101300-64-5

Basic information

• Product Name: 1,2-bis(trimethylsilyl)-4-methylbenzene
• Synonyms: 1,2-bis(trimethylsilyl)-4-methylbenzene
• CAS NO: 101300-64-5
• Molecular Weight: 236.505
• Mol File: 101300-64-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,2-bis(trimethylsilyl)-4-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis(trimethylsilyl)-4-methylbenzene(101300-64-5)
• EPA Substance Registry System: 1,2-bis(trimethylsilyl)-4-methylbenzene(101300-64-5)

Safety Data

• Hazardous Substances Data: 101300-64-5(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 60956-23-2 3,4-dibromotoluene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 17151-09-6 1,2-bis(trimethylsilyl)benzene 
• 1369371-68-5 4-pinacolatoboryl-1,2-bis(trimethylsilyl)benzene 
• 1369371-66-3 3,5-dibromo-1,2-bis(trimethylsilyl)benzene 
• 1369371-65-2 4-bromo-1,2-bis(trimethylsilyl)benzene 
• 74-88-4 methyl iodide 
• 95-75-0 3,4-Dichlorotoluene 
• 87226-80-0 1,2-bis(trimethylsilyl)-4-methylcyclohexa-1,4-diene 

Downstream Products

• 21991-42-4 6-methyl-1,2,3,4-tetraphenylnaphthalene 

Relevant articles and documents

A new and efficient hypervalent iodine-benzyne precursor, (phenyl)[o- (trimethylsilyl)phenyl]iodonium triflate: Generation, trapping reaction, and nature of benzyne

A new and efficient hypervalent iodine-benzyne precursor, (phenyl)[2- (trimethylsilyl)phenyl]-iodonium triflate (10), is reported. The hypervalent iodine-benzyne precursor 10 is readily prepared by reaction of 1,2- bis(trimethylsilyl)benzene with a PhI(OAc)2/TfOH reagent system. Treatment of 10 with Bu4NF in CH2Cl2 at room temperature gives high yields of the benzyne adducts in the presence of a trapping agent such as furan, 2- methylfuran, anthracene, tetraphenylcyclopentadienone, or 1,3- diphenylisobenzofuran. Especially, the result of the reaction in the presence of furan indicates a quantitative generation of benzyne and its efficient capture by the furan. Similarly, methylbenzynes (22 and 27) are efficiently generated from the corresponding methyl-substituted (trimethylsilyl)phenyliodonium triflates (12 and 13). The preparation of the hypervalent iodine-benzyne precursors, the generation of benzynes, the trapping reactions, and the nature are described in detail together with the advantages of the present reagents over the previously reported benzyne precursors.

1,2-bis (methylsilyl triarylboron) or its method of manufacturing cd87 compd. hydroxybenzenesulfonic

PROBLEM TO BE SOLVED: To provide a new method for producing 1,2-bis(trimethylsilyl)benzene or its analogous compound at a low cost in high yield under a mild reaction condition by using a safe solvent.SOLUTION: There is provided a method for producing 1,2

Synthesis of bromo-, boryl-, and stannyl-functionalized 1,2-bis(trimethylsilyl)benzenes via Diels-Alder or C-H activation reactions

1,2-Bis(trimethylsilyl)benzenes are key starting materials for the synthesis of benzyne precursors, Lewis acid catalysts, and certain luminophores. We have developed efficient, high-yield routes to functionalized 4-R-1,2-bis(trimethylsilyl)benzenes, starting from either 1,2- bis(trimethylsilyl)acetylene/5-bromopyran-2-one (2) or 1,2-bis(trimethylsilyl) benzene (1)/bis(pinacolato)diborane. In the first reaction, 5 (R = Br) is obtained through a cobalt-catalyzed Diels-Alder cycloaddition. The second reaction proceeds via iridium-mediated C-H activation and provides 8 (R = Bpin). Besides its use as a Suzuki reagent, compound 8 can be converted into 5 with CuBr2 in i-PrOH/MeOH/H2O. Lithium-bromine exchange on 5, followed by the addition of Me3SnCl, gives 10 (R = SnMe3), which we have applied for Stille coupling reactions. A Pd-catalyzed C-C coupling reaction between 5 and 8 leads to the corresponding tetrasilylbiphenyl derivative. The bromo derivative 5 cleanly undergoes Suzuki reactions with electron-rich as well as electron-poor phenylboronic acids.