstrates high to excellent yields and is easily recycled by simple filtration for up to twelve cycles without any significant loss of catalytic activity. Graphic Abstract: [Figure not available: see fulltext.]

PALLADIUM ACYCLIC DIAMINOCARBENE COMPLEXES AS PRECATALYSTS FOR HIYAMA COUPLING AND THE TANDEM ONE-POT FLUORIDE FREE HIYAMA COUPLING/CYCLIZATION FOR THE SYNTHESIS OF BIOLOGICALLY RELEVANT

The present invention provides Acyclic diaminocarbene complex of formula (I): Wherein, M is palladium; X is monoanionic ligand selected from Cl, Br or I; Where R1 is different from R2; R1 is selected from the group consisting of alkyl or aryl, each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms; R2 is selected from the group consisting of alkyl, or aryl each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms. The said palladium diamino carbine complex of the present invention are particularly useful as catalyst from Hiyama cross-coupling reaction.

Photoredox/Cobalt Dual Catalysis for Visible-Light-Mediated Alkene-Alkyne Coupling

Dual photoredox transition-metal catalysis has recently emerged as a powerful tool for making synthetically challenging carbon-carbon bonds under milder reaction conditions. Herein, we report on the visible-light-mediated controlled generation of low-valent cobalt catalyst without the need for a metallic reductant. It enabled C-C bond formation via ene-yne coupling at room temperature. The generality of this dual catalysis is demonstrated via the creation of sizable molecular diversity with the accommodation of several functional groups.

Ferrocenyl bisoxazoline as an efficient non-phosphorus ligand for palladium-catalyzed copper-free Sonogashira reaction in aqueous solution

Pd(OAc)2-catalyzed Sonogashira coupling reactions of alkynes and a variety of aryl halides with 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene as an efficient non-phosphorus ligand under copper-free conditions are presented. The main advantages over previous methodologies include low catalyst loading (0.2 mol% Pd(OAc)2 and 0.4 mol% ferrocenyl bisoxazoline ligand are sufficient for these coupling reactions), less problematic reaction medium (water–dimethylformamide) and more convenient operation (no requirement for nitrogen protection).