33491-04-2

Basic information

• Product Name: Benzene, 1-(chloroethynyl)-4-methyl-
• CAS NO: 33491-04-2
• Molecular Formula: C9H7Cl
• Molecular Weight: 150.608
• Mol File: 33491-04-2.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(chloroethynyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(chloroethynyl)-4-methyl-(33491-04-2)
• EPA Substance Registry System: Benzene, 1-(chloroethynyl)-4-methyl-(33491-04-2)

Safety Data

• Hazardous Substances Data: 33491-04-2(Hazardous Substances Data)

Upstream product

• 4714-37-8 1-(2,2-dichlorovinyl)-4-methylbenzene 
• 106-38-7 para-bromotoluene 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 1777-53-3 1-(p-tolyl)-2-(triphenylphosphoranylidene)ethanone 
• 98-09-9 benzenesulfonyl chloride 
• 7572-29-4 dichloroethyne 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 104-87-0 4-methyl-benzaldehyde 
• 766-97-2 4-n-methylphenylacetylene 
• 64-19-7 acetic acid 
• 19233-57-9 2-Chloro-1-p-tolyl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 

Downstream Products

• 622-97-9 1-ethenyl-4-methylbenzene 
• 1377939-77-9 (Z)-N-(2-chloro-1-(p-tolyl)vinyl)acetamide 
• 1005500-78-6 N,4-dimethyl-N-(p-tolylethynyl)benzenesulfonamide 
• 70626-00-5 (Z)-2-Chloro-3-phenyl-1-p-tolyl-propenone 

Relevant articles and documents

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Gold-Catalyzed Highly Chemo- and Regioselective C-H Bond Functionalization of Phenols with Haloalkynes

A highly chemo- and stereoselective addition of unprotected phenols to haloalkynes was developed. A ligand and counterion controlled process enabled the highly site-selective and chemoselective C-H bond functionalization of phenol derivatives with haloalkynes in moderate to excellent yield at room temperature. The simple availability of the starting materials in combination with the preferred para-C-H functionalization over a competing O-H insertion makes this an attractive protocol. The stereoselectivity of the products depends on the choice of the catalyst. From a synthetic prospective, this method offers an efficient route towards vinyl chlorides, which are valuable precursors for the synthesis of pharmaceutical drugs.

Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes

The [2+2] cycloaddition is a versatile strategy for the synthesis of strained cyclobutenes of high synthetic value. In this study, two efficient intermolecular [2+2] cycloadditions between two different types of chloroalkynes and unactivated alkene are realized with gold catalysis. Of significance is that the reaction works with challenging monosubstituted unactivated alkenes, which is unprecedented in gold catalysis and scarcely documented in other metal-catalyzed/promoted reactions; moreover, the reaction exhibits excellent regioselectivities, which are much better than those reported in literature. With 1,2-disubstituted unactivated alkenes, the reaction is largely stereospecific. The cyclobutene products can be prepared in nearly gram scale and readily undergo further reactions including various cross-coupling reactions using the C(sp2)-Cl and/or C(sp2)-SPh bond, which in turn substantially broaden the scope of accessible cyclobutenes and enhance the synthetic utility of this bimolecular reaction.