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

• 122-00-9 para-methylacetophenone 
• 67-56-1 methanol 
• 91347-88-5 1-(4-methylphenyl)-1-cyclobutene 
• 79756-91-5 2-methyl-4-(4-methylphenyl)-3-butyn-2-ol 
• 624-31-7 4-tolyl iodide 
• 4301-14-8 acetylenemagnesium bromide 
• 460-12-8 Butadiyne 
• 108-88-3 toluene 
• 478556-98-8 C₄H₄Ir(P(C₆H₅)3)2COCCC₆H₄CH₃ 
• 1493-13-6 trifluorormethanesulfonic acid 
• 75-05-8 acetonitrile 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 593-53-3 Methyl fluoride 
• 536-74-3 phenylacetylene 

Downstream Products

• 93021-70-6 1-phenyl-3-(p-tolyl)prop-2-yn-1-ol 
• 139623-30-6 diphenyl[(4-methylphenyl)ethynyl]phosphane 
• 139016-38-9 1-methyl-4-(penta-1,2,4-trienyl)benzene 
• 139016-35-6 1-methyl-4-(pent-4-en-1-yn-1-yl)benzene 
• 139016-36-7 1-Methyl-4-((Z)-pent-3-en-1-ynyl)-benzene 
• 139016-36-7 1-Methyl-4-((E)-pent-3-en-1-ynyl)-benzene 
• 69374-88-5 4,4'-Di-n-octoxydiphenyldiacetylen 
• 69374-89-6 1,4-Bis<4-(decyloxy)phenyl>-1,3-butadiyne 
• 69374-90-9 1,4-Bis<4-(tetradecyloxy)phenyl>-1,3-butadiyne 
• 60512-43-8 1-(p-Tolylethynyl)cyclopropanol 
• 51270-89-4 1-(1-bromoethenyl)-4-methylbenzene 
• 26653-38-3 1-(buta-1,2-dien-1-yl)-4-methylbenzene 
• 219517-81-4 (E)-1-(1,2-diiodovinyl)-4-methylbenzene 
• 123770-66-1 1-{4-[2-(4-methylphenyl)ethynyl]phenyl}ethanone 

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.

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.

BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording Tetrahydroquinolines

An efficient BF3·OEt2-mediated propargyl alcohol rearrangement/[1,5]-hydride transfer/cyclization cascade for the synthesis of tetrahydroquinoline derivatives has been described. The substituents adjacent to triple bonds play an important role in the formation of ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products of formal trans-carbofluorination of internal alkynes. This method provides a rapid access to diverse heterocycles in moderate to excellent yields.