38846-64-9

Basic information

• Product Name: 2-ETHYNYLBENZALDEHYDE
• Synonyms: 2-Ethynylbenzaldehyde97%;2-ETHYNYLBENZALDEHYDE;2-ETHYLNYLBENZALDEHYDE, 97%;Benzaldehyde, 2-ethynyl- (9CI);2-Ethynylbenzaldehyde 97%;2-Formylphenylacetylene
• CAS NO: 38846-64-9
• Molecular Formula: C₉H₆O
• Molecular Weight: 130.14
• Product Categories: Aldehydes;C9;Carbonyl Compounds
• Mol File: 38846-64-9.mol
• Article Data: 62

Chemical Properties

• Melting Point: 64-67 °C(lit.)
• Boiling Point: 230.3 °C at 760 mmHg
• Flash Point: 90.8 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0.0662mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-ETHYNYLBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYNYLBENZALDEHYDE(38846-64-9)
• EPA Substance Registry System: 2-ETHYNYLBENZALDEHYDE(38846-64-9)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 38846-64-9(Hazardous Substances Data)

Usage

Uses

2-Ethynylbenzaldehyde may be used in the synthesis of the following:iodoisoquinoline-fused benzimidazoles obtained via tandem iodocyclization of 2-ethynylbenzaldehyde with o-benzenediamine and iodine in the presence of copper(I)iodideN-[(7,7a-dihydroisoquinolino[2,1-a]perimidin-13-yl)methyl]-N-isopropylpropan-2-amine obtained via a multi-step processIt may also be used in the synthesis of the following substituted 2-alkynylbenzaldehydes by Sonogashira coupling:2-[(2-bromophenyl)ethynyl]benzaldehyde2-[(2-bromo-5-fluorophenyl)ethynyl]benzaldehyde2-[(2-bromo-5-methylphenyl)ethynyl]benzaldehyde2-(phenylethynyl)benzaldehyde2-[(4-methylphenyl)ethynyl]benzaldehyde

InChI:InChI=1/C9H6O/c1-2-8-5-3-4-6-9(8)7-10/h1,3-7H

Upstream product

• 139334-70-6 C₁₀H₉NO 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 141791-38-0 1-ethenyl-2-[2-(trimethylsilyl)ethynyl]benzene 
• 10602-08-1 2-ethynylbenzyl alcohol 
• 26260-02-6 2-iodobenzaldehyde 
• 74-86-2 acetylene 
• 396717-20-7 2-[(triisopropylsilanyl)-ethynyl]-benzaldehyde 
• 28272-96-0 2-vinylbenzaldehyde 
• 200957-26-2 (7-oxa-1-benzonorbornenyl)methyl benzoate 
• 88180-41-0 3-((benzoyloxy)methyl)benzofuran 
• 88180-40-9 methylenebenzocyclobutenone 
• 68-12-2 N,N-dimethyl-formamide 
• 536-74-3 phenylacetylene 

Downstream Products

• 63697-97-2 1,2,4,5-tetra<(Z)-2(2-ethynylphenyl)ethenyl>benzene 
• 62051-72-3 trans-trans 1,2-bis<2-(2-ethynylphenyl)ethenyl>benzene 
• 72563-60-1 1-(o-ethynylphenyl)-4,9-dimethylundeca-1,4,6,8-tetraen-10-yn-3-one 
• 68520-93-4 N,N'-Bis-[1-(2-ethynyl-phenyl)-meth-(E)-ylidene]-hydrazine 
• 80371-97-7 (E)-3-(2-ethynylphenyl)-1-phenylprop-2-en-1-one 
• 75586-29-7 2-ethynylbenzaldehyde benzoylhydrazone 
• 80352-37-0 1-(m-Bromophenyl)-3-(o-ethynylphenyl)-2-propen-1-one 
• 80352-33-6 3-(o-Ethynylphenyl)-1-(p-methylphenyl)-2-propen-1-one 
• 343232-24-6 2-ethynylbenzaldehyde tosylhydrazone 
• 171070-82-9 1-(2-ethynylphenyl)-hept-2-yn-1-ol 
• 300345-24-8 C₂₄H₁₄O₂ 

Relevant articles and documents

Selectivity-switchable construction of benzo-fused polycyclic compounds through a gold-catalyzed reaction of enyne-lactone

A gold-catalyzed selectivity-switchable reaction of enyne-lactone is reported. Different products, including naphthalenes and benzo-fused polycyclic compounds, can be selectively obtained from the same starting material. The choice of the gold complex is the key for the chemoselectivity of this system.

Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds

Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).

Au(I)/(R)-BINOL-Ti(IV) concerted catalyzed asymmetric cascade cycloaddition reaction of arylalkynols

An efficient catalytic asymmetric cascade cycloaddition reaction of arylalkynols with dioxopyrrolidines was developed. This reaction was achieved using Au(I) and (R)-BINOL-Ti(IV) bimetallic catalysts and exclusively delivered a series of chiral oxo-bridged bicyclic benzooxacine compounds in up to 86% yield with 96% ee as well as >33:1 dr. Meanwhile, three new σ bonds and three new stereogenic centers were formed in a one-pot process.

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).