146276-26-8

Basic information

• Product Name: ((E)-BUT-1-EN-3-YNYL)-BENZENE
• Synonyms: ((E)-BUT-1-EN-3-YNYL)-BENZENE
• CAS NO: 146276-26-8
• Molecular Formula: C₁₀H₈
• Molecular Weight: 128.17052
• Mol File: 146276-26-8.mol
• Article Data: 48

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ((E)-BUT-1-EN-3-YNYL)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: ((E)-BUT-1-EN-3-YNYL)-BENZENE(146276-26-8)
• EPA Substance Registry System: ((E)-BUT-1-EN-3-YNYL)-BENZENE(146276-26-8)

Safety Data

• Hazardous Substances Data: 146276-26-8(Hazardous Substances Data)

Usage

Description

((E)-BUT-1-EN-3-YNYL)-BENZENE, also known as (E)-But-1-en-3-ynyl-benzene or ethyl phenyl acetylene, is a chemical compound with the formula C10H10. It is a colorless liquid with a strong, floral odor and is commonly used as a building block in the synthesis of other organic compounds. ((E)-BUT-1-EN-3-YNYL)-BENZENE is highly flammable and should be handled with care, as it is known to be irritating to the eyes, skin, and respiratory system. Additionally, it is considered a potential environmental hazard due to its potential to bioaccumulate in aquatic organisms and persist in the environment. Proper safety protocols must be followed when working with this compound.

Uses

Used in Chemical Synthesis Industry:
((E)-BUT-1-EN-3-YNYL)-BENZENE is used as a building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable intermediate in the development of new and innovative products.
Used in Fragrance Industry:
Due to its strong, floral odor, ((E)-BUT-1-EN-3-YNYL)-BENZENE is used as a fragrance ingredient in the perfumery and cosmetics industry. It contributes to the creation of complex and pleasant scents in various personal care products.
Used in Research and Development:
((E)-BUT-1-EN-3-YNYL)-BENZENE is utilized in research and development settings to study its properties, reactivity, and potential applications in various fields. This includes exploring its use in the development of new materials, catalysts, and chemical processes.

Upstream product

• 80605-26-1 4-bromo-4-phenyl-1-butyne 
• 275-51-4 azulene 
• 14371-10-9 (E)-3-phenylpropenal 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 214491-15-3 (E)-(4-iodobut-1-en-3-yn-1-yl)benzene 
• 185038-94-2 ((1E)-4-bromobuta-1,3-dien-1-yl)benzene 
• 58335-31-2 1,3-dilithiopropyne 
• 100-52-7 benzaldehyde 
• 17975-54-1 (Z)-3-methyl-4-((E)-3-phenylallylidene)isoxazol-5(4H)-one 
• 98749-52-1 4-phenyl-1-(triphenylphosphoranylidene)-(3E)-buten-2-one 
• 78980-65-1 cinnamoyl(ethoxycarbonyl)methylene(triphenyl)phosphorane 
• 29070-69-7 ((1Z,3E)-4-Ethylsulfanyl-buta-1,3-dienyl)-benzene 
• 38002-48-1 E/Z-(4-phenylbut-3-ene-1-inyl)trimethyl-silane 
• 103-64-0 bromostyrene 

Downstream Products

• 42457-28-3 (E)-3-Methyl-5-(2-phenylethenyl)isoxazole 
• 935-01-3 (Z)-1-phenylbuten-3-yne 
• 116156-20-8 (1E,5E)-1,6-diphenylhexa-1,5-dien-3-yne 
• 1203605-80-4 (E)-2-oxo-4-phenyl-N-p-tolylbut-3-enamide 
• 1260102-52-0 C₁₅H₁₀O₂ 
• 1260102-54-2 C₁₅H₁₀OS 
• 1260102-40-6 (E)-1,5-diphenylpent-4-en-2-yn-1-one 
• 1260102-46-2 (E)-5-phenyl-1-(4-methylphenyl)pent-4-en-2-yn-1-one 
• 1260102-48-4 (E)-1-(4-chlorophenyl)-5-phenylpent-4-en-2-yn-1-one 
• 1260102-44-0 C₁₈H₁₄O 
• 1260102-50-8 C₂₁H₁₄O 
• 1609959-00-3 (E)-N-phenyl-2-(phenylthio)-2-styryl-N-tosylpent-4-enamide 

