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

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

Used in Pharmaceutical Synthesis:
2-Ethynylbenzaldehyde is used as a key intermediate in the synthesis of iodoisoquinoline-fused benzimidazoles. These compounds are obtained through a tandem iodocyclization process involving 2-ethynylbenzaldehyde, o-benzenediamine, and iodine in the presence of copper(I) iodide. This application is significant in the development of pharmaceutical compounds with potential therapeutic properties.
Used in Organic Synthesis:
2-Ethynylbenzaldehyde is also utilized in the synthesis of N-[(7,7a-dihydroisoquinolino[2,1-a]perimidin-13-yl)methyl]-N-isopropylpropan-2-amine, which is achieved through a multi-step process. 2-ETHYNYLBENZALDEHYDE may have applications in various fields, including pharmaceuticals and materials science.
Used in the Synthesis of Substituted 2-Alkynylbenzaldehydes:
2-Ethynylbenzaldehyde is employed in the preparation of various substituted 2-alkynylbenzaldehydes through Sonogashira coupling. This method allows for the formation of carbon-carbon bonds between the ethynyl group of 2-ethynylbenzaldehyde and different brominated aromatic rings. The resulting substituted 2-alkynylbenzaldehydes include:
2-[(2-bromophenyl)ethynyl]benzaldehyde
2-[(2-bromo-5-fluorophenyl)ethynyl]benzaldehyde
2-[(2-bromo-5-methylphenyl)ethynyl]benzaldehyde
2-(phenylethynyl)benzaldehyde
2-[(4-methylphenyl)ethynyl]benzaldehyde
These substituted 2-alkynylbenzaldehydes can be used as building blocks in the synthesis of more complex organic molecules, with potential applications in various industries such as pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 139334-70-6 C₁₀H₉NO 
• 68-12-2 N,N-dimethyl-formamide 
• 536-74-3 phenylacetylene 
• 88180-40-9 methylenebenzocyclobutenone 
• 88180-41-0 3-((benzoyloxy)methyl)benzofuran 
• 200957-26-2 (7-oxa-1-benzonorbornenyl)methyl benzoate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 26260-02-6 2-iodobenzaldehyde 
• 10602-08-1 2-ethynylbenzyl alcohol 
• 141791-38-0 1-ethenyl-2-[2-(trimethylsilyl)ethynyl]benzene 
• 74-86-2 acetylene 
• 38846-62-7 o-<1,2-Dibromethyl>-benzaldehyd 

Downstream Products

• 72563-62-3 1,7-bis-(o-ethynylphenyl)-4-methylhepta-1,4,6-trien-3-one 
• 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 
• 55077-88-8 1,5-bis(2-ethynylphenyl)penta-1,4-dien-3-one 
• 64432-74-2 (E)-4-(2-ethynylphenyl)but-3-en-2-one 
• 80684-57-7 2,2-dimethyl-6-(o-ethynylphenyl)-5-hexen-4-one 
• 74794-98-2 2-(o-ethynylphenyl)vinyl 4-(o-ethynylphenyl)-1,3-butadienyl sulfide 
• 139334-70-6 C₁₀H₉NO 
• 74794-95-9 bis<2-(o-ethynylphenyl)vinyl> sulfide 
• 74794-94-8 bis<2-(o-ethynylphenyl)vinyl> sulfide 
• 74794-93-7 bis<2-(o-ethynylphenyl)vinyl> sulfide 

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.

A structure-activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

Inhibition of the enzymatic activity of histone deacetylase (HDAC) is a promising therapeutic strategy for cancer treatment and several distinct small molecule histone deacetylase inhibitors (HDACi) have been reported. We have previously identified a new class of non-peptide macrocyclic HDACi derived from 14- and 15-membered macrolide skeletons. In these HDACi, the macrocyclic ring is linked to the zinc chelating hydroxamate moiety through a para-substituted aryl-triazole cap group. To further delineate the depth of the SAR of this class of HDACi, we have synthesized series of analogous compounds and investigated the influence of various substitution patterns on their HDAC inhibitory, anti-proliferative and anti-inflammatory activities. We identified compounds 25b and 38f with robust anti-proliferative activities and compound 26f (IC50 47.2 nM) with superior anti-inflammatory (IC50 88 nM) activity relative to SAHA.

Synthesis of Fused Pyrimido[1,6- a ]indolones via Rhodium(III)-Catalyzed Cascade Annulations

A novel method for the synthesis of fused pyrimido[1,6- a ]-indolone derivatives by annulation of 2-alkynylaryl aldehydes/2-alkynyl arylidene ketones with N -(pivaloyloxy)-1 H -indole-1-carboxamide catalyzed by rhodium has been accomplished. The reaction proceeds through C-H activation based annulation with alkyne moiety followed by addition of nitrogen on to aldehyde/activated alkene to give the products in moderate to good yields. Highly fluorescent dipyrrinone analogues could be synthesized from the derived products.

One-pot Synthesis of Isoquinoline-Fused Isoquinolines via Intramolecular Hydroamination/Aza-Claisen Type Rearrangement Cascade

A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from α-amino acid esters and 2-alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular hydroamination followed by aza-Claisen type rearrangement. (Figure presented.).

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.).

Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O-Heterocycle Confined 1,3-Dienes

The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C-N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method possesses broad substrate generality as well as functional group compatibility and efficiently affords a wide range of desired products with 5-, 6-, and 8-membered O-containing heterocycles with various functional groups.

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.

Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property

A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.

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.).

Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides by NaI/PPh3Catalysis

A practical and eco-friendly strategy for the radical-mediated decarboxylative [3 + 2] and [4 + 2] annulation of enynals and γ,σ-unsaturated N-(acyloxy)phthalimides through the photoactivation of an electron donor-acceptor (EDA) complex has been developed. A wide range of primary, secondary, and tertiary alkyl N-hydroxyphthalimide (NHP) esters can be used as suitable substrates for the synthesis of fused ketones without any transition-metal catalysts or oxidants. This protocol features a broad substrate scope, excellent selectivity, and clean reaction conditions.