177166-37-9

Basic information

• Product Name: 2,5-Diisopropylphenyl-tris(trimethylsilyl)methanol
• Synonyms: 2,5-Diisopropylphenyl-tris(trimethylsilyl)methanol
• CAS NO: 177166-37-9
• Molecular Weight: 438.949
• Mol File: 177166-37-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,5-Diisopropylphenyl-tris(trimethylsilyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diisopropylphenyl-tris(trimethylsilyl)methanol(177166-37-9)
• EPA Substance Registry System: 2,5-Diisopropylphenyl-tris(trimethylsilyl)methanol(177166-37-9)

Safety Data

• Hazardous Substances Data: 177166-37-9(Hazardous Substances Data)

Upstream product

• 4110-02-5 tris(trimethylsilyl)silyllithium 
• 74598-75-7 2,5-di-isopropylbenzaldehyde 

Relevant articles and documents

Synthesis and dimerization behavior of 1,1-bis(trimethylsilyl)-2-(2,5-diisopropylphenyl)silene

Tris(trimethylsilyl)silylmagnesium bromide, (Me3Si)3SiMgBr, reacts with 2,5-diisopropyl-benzaldehyde to give 2,5-diisopropylphenyl-tris(trimethylsilyl)silylmethanol (1). With sodium hydride in THF compound 1 undergoes a rearrangement through 1,3-Si,O-trimethylsilyl migration affording bis(trimethylsilyl)silyl-(2.5-diisopropylphenyl)-trimethylsiloxy-methane (4). The deprotonation of 1 with organolithium reagents in ether leads to the elimination of lithium trimethylsilanolate according to a modified Peterson mechanism resulting in the formation of the transient silene (Me3Si)2Si=CH(2.5-iPr2C6H 3) (2). Treatment of 1 with an excess of phenyllithium in diethylether at low temperature gives 1,1,1,3,3,3-hexamethyl-2-phenyl-2-(2,5-diisopropylbenzyl)-trisilane (3), formed in a nucleophilic addition of the excess PhLi to the silene intermediate and in the hydrolytic workup. Stochiometric quantities of MeLi in diethylether at -78 °C convert compound 1 into a head-to-head dimer of the silene 1,2,3,8a-tetrahydro-5,8-diisopropyl-1-(2,5-diisopropylphenyl)-2,2,3,3-tetrakis- (trimethylsilyl)-2,3-disilanaphthalene (5). Compound 5, presumably the kinetically preferred product of the cyclodimerization of 2, gradually transforms into the thermodynamically stable 3,4-bis(2,5-diisopropylphenyl)-1,1,2,2-tetrakis(trimethyl-silyl)-1,2- disilacyclobutane (6). The E/Z-isomers of 6 have been characterized by X-ray crystal structural analyses.