Relevant articles and documents

Addition and cyclization reactions in the thermal conversion of hydrocarbons with an enyne structure, 4: Formation and rearrangements of bicyclic C10H8 aromatics from 1-phenyl-1-buten-3-yne

The thermal conversion of 1-phenyl-1-buten-3-yne (1) into the cycloisomerization products naphthalene (2), azulene (3), and 1-methylene-1H-indene (4) has been studied at temperatures between 550 and 1000°C, a reaction time of approximately 0.3 s at 13 Tor

Synthesis of bis(alk-3-en-1-ynyl)benzene with either E- or Z-configuration via a one-pot three-component coupling reaction and its optical properties

A convenient, efficient and stereoselective synthesis of a range of bis(alk-3-en-1-ynyl)benzenes with E- and Z-configuration is described. The protocol involves Cu-mediated cross-coupling reaction of (E)- and (Z)-alk-1-enyldisiamylboranes with (trimethyls

Double cycloaromatization of (Z,Z)-deca-3,7-diene-1,5,9-triyne: Evidence for the intermediacy and diradical character of 2,6-didehydronaphthalene

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Probing E/Z isomerization on the C10H8 potential energy surface with ultraviolet population transfer spectroscopy

The excited-state dynamics of phenylvinylacetylene (1-phenyl-1-buten-3-yne, PVA) have been studied using laser-induced fluorescence spectroscopy, ultraviolet depletion spectroscopy, and the newly developed method of ultraviolet population transfer spectroscopy. Both isomers of PVA (E and Z) show a substantial loss in fluorescence intensity as a function of excitation energy. This loss in fluorescence was shown to be due to the turn-on of a nonradiative process by comparison of the laser-induced fluorescence spectrum to the ultraviolet depletion spectrum of each isomer, with a threshold 600 cm -1 above the electronic origin in Z-PVA and 1000 cm-1 above the electronic origin in E-PVA. Ab initio and density functional theory calculations have been used to show that the most likely source of the nonradiative process is from the interaction of the ππ* state with a close lying πσ* state whose minimum energy structure is bent along the terminal CCH group. Ultraviolet population transfer spectroscopy has been used to probe the extent to which excited-state isomerization is facilitated by the interaction with the πσ* state. In ultraviolet population transfer spectroscopy, each isomer was selectively excited to vibronic levels in the S1 state with energies above and below the threshold for fluorescence quenching. The ultraviolet-excited populations are then recooled to the zero point levels using a reaction tube designed to constrain the supersonic expansion and increase the collision cooling capacity of the expansion. The new isomeric distribution was detected in a downstream position using resonant-2-photon ionization spectroscopy. From these spectra, relative isomerization quantum yields were calculated as a function of excitation energy. While the fluorescence quantum yield drops by a factor of 50-100, the isomerization quantum yields remain essentially constant, implying that the nonradiative process does not directly involve isomerization. On this basis, we postulate that isomerization occurs on the ground-state potential energy surface after internal conversion. In these experiments, the isomerization to naphthalene was not observed, implying a competition between isomerization and cooling on the ground-state potential energy surface.

A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes

Alkynes R-C≡CH were obtained in good yield through a one-pot procedure by a sequence of reactions starting from a Wittig-type condensation of the aldehydes RCHO with the ylide derived from dibromomethyltriphenylphosphonium bromide 5. The same reactions could also be used to prepare the intermediate dibromoalkenes RCH=CBr2, and in certain cases, the bromoalkynes R-C≡CBr.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.