766-97-2

Basic information

• Product Name: 4-Ethynyltoluene
• Synonyms: BENZENE, 1-ETHYNYL-4-METHYL-;1-ETHYNYL-4-METHYLBENZENE;5-ETHYNYLTOLUENE;4'-METHYLPHENYL ACETYLENE;4-METHYLPHENYLACETYLENE;4-ETHYNYLTOLUENE;p-Methylphenylacetylene;P-ETHYNYLTOLUENE
• CAS NO: 766-97-2
• Molecular Formula: C₉H₈
• Molecular Weight: 116.16
• EINECS: 1533716-785-6
• Product Categories: Aromatic Compounds;pharmacetical;Miscellaneous Compounds;Acetylenes;Acetylenic Hydrocarbons;Liquid crystal intermediates
• Mol File: 766-97-2.mol
• Article Data: 80

Chemical Properties

• Melting Point: 168-170
• Boiling Point: 168-170 °C(lit.)
• Flash Point: 120 °F
• Appearance: Clear pale yellow/Liquid
• Density: 0.916 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.62mmHg at 25°C
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: Keep Cold
• Water Solubility: Insoluble in water.
• BRN: 969653
• CAS DataBase Reference: 4-Ethynyltoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethynyltoluene(766-97-2)
• EPA Substance Registry System: 4-Ethynyltoluene(766-97-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38
• Safety Statements: 16-26-27-36/37/39
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• RTECS: XT2570000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 766-97-2(Hazardous Substances Data)

Usage

Description

4-Ethynyltoluene is an organic compound characterized by the presence of an ethynyl group (a triple-bonded carbon chain) attached to a toluene molecule. It is a versatile building block in organic synthesis and has unique properties due to its ethynyl functional group.

Uses

Used in Organic Synthesis:
4-Ethynyltoluene is used as a key intermediate in the synthesis of various organic compounds, particularly in the formation of bis(bicyclic) products through the cycloaddition of alkynes to the AlN2C2 moiety. This process allows for the creation of complex molecular structures with potential applications in various fields.
Used in Liquid Crystals Industry:
4-Ethynyltoluene serves as an intermediate in the production of liquid crystals, which are essential components in display technologies such as LCD screens. Its unique molecular structure contributes to the development of liquid crystal materials with specific properties, enhancing their performance in electronic devices.

InChI:InChI=1/C9H8/c1-3-9-6-4-8(2)5-7-9/h1,4-7H,2H3

Upstream product

• 42107-37-9 α-chloro-p-methylstyrene 
• 624-31-7 4-tolyl iodide 
• 471-25-0 Propiolic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 74-86-2 acetylene 
• 1273578-50-9 N-benzyl-3-(4-methylphenyl)-2-propynylamine 
• 536-74-3 phenylacetylene 
• 16520-62-0 4-Phenyl-1-butyne 
• 693-02-7 hex-1-yne 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 52916-86-6 (2RS,3SR)-2,3-dibromo-3-(4-methylphenyl)propanoic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Downstream Products

• 128010-24-2 Se-(p-Tolylethynyl) selenobenzoate 
• 134261-81-7 2-(4-methylphenyl)-1,4-pentadiene 
• 25364-68-5 (E)-1-benzoyl-2-(4-methylphenyl)-1-etheneyl cyanide 
• 180585-48-2 (Z)-4-oxo-4-phenyl-2-(p-tolyl)but-2-enenitrile 
• 185520-93-8 p-Tolylethynyl-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 196599-47-0 5-(4-tolyl)penta-2,4-diyn-1-ol 
• 125951-08-8 (Z)-1-methyl-4-[2-(phenylsulfanyl)ethenyl]benzene 
• 125951-09-9 (E)-1-methyl-4-[2-(phenylsulfanyl)ethenyl]benzene 
• 253435-19-7 2-(2-(4-methylphenyl)ethynyl)-1-iodobenzene 
• 136612-72-1 (E)-1,4-di(4-methylphenyl)butenyne 
• 155129-02-5 1,1'-(3-methylene-1-propyne-1,3-diyl)bis(4-methylbenzene) 
• 189331-74-6 (Z)-4,4‘-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) 
• 200293-66-9 N-[4-[2-(4-Methylphenyl)ethynyl]phenylsulfonyl]-D-tryptophan methyl ester 
• 200293-69-2 N-[4-[2-(4-Methylphenyl)ethynyl]phenylsulfonyl]-D-valine t-butyl ester 

Relevant articles and documents

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes

Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.