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38846-64-9

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38846-64-9 Usage

Description

2-Ethynylbenzaldehyde is an organic compound characterized by an ethynyl group attached to a benzene ring and a formyl group. It serves as a versatile intermediate in organic synthesis, particularly in the preparation of various heterocyclic compounds and substituted 2-alkynylbenzaldehydes.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 38846-64-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,8,4 and 6 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 38846-64:
(7*3)+(6*8)+(5*8)+(4*4)+(3*6)+(2*6)+(1*4)=159
159 % 10 = 9
So 38846-64-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H6O/c1-2-8-5-3-4-6-9(8)7-10/h1,3-7H

38846-64-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-ETHYNYLBENZALDEHYDE

1.2 Other means of identification

Product number -
Other names ortho-ethynylbenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:38846-64-9 SDS

38846-64-9Relevant articles and documents

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

Luo, Kui,Zhang, Ling,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa

, p. 1893 - 1896 (2018)

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.

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

Raji Reddy, Chada,Bodasu, Srinivas,Mallesh, Kathe,Prapurna, Y. Lakshmi

, p. 1127 - 1136 (2020/10/29)

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.

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

Li, Quanzhe,Liu, Ruixing,Wei, Yin,Shi, Min

supporting information, p. 2664 - 2669 (2021/04/05)

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

Wang, Hongkai,Zeng, Tianlong,Chang, Weixing,Liu, Lingyan,Li, Jing

supporting information, p. 3573 - 3577 (2021/05/31)

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.

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