767-91-9

Basic information

• Product Name: 1-ETHYNYL-2-METHOXYBENZENE
• Synonyms: SALOR-INT L308617-1EA;1-ETHYNYL-2-METHOXYBENZENE;2'-METHOXYPHENYL ACETYLENE;2-ETHYNYLANISOLE;Benzene, 1-ethynyl-2-methoxy- (9CI);2-Ethynylanisole,1-Ethynyl-2-methoxybenzene;Benzene, 1-ethynyl-2-Methoxy-;1-Etynyl-2-Methoxy-Benzene
• CAS NO: 767-91-9
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.16
• Mol File: 767-91-9.mol
• Article Data: 56

Chemical Properties

• Boiling Point: 197 °C(lit.)
• Flash Point: 91 °C
• Appearance: /
• Density: 1.022 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.368mmHg at 25°C
• Refractive Index: n20/D 1.5720(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-ETHYNYL-2-METHOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYNYL-2-METHOXYBENZENE(767-91-9)
• EPA Substance Registry System: 1-ETHYNYL-2-METHOXYBENZENE(767-91-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 767-91-9(Hazardous Substances Data)

Usage

Description

1-Ethynyl-2-methoxybenzene, also known as 2-ethynylanisole, is an acetylene derivative with the molecular formula C9H8O. It is an organic compound characterized by the presence of a triple bond (ethynyl group) and a methoxy group attached to a benzene ring. 1-ETHYNYL-2-METHOXYBENZENE has been synthesized through a reaction involving 2-iodoanisole and trimethylsilylacetylene, followed by the deprotection of the trimethylsilyl group.

Uses

1. Used in Chemical Synthesis:
1-Ethynyl-2-methoxybenzene is used as a key intermediate in the synthesis of various organic compounds, including 1,4-bis(2-methoxyphenyl)-2-methylbenzene. Its unique structure with the ethynyl and methoxy groups makes it a valuable building block for creating complex organic molecules with diverse applications.
2. Used in Pharmaceutical Industry:
1-Ethynyl-2-methoxybenzene may be utilized in the development of new pharmaceutical compounds due to its structural features. The ethynyl group can be further functionalized, and the methoxy group can impart specific properties to the final product, making it a potential candidate for drug discovery and development.
3. Used in Material Science:
In the field of material science, 1-ethynyl-2-methoxybenzene can be employed in the design and synthesis of novel materials with specific properties. Its structural characteristics may contribute to the development of advanced materials with applications in electronics, optics, or as components in various industrial processes.
4. Used in Research and Development:
1-Ethynyl-2-methoxybenzene serves as a valuable compound for research purposes, particularly in the study of acetylene chemistry and the exploration of new synthetic routes. It can be used to investigate the reactivity of the ethynyl and methoxy groups and their influence on the properties of the resulting compounds.

Synthesis Reference(s)

Synthesis, p. 458, 1975 DOI: 10.1055/s-1975-23805

InChI:InChI=1/C9H8O/c1-3-8-6-4-5-7-9(8)10-2/h1,4-7H,2H3

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 40904-92-5 4-(2'-methoxyphenyl)-2-methyl-3-butyn-2-ol 
• 529-28-2 4-iodoanisol 
• 4301-14-8 acetylenemagnesium bromide 
• 105273-33-4 1-chloro-2-(trimethylsilylethynyl)benzene 
• 615-41-8 2-iodochlorobenzene 
• 558-13-4 carbon tetrabromide 
• 135-02-4 ortho-anisaldehyde 
• 74-86-2 acetylene 
• 1066-54-2 trimethylsilylacetylene 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 471-25-0 Propiolic acid 
• 578-57-4 2-bromoanisole 
• 156423-17-5 (Z)-1-(2-iodovinyl)-2-methoxybenzene 

Downstream Products

• 41398-67-8 2-phenylethynylanisole 
• 97871-86-8 (Z)-2-(2-methoxybenzylidene)benzofuran-3(2H)-one 
• 19725-47-4 2'-methoxyflavone 
• 138330-49-1 1-[(5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-3-(2-methoxy-phenyl)-propynone 
• 7706-86-7 4-(2-methoxyphenyl)-furan-2(5H)-one 
• 143392-21-6 3-(2-methoxyphenyl)furan-2(5H)-one 
• 25914-40-3 2-Hydroxy-2-(2-methoxy-phenylethynyl)-1,3-dimethyl-cyclohexanecarboxylic acid ethyl ester 
• 328086-29-9 3-(2-methoxyphenyl)-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-ol 
• 40756-71-6 2-(2-methoxyphenyl)-1H-indole 
• 199165-20-3 1-bromo-2-(2-methoxyphenyl)acetylene 
• 408353-30-0 2-[(2-methoxyphenyl)ethynyl]aniline 
• 128971-11-9 1-[4-(2-Methoxy-phenyl)-buta-1,3-diynyl]-3,5-bis-trifluoromethyl-benzene 
• 128971-03-9 2-[4-(2-Methoxy-phenyl)-buta-1,3-diynyl]-1,4-bis-trifluoromethyl-benzene 
• 1068657-26-0 ethyl 5-(2-methoxylphenyl)-4-pentynoate 

Relevant articles and documents

Iodocyclisation of Electronically Resistant Alkynes: Synthesis of 2-Carboxy (and sulfoxy)-3-iodobenzo[ b ]thiophenes

The iodocyclisation of alkynes bearing tethered nucleophiles is a highly effective method for the construction and diversification of heterocycles. A key limitation to this methodology is the 5-endo-dig iodocyclisation of alkynes that have an unfavourable electronic bias for electrophilic cyclisation. These tend to direct electrophilic attack of the iodonium atom to the wrong carbon for cyclisation, thus favouring competing addition reactions. Using our previously determined reaction conditions for the 5-endo-dig iodocyclisations of electronically resistant alkynes, we have achieved efficient synthetic access to 2-carboxy (and sulfoxy)-3-iodobenzo[b]thiophenes. The corresponding benzo[b]furans and indoles were not accessible under these conditions. This difference may arise due to the availability of a radical mechanism in the case of iodobenzo[b]thiophenes. The 2-carboxy functionality of the iodocyclised products can be further employed in iterative alkyne-coupling iodocyclisation reactions, where the carboxy group or an imine (Schiff base) partakes in a second iodocyclisation to generate a lactone or pyridine ring.

Divergent Carbocatalytic Routes in Oxidative Coupling of Benzofused Heteroaryl Dimers: A Mechanistic Update

Mildly thermal air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’-dimers, e.g., 2-(benzofuran-2-yl)-1H-indole, to chiral 3,3’-coupled cyclooctatetraenes or carbazole-type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl-type arenium cation mechanisms lead to different products with 2-(benzofuran-2-yl)-1H-indole, being in accord with experimental product distributions.

B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds

An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developedviaa B(C6F5)3-catalyzed cycloaddition reaction ofo-(1-alkynyl)(thio)anisoles oro-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.