768-60-5

Basic information

• Product Name: 4-Ethynylanisole
• Synonyms: Benzene, 1-ethynyl-4-methoxy-;P-ETHYNYLANISOLE;1-ETH-1-YNYL-4-METHOXYBENZENE;1-ETHYNYL-4-METHOXYBENZENE;4-ETHYNYLANISOLE;4'-METHOXYPHENYL ACETYLENE;4-METHOXYPHENYLACETYLENE;Benzene, 1-ethynyl-4-methoxy- (9CI)
• CAS NO: 768-60-5
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.16
• Product Categories: Liquid Crystal intermediates;pharmacetical;Aromatics Compounds;Aromatics;Alkynes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Terminal
• Mol File: 768-60-5.mol
• Article Data: 197

Chemical Properties

• Melting Point: 28-29 °C(lit.)
• Boiling Point: 87-91 °C11 mm Hg(lit.)
• Flash Point: 180 °F
• Appearance: Clear colorless to deep yellow or brown/Liquid or Low Melting Solid
• Density: 1.019 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.563(lit.)
• Storage Temp.: Store Cold
• Solubility: Acetontrile (Slightly), Chloroform (Slightly)
• Water Solubility: Insoluble in water. Soluble in chloroform, acetone, dichloromethane, and methanol.
• Sensitive: Light Sensitive
• Stability: Light and Temperature Sensitive
• CAS DataBase Reference: 4-Ethynylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethynylanisole(768-60-5)
• EPA Substance Registry System: 4-Ethynylanisole(768-60-5)

Safety Data

• Hazard Codes: Xn,F
• Statements: 22
• Safety Statements: 24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• PackingGroup: II
• Hazardous Substances Data: 768-60-5(Hazardous Substances Data)

Usage

Description

4-Ethynylanisole is an organic compound characterized by its pale yellow oil appearance. It is known for its ability to form the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal, eliminating the need for creating an acetylide salt. This versatile compound is utilized in various chemical reactions and synthesis processes due to its unique properties.

Uses

1. Used in Pharmaceutical Industry:
4-Ethynylanisole is used as an intermediate for the synthesis of histamine H3-receptor antagonists, which are essential in the development of medications targeting various conditions, including allergies and cardiovascular diseases.
2. Used in Liquid Crystal Industry:
4-Ethynylanisole serves as an intermediate in the production of liquid crystals, which are crucial components in the manufacturing of display technologies, such as LCD screens.
3. Used in Chemical Synthesis:
4-Ethynylanisole is used as a reactant in the 1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes, a chemical reaction that affords functionalized cyclopentenes in good yields. This process is significant in the synthesis of various organic compounds.
4. Used in Luminescent Material Production:
4-Ethynylanisole is utilized to prepare its luminescent copper complex, which has potential applications in the development of advanced materials with unique optical properties.
5. Used in Photo Luminescent Material Synthesis:
4-Ethynylanisole is employed in the synthesis of photo luminescent 1,2-dihydrophosphinines through a [4 + 2] cycloaddition reaction, contributing to the development of materials with enhanced light-emitting properties.
6. Used in Gold (III)-Catalyzed Hydroamination:
In a study involving a gold (III)-catalyzed hydroamination of alkynes, 4-Ethynylanisole is used to produce N-vinylindoles, which are valuable intermediates in the synthesis of various organic compounds and pharmaceuticals.
7. Used in Copper-Catalyzed Synthesis:
4-Ethynylanisole is involved in a three-component synthesis of trisubstituted 1,2,4-triazoles, along with an arylboronic acid and sodium azide, in a copper-catalyzed reaction. This process is significant in the development of novel chemical compounds with potential applications in various industries.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 9, p. 230, 1998Synthesis, p. 305, 1978Tetrahedron, 62, p. 6673, 2006 DOI: 10.1016/j.tet.2005.12.077

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 696-62-8 para-iodoanisole 
• 74-86-2 acetylene 
• 107-19-7 propargyl alcohol 
• 268536-10-3 6-anisyl-1,3-dioxine-4-thione 
• 123-11-5 4-methoxy-benzaldehyde 
• 60-29-7 diethyl ether 
• 87992-04-9 4-(1,2-dichloro-vinyl)-anisole 
• 27570-08-7 4-(2-bromo-vinyl)-anisole 
• 136053-40-2 4-Methoxy-2-trimethylsilanyl-1-trimethylsilanylethynyl-benzene 
• 6303-59-9 (Z)-1-bromo-2-(4-methoxyphenyl)ethene 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 88649-20-1 (1R,5S)-3-(4-Methoxy-phenyl)-3-methyl-tricyclo[3.2.1.0^2,4]octane 
• 293757-13-8 2,7-bis[(4-methoxyphenyl)ethynyl]-9H-fluoren-9-one 
• 20979-50-4 4,7-dimethoxyflavone 
• 63675-74-1 2-(4'-methoxyphenyl)-6-methoxybenzothiophene 
• 32291-90-0 (Z)-(4-methoxystyryl)(p-tolyl)sulfane 
• 32291-89-7 (E)-(4-methoxystyryl)(p-tolyl)sulfane 
• 29910-92-7 3-(4-methoxyphenyl)-1H-isochromen-1-one 
• 25914-38-9 2-hydroxy-2-(4-methoxy-phenylethynyl)-1,3-dimethyl-cyclohexanecarboxylic acid ethyl ester 
• 60512-44-9 1-(p-Anisylethynyl)cyclopropanol 
• 169212-86-6 methyl 2-methoxy-6-<(4-methoxyphenyl)ethynyl>benzoate 
• 2739-04-0 N-methyl-N-(4-methylphenyl)formamide 
• 623-08-5 N-methyl-p-toluidine 
• 69374-90-9 1,4-Bis<4-(tetradecyloxy)phenyl>-1,3-butadiyne 

Relevant articles and documents

Preparation and properties of high birefringence phenylacetylene isothiocyanato-based blend liquid crystals

A series of compounds of with high birefringence containing alkoxy–phenylacetylene–isothiocyanato structure were synthesized and characterized. The chemical structures of these compounds were confirmed by FT-IR and 1H-NMR, and transition temperatures and birefringence were measured. One of these compounds with good liquid crystal property and high birefringence was mixed with host liquid crystal to form blend liquid crystal. The effects of the concentration of the compound on phase temperature range, birefringence, resistivity, dielectric anisotropy and photoelectric properties were discussed. The results showed that blend liquid crystal (with 7 wt% compound) exhibited excellent comprehensive performance.

Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

A novel copper-mediated or transition-metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents was described. The outcomes of these reactions were found to be highly dependent on the reaction conditions and

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.