1665-35-6

Basic information

• Product Name: 2-Phenyl-5-ethylnylthiophene
• Synonyms: 2-Phenyl-5-ethylnylthiophene
• CAS NO: 1665-35-6
• Molecular Formula: C₁₂H₈S
• Molecular Weight: 184.26
• Mol File: 1665-35-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 308.1°Cat760mmHg
• Flash Point: 103.2°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.00127mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: 2-Phenyl-5-ethylnylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-5-ethylnylthiophene(1665-35-6)
• EPA Substance Registry System: 2-Phenyl-5-ethylnylthiophene(1665-35-6)

Safety Data

• Hazardous Substances Data: 1665-35-6(Hazardous Substances Data)

Usage

Uses

2-Ethynyl-5-phenylthiophene is used as a reactant in the palladium-?catalyzed syntheses of naturally occurring acetylenic thiophenes and related compounds.

InChI:InChI=1/C12H8S/c1-2-11-8-9-12(13-11)10-6-4-3-5-7-10/h1,3-9H

Upstream product

• 1257985-10-6 triisopropyl((5-phenylthiophen-2-yl)ethynyl)silane 
• 71-43-2 benzene 
• 5370-19-4 5-iodothiophene-2-carbaldehyde 
• 13781-37-8 2-iodo-5-phenylthiophene 
• 825-55-8 2-phenylthiophene 
• 19163-21-4 5-phenylthiophene-2-carboxaldehyde 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 1204-82-6 2-Phenyl-5-(1'-propynyl)-thiophene 
• 94742-70-8 2-phenyl-5-(3-buten-1-ynyl)thiophen 

Relevant articles and documents

Palladium-catalyzed direct alkynylation of thiophenes with halosilylacetylenes

Silylethynylthiophenes were obtained from palladium-catalyzed alkynylation of various thiophenes with 1-halo-2-silylacetylenes. The α-position of thiophenes was alkynylated with high regioselectivity. The terminal silyl groups of products could be replaced by several functional groups.

PALLADIUM-CATALYZED SYNTHESES OF NATURALLY-OCCURRING ACETYLENIC THIOPHENS AND RELATED COMPOUNDS

5-(3-buten-1-ynyl)-2,2'-bithienyl (1a), a natural product first isolated from Tagetes roots which shows nematicidal and photo-induced fungicidal activity, and 2-phenyl-5-(3-buten-1-ynyl) thiophen (1b) have been synthesized using two different methods.The first one (Method A) involves the palladium-catalyzed cross-coupling of vinyl bromide with the Grignard reagents derived from 5-ethynyl-2,2'-bithienyl (6a) and 2-ethynyl-5-phenylthiophen (6b).The second method (Method B) utilizes the coupling reaction of vinyl bromide with 6a and 6b, respectively, in the presence of a catalytic amount of (PPh3)4Pd and CuI.Such reaction, which was carried out under phase-transfer conditions employing BnEt3N(+)Cl(-) as phase transfer agent and 2.5N aq NaOH as base, has been also employed to prepare a large number of heterocyclic acetylene derivatives including some naturally-occuring compounds.The experimental conditions of Method B allow also the direct production of heterocyclic acetylene derivatives (1) starting from 1-alkynyltrimethylsilanes (5) and organic halides (2).