2765-16-4

Basic information

• Product Name: Benzene, 1,1'-(1,2-ethynediyl)bis[3-methyl-
• CAS NO: 2765-16-4
• Molecular Formula: C16H14
• Molecular Weight: 206.287
• Mol File: 2765-16-4.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(1,2-ethynediyl)bis[3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(1,2-ethynediyl)bis[3-methyl-(2765-16-4)
• EPA Substance Registry System: Benzene, 1,1'-(1,2-ethynediyl)bis[3-methyl-(2765-16-4)

Safety Data

• Hazardous Substances Data: 2765-16-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Manufacturing:
Benzene, 1,1'-(1,2-ethynediyl)bis[3-methylis used as a key intermediate in the synthesis of various chemical products. Its unique structure allows it to participate in a wide range of chemical reactions, making it a valuable component in the production of different compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzene, 1,1'-(1,2-ethynediyl)bis[3-methylis used as a building block for the development of new drugs. Its versatile chemical properties enable it to be incorporated into the molecular structures of potential therapeutic agents, contributing to the discovery of novel medications.
Used in Material Science:
Benzene, 1,1'-(1,2-ethynediyl)bis[3-methylis also utilized in material science for the creation of advanced materials with specific properties. Its incorporation into polymers and other materials can lead to the development of new products with improved characteristics, such as enhanced stability or increased reactivity.
Used in Research and Development:
In the field of research and development, Benzene, 1,1'-(1,2-ethynediyl)bis[3-methylserves as a model compound for studying the properties and behavior of aromatic hydrocarbons. Its use in academic and industrial research helps to advance our understanding of chemical reactions and the development of new synthetic strategies.

Upstream product

• 74844-05-6 C₁₆H₁₅Br 
• 18826-62-5 1-methyl-3-(prop-1-yn-1-yl)benzene 
• 75-20-7 calcium carbide 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 5963-39-3 hex-3-yne-1,6-dioic acid 
• 591-17-3 meta-bromotoluene 
• 625-95-6 3-Iodotoluene 
• 471-25-0 Propiolic acid 
• 17933-03-8 m-tolylboronic acid 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 40230-90-8 (2-(3-methylphenyl)ethynyl)trimethylsilane 
• 108-41-8 1-chloro-3-methylbenzene 
• 624-31-7 4-tolyl iodide 
• 766-82-5 1-ethynyl-3-methyl-benzene 

Downstream Products

• 4463-26-7 3,3'-dimethylbenzil 
• 132733-33-6 3,4-Di(m-tolyl)-1,2,5-thiadiazole 
• 55860-36-1 1-acetyl-4-carboxy methyl benzene 
• 1383663-47-5 (Z)-1-(1,2-di-m-tolylvinyl)-5-methoxy-1H-indole 
• 1427041-77-7 3-(4-chlorophenyl)-Z-4-ethylidene-2-methyl-3,4-dihydroisoquinolinone 
• 1427041-78-8 C₁₈H₁₆ClNO 
• 1469444-90-3 1,1,2-tri-m-tolylethene 
• 1059620-01-7 (Z)-1-methyl-3-(2-phenyl-2-m-tolylvinyl)benzene 

Relevant articles and documents

Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives

Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.

Nickel-Catalyzed One-Pot Carbonylative Synthesis of 2-Mono- And 2,3-Disubstituted Thiochromenones from 2-Bromobenzenesulfonyl Chlorides and Alkynes

A nickel-catalyzed one-pot carbonylation reaction of 2-bromobenzenesulfonyl chlorides with alkynes for the synthesis of thiochromenones has been established. Both terminal and internal alkynes were suitable substrates in this carbonylative transformation, and a broad range of 2-mono- and 2,3-disubstituted thiochromenone products were obtained in moderate to good yields with quite high functional group compatibility. Notably, this procedure presents the first example of nickel-catalyzed carbonylative synthesis of thiochromenones with 2-bromobenzenesulfonyl chlorides as a promising sulfur precursor.

Palladium(II)-Catalyzed Oxidative Decarboxylative [2 + 2 + 1] Annulation of Cinnamic Acids with Alkynes: Access to Polysubstituted Pentafulvenes

An unprecedented palladium(II)-catalyzed oxidative decarboxylative [2 + 2 + 1] annulation of cinnamic acids with alkynes has been developed for the synthesis of polysubstituted pentafulvenes. Ag2CO3 and DMSO are essential for the reaction. This protocol features readily available starting materials, a wide substrate scope, and moderate to excellent yields. Moreover, various significant frameworks can be easily obtained from the late-stage transformations of pentafulvenes via oxidation, reduction, and Scholl-type reaction.

Ruthenium(ii)-catalyzed intermolecular annulation of alkenyl sulfonamides with alkynes: Access to bicyclic sultams

A ruthenium-catalyzed allylic C(sp3)-H activation strategy has been employed to develop an intermolecular coupling of alkenyl sulfonamides with alkynes. This protocol features the diastereoselective construction of [3.3.0] and [4.3.0] bicyclic sultams in one step.

The ruthenium(ii)-catalyzed C-H olefination of indoles with alkynes: The facile construction of tetrasubstituted alkenes under aqueous conditions

An environmentally-friendly and facile protocol for the construction of tetrasubstituted alkenes has been established with Ru(ii)-catalyzed C-H bond functionalizations under mild conditions. The method features the usage of readily available substrates, without external oxidants and additives, 100% atom economy, and excellent regioselectivity, thus enhancing the practicability of this protocol. Moreover, this transformation proceeded smoothly under aqueous conditions and could be extended to the gram scale. N-Methoxyamide, as a directing group (DG), played a vital role in the transformation.

A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: A significant substituent effect

We described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and experimental data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.