39165-03-2

Basic information

• Product Name: 2-ETHYNYL-BENZO[B]FURAN
• Synonyms: 2-ETHYNYL-BENZO[B]FURAN;2-Ethynylbenzofuran
• CAS NO: 39165-03-2
• Molecular Formula: C₁₀H₆O
• Molecular Weight: 142.15404
• Mol File: 39165-03-2.mol

Chemical Properties

• Boiling Point: 221.091°C at 760 mmHg
• Flash Point: 89.04°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 0.162mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 2-ETHYNYL-BENZO[B]FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYNYL-BENZO[B]FURAN(39165-03-2)
• EPA Substance Registry System: 2-ETHYNYL-BENZO[B]FURAN(39165-03-2)

Safety Data

• Hazardous Substances Data: 39165-03-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H6O/c1-2-9-7-8-5-3-4-6-10(8)11-9/h1,3-7H

Upstream product

• 113639-24-0 1-Benzofuran-2-yl-2-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-ethanone 
• 69626-75-1 2-iodobenzofuran 
• 4301-14-8 acetylenemagnesium bromide 
• 558-13-4 carbon tetrabromide 
• 4265-16-1 2-formylbenzo[b]furan 
• 474267-30-6 benzofuran-2-ylethynyltrimethylsilane 
• 1066-54-2 trimethylsilylacetylene 
• 54008-77-4 2-bromo-1-benzofuran 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 860638-24-0 2-(2,2-dibromovinyl)benzofuran 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 41717-28-6 2-benzofuroyl chloride 
• 271-89-6 1-benzofurane 
• 1004960-33-1 2-(4-trimethylsilyl-1,3-butadiyn-1-yl)-(tert-butyldimethylsilyl)oxybenzene 

Downstream Products

• 1207638-40-1 4-(benzofuran-2-yl)-1-(4-iodobenzyl)-1H-1,2,3-triazole 
• 1207638-45-6 4-(benzofuran-2-yl)-1-(3-iodobenzyl)-1H-1,2,3-triazole 

Relevant articles and documents

Cyclohepta[ b]indole Synthesis through [5 + 2] Cycloaddition: Bifunctional Indium(III)-Catalyzed Stereoselective Construction of 7-Membered Ring Fused Indoles

A new approach for the synthesis of highly functionalized tetrahydrocyclohepta[b]indoles through [5 + 2] cycloaddition was developed. Two carbon-carbon bonds were formed by the simple addition of an indium catalyst, which acted as both a δ-Lewis acid and σ-Lewis acid to activate the alkyne and unsaturated ester, respectively. The reaction could be applied to various substrates and proceeded regio- and diastereoselectively in all cases.

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.

DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes

Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).

Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives

A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.

Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes

A copper-catalyzed decarboxylative alkylation of terminal alkynes under mild reaction conditions has been reported. Various alkyl diacyl peroxides were applied as the alkyl source for the formation of C(sp3)?C(sp) bond. A range of terminal alkynes including aryl alkynes and alkyl alkynes delivered the alkylated internal alkynes with good to high performances. Mechanism studies suggested that this reaction involves a free radical pathway. (Figure presented.).

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity

The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.

MGLUR REGULATORS

Provided herein are compounds of the formula I: (I), as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment or prevention of mGluR5 mediated disorders, such as acute and/or chronic neurological disorders, cognitive disorders and memory deficits, as well as acute and chronic pain.

A straightforward synthesis of indole and benzofuran derivatives

A new methodology for the synthesis of indole and benzofuran derivatives has been devised. The starting materials, ortho-substituted aryl diynes, have been easily converted into new unsaturated bis-indolyl and bis-benzofuran derivatives and into 2-ethynylindole and 2-ethynylbenzofuran. Both these products have been further elaborated into more complex unsaturated indole-benzofuran and bis-benzofuran derivatives.

TRICYCLIC PYRAZOLE KINASE INHIBITORS

Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.