276856-72-5

Basic information

• Product Name: 3,5-dimethyl-1-(trimethylsilylethynyl)benzene
• Synonyms: 3,5-dimethyl-1-(trimethylsilylethynyl)benzene
• CAS NO: 276856-72-5
• Molecular Weight: 202.371
• Mol File: 276856-72-5.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 3,5-dimethyl-1-(trimethylsilylethynyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dimethyl-1-(trimethylsilylethynyl)benzene(276856-72-5)
• EPA Substance Registry System: 3,5-dimethyl-1-(trimethylsilylethynyl)benzene(276856-72-5)

Safety Data

• Hazardous Substances Data: 276856-72-5(Hazardous Substances Data)

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 556-96-7 5-bromo-1,3-xylene 
• 22445-41-6 3,5-dimethylphenyl iodide 

Downstream Products

• 1595282-11-3 (Z)-(2-(3,5-dimethylphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)trimethylsilane 
• 1613059-74-7 1-(3,5-dimethylphenyl)-2-(phenylsulfonyl)ethanone 
• 1612866-59-7 2-(3,5-dimethylphenyl)phenanthren-4-ol 
• 1612866-60-0 C₄₄H₃₄O₂ 
• 107146-56-5 1,2-bis(3,5-dimethylphenyl)acetylene 

Relevant articles and documents

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles

For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.

Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions

A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (TMSA) as a convenient acetylene surrogate was also shown to be feasible under Pd/Cu catalysis.