622-76-4

Basic information

• Product Name: 1-PHENYL-1-BUTYNE
• Synonyms: Ethylphenylacetylene;Phenylethylacetylene;1-Phenyl-1-butyne, 98+%;Benzene, 1-butynyl- (9CI);(1-Butadiynyl)benzene;1-(1-Butynyl)benzene;C6H5C≡CC2H5;1-Phenyl-1-butyne,1-Butynylbenzene
• CAS NO: 622-76-4
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 130.19
• EINECS: 210-752-3
• Product Categories: Acetylenes;Acetylenic Hydrocarbons having Benzene Ring
• Mol File: 622-76-4.mol

Chemical Properties

• Boiling Point: 73-75 °C4 mm Hg(lit.)
• Flash Point: 156 °F
• Appearance: /
• Density: 0.916 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.428mmHg at 25°C
• Refractive Index: n20/D 1.551(lit.)
• BRN: 1903397
• CAS DataBase Reference: 1-PHENYL-1-BUTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-1-BUTYNE(622-76-4)
• EPA Substance Registry System: 1-PHENYL-1-BUTYNE(622-76-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 622-76-4(Hazardous Substances Data)

Usage

Chemical Description

1-phenyl-1-butyne and 1-phenyl-1-propyne are acetylenic hydrocarbons, while n-butyllithium and methyllithium are alkyllithium reagents used for metallation.

Uses

Used in Chemical Research and Development:
1-Phenyl-1-butyne is used as a subject of study for the liquid-phase stereoselective hydrogenation of phenyl alkyl acetylenics at 298K and atmospheric pressure on Pd-supported catalysts. This application is crucial for understanding the behavior and potential applications of phenyl alkyl acetylenic compounds in various chemical processes.
Used in Catalyst Development:
1-Phenyl-1-butyne plays a role in the development of catalysts, specifically palladium particles incorporated into organophilic montmorillonite, for the liquid-phase hydrogenation process. This application is essential for enhancing the efficiency and selectivity of hydrogenation reactions in the chemical industry.
Used in Polymer Science:
1-Phenyl-1-butyne is used as a monomer in the copolymerization process with C60, a well-known fullerene. This application is significant for the development of new materials with unique properties and potential applications in various industries, such as electronics, energy storage, and nanotechnology.
Used in the Chemical Industry:
1-Phenyl-1-butyne is utilized as a reactant in various chemical reactions, particularly with alkali metals like sodium and potassium. This application is vital for the synthesis of different organic compounds and the advancement of the chemical industry.

InChI:InChI=1/C10H10/c1-2-3-7-10-8-5-4-6-9-10/h4-6,8-9H,2H2,1H3

Upstream product

• 107-00-6 but-1-yne 
• 591-50-4 iodobenzene 
• 134166-48-6 4-phenylbut-3-yn-2-amine 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 108-86-1 bromobenzene 
• 5963-77-9 pent-2-ynoic acid 
• 108-90-7 chlorobenzene 
• 3757-88-8 tributylstannylethynylbenzene 
• 925-90-6 ethylmagnesium bromide 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 
• 1007-32-5 benzyl ethyl ketone 

Downstream Products

• 129762-21-6 C₁₆H₁₅FS 
• 17204-78-3 3-Ethyl-4-phenyl-3-cyclobuten-1,2-dione 
• 345954-15-6 C₁₈H₂₀S₂ 
• 98793-38-5 C₁₆H₁₆S₂ 
• 22751-52-6 2,3-diphenylbenzo[b]thiophene 
• 4923-91-5 2,3-dimethylbenzothiophene 
• 73569-66-1 E-1,2-bismethylsulphonyl-1-phenylbut-1-ene 
• 73569-67-2 Z-1,2-bismethylsulphonyl-1-phenylbut-1-ene 
• 142232-53-9 N-<2-benzoyl-1-(4-methoxyphenyl)butyl>benzamide 
• 103835-21-8 2,5-Diethyl-3,6-diphenyl-1,4-dithiin-Radikalkation 
• 152959-30-3 (E)-1-bromo-1-phenyl-2-(benzenesulfonyl)but-1-ene 
• 94571-24-1 phenyl 2-(1-phenylbutyl) sulfone 
• 10540-29-1 tamoxifen 
• 66584-35-8 tamoxifen hydrochloride 

Relevant articles and documents

Elucidation of reaction process through β-halogen elimination in CuCN-mediated cyanation of (E)-1-bromo-2-iodoalkene

The previously unknown reaction process involved with metal-mediated β-halogen elimination is described, including a description of a vinylic Rosenmund-von Braun reaction of (E)-(1-bromo-2-iodobut-1-en-1-yl)benzene. We investigated the product structures on the basis of crystallographic analyses and revealed that copper cyanide would form bifurcated paths to deliver the isomeric mixtures.

A new method for the preparation of alkynes from vinyl triflates

Treatment of vinyl triflates with lithium diisopropylamide results in the selective formation of alkynes in moderate to high yields.

Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations

The Lewis acid-promoted generation of destabilized vinyl cations from β-hydroxy diazo ketones leads to an energetically favorable 1,2-shift across the alkene followed by an irreversible C-H insertion to give cyclopentenone products. This reaction sequence overcomes typical challenges of counter-ion trapping and rearrangement reversibility of vinyl cations and has been used to study the migratory aptitudes of nonequivalent substituents in an uncommon C(sp2) to C(sp) vinyl cation rearrangement. The migratory aptitude trends were consistent with those observed in other cationic rearrangements; the substituent that can best stabilize a cation more readily migrates. However, density functional theory calculations show that the situation is more complex. Selectivity in the formation of one conformational isomer of the vinyl cation and facial selective migration across the alkene due to an electrostatic interaction between the vinyl cation and the adjacent carbonyl oxygen work in concert to determine which group migrates. This study provides valuable insight into predicting migration preferences when applying this methodology to the synthesis of structurally complex cyclopentenones that are differentially substituted at the α and β positions.

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Palladium-catalyzed methylation of terminal alkynes

In this communication, a palladium-catalyzed procedure for the methylation of terminal alkynes has been developed. With N,N,N-trimethylbenzenaminium trifluoromethanesulfonate as the methyl source, various desired products were obtained in moderate to good yields. Both aromatic and aliphatic alkynes are applicable.

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.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

RETRACTED ARTICLE: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines

A mild and efficient strategy for decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) coupling of α,β-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.

Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive

Convenient access to diverse libraries of internal alkynes via decarboxylative Sonogashira reaction of alkynyl-carboxylic acids with iodoarenes, employing imidazolium-ILs as solvent, along with piperidine-appended imidazolium [PAIM][NTf2] as task-specific basic IL is demonstrated, without the need for any ligand or additive. The feasibility to perform these reactions by sequential one-pot iododediazoniation/decarboxylative Sonogashira reaction is also shown, and the scope of the methods is underscored by providing 29 examples. The potential for recycling and reuse of the IL solvent is also examined.