4200-06-0

Basic information

• Product Name: 1-ETHYNYL-4-PHENOXYBENZENE
• Synonyms: 1-ETHYNYL-4-PHENOXYBENZENE;1-ETHYNYL-4-(METHYLTHIO)-BENZENE;4'-PHENOXYPHENYL ACETYLENE;1-Ehynyl-4-phenoxybenzene;(4-Phenyloxyphenyl)ethyne;1-Ethynyl-4-phenoxybenzene 97%;1-ethynyl-4-(methylsulfanyl)benzene
• CAS NO: 4200-06-0
• Molecular Formula: C₁₄H₁₀O
• Molecular Weight: 194.23
• Product Categories: Alkynes;Organic Building Blocks;Terminal
• Mol File: 4200-06-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 284℃ (decomposition)
• Boiling Point: 90-95 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.074 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.131mmHg at 25°C
• Refractive Index: n20/D 1.6060(lit.)
• CAS DataBase Reference: 1-ETHYNYL-4-PHENOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYNYL-4-PHENOXYBENZENE(4200-06-0)
• EPA Substance Registry System: 1-ETHYNYL-4-PHENOXYBENZENE(4200-06-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41-43
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4200-06-0(Hazardous Substances Data)

Usage

Description

1-Ethynyl-4-phenoxybenzene is an organic compound characterized by the presence of an ethynyl group (a triple-bonded carbon chain) attached to a benzene ring, with a phenoxy group (an oxygen atom bonded to a benzene ring) at the para position. This unique molecular structure endows it with specific chemical properties that make it a versatile building block in organic synthesis.

Uses

Used in Organic Synthesis:
1-Ethynyl-4-phenoxybenzene is used as a key intermediate in the Sonogashira coupling reactions, which are palladium-catalyzed cross-coupling reactions between a terminal acetylene and an aryl or vinyl halide in the presence of a copper(I) co-catalyst. This reaction is a powerful tool in the synthesis of various conjugated molecules, including natural products, pharmaceuticals, and functional materials.
Used in the Preparation of 1-Vinyl-4-Phenoxybenzene:
1-Ethynyl-4-phenoxybenzene may be used as a precursor in the preparation of 1-vinyl-4-phenoxybenzene, a compound with potential applications in the synthesis of polymers, pharmaceuticals, and other organic compounds. The conversion from the ethynyl to the vinyl group can be achieved through selective hydrogenation or other chemical transformations, providing access to a broader range of chemical structures and functionalities.

InChI:InChI=1/C9H8S/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3

Upstream product

• 2974-94-9 4-phenoxyiodobenzene 
• 52446-51-2 2-(4-phenyloxyphenyl)ethyl alcohol 
• 1245913-04-5 trimethyl((4-phenoxyphenyl)ethynyl)silane 
• 101-55-3 4-Bromodiphenyl ether 
• 67-36-7 4-phenoxy benzaldehyde 
• 871592-08-4 1-(2,2-Dibromo-vinyl)-4-phenoxy-benzene 
• 5031-78-7 4-phenoxyacetophenone 
• 17541-02-5 2-Methyl-4-(4-phenoxy-phenyl)-but-3-yn-2-ol 

Downstream Products

• 325793-46-2 2-(4-phenoxy-phenylethynyl)-benzothiazole 
• 77384-56-6 1,2-bis(4-phenoxyphenyl)ethyne 
• 1133204-96-2 2-(4-phenoxyphenyl)-3H-indol-3-one-N-oxide 
• 1458695-35-6 2,4-bis(4-phenoxyphenyl)-6H-furo[2,3-b]pyran-6-one 
• 1394797-24-0 (Z)-4,4,5,5-tetramethyl-2-(4-(phenoxy)styryl)-1,3,2-dioxaborolane 
• 1400576-22-8 methyl 2,4-dimethyl-5-(4-phenoxyphenyl)furan-3-carboxylate 
• 60319-82-6 phenoxy-4-prop-1-ynylbenzene 
• 1391056-60-2 C₂₃H₁₉NO₄ 
• 1391056-87-3 C₂₂H₁₅NO₄ 
• 1391056-80-6 C₂₄H₂₁NO₄ 
• 1383663-36-2 (Z)-2-methyl-1-(4-phenoxystyryl)-1H-indole 
• 1374353-99-7 C₂₈H₃₃NO₃SSi 

Relevant articles and documents

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.

Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions

The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.

BTK INHIBITOR

Provided are a series of BTK inhibitors, and specifically disclosed are a compound, pharmaceutically acceptable salt thereof, tautomer thereof or prodrug thereof represented by formula (I), (II), (III) or (IV).