70737-20-1

Basic information

• Product Name: Silane, (2-bromoethenyl)trimethyl-, (Z)-
• CAS NO: 70737-20-1
• Molecular Formula: C5H11BrSi
• Molecular Weight: 179.132
• Mol File: 70737-20-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Silane, (2-bromoethenyl)trimethyl-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (2-bromoethenyl)trimethyl-, (Z)-(70737-20-1)
• EPA Substance Registry System: Silane, (2-bromoethenyl)trimethyl-, (Z)-(70737-20-1)

Safety Data

• Hazardous Substances Data: 70737-20-1(Hazardous Substances Data)

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 4298-52-6 2-ethynyl-thiophene 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 931-49-7 1-ethenylcyclohexene 
• 628-71-7 1-Heptyne 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 536-74-3 phenylacetylene 
• 1191-12-4 1-hexynyltrimethylstannane 
• 764-58-9 (E)-hept-3-ene-1-yne 
• 917-92-0 3,3-Dimethylbut-1-yne 

Downstream Products

• 126231-50-3 (E)-1-trimethylsilyl-4-(2-thienyl)-1-buten-3-yne 
• 126231-52-5 (E)-1-trimethylsilyl-4-(1-cyclohexenyl)-1-buten-3-yne 
• 22430-48-4 (1E,3E)-1-trimethylsilyl-5,5-dimethyl-1,3-hexadiene 
• 70960-90-6 trimethyl-nona-1,3t-dien-t-yl-silane 
• 120501-74-8 (E)-1-trimethylsilyl-1-nonen-3-yne 
• 126262-21-3 (1E,5E)-1-trimethylsilyl-1,5-nonadien-3-yne 
• 126231-51-4 (E)-1-trimethylsilyl-1-octen-3-yne 
• 84751-16-6 (E)-1,4-bis(trimethylsilyl)but-3-en-1-yne 
• 92509-53-0 (E)-trimethyl(4-phenylbut-1-en-3-yn-1-yl)silane 
• 133490-32-1 (E)-5-(trimethylsilyl)pent-4-en-2-yn-1-ol 
• 153169-38-1 dimethyl E-2-(trimethylsilyl)vinyl phosphonate 
• 126231-53-6 (E)-6-trimethylsilyl-2-methyl-5-hexen-3-yn-2-ol 

Relevant articles and documents

The synthesis and chemistry of 1,3-bridged polycyclic cyclopropenes: 8-Oxatricyclo[3.2.1.02,4]octa-2,6-dienes

Three 1,3-bridged polycyclic cyclopropenes, exo-8-oxatricyclo[3.2.1.0 2,4]octa-2,6-diene (10), endo-8-oxatricyclo[3.2.1.0 2,4]octa-2,6-diene (11), and exo-6,7-benzo-1,5-diphenyl-8- oxatricyclo[3.2.1.02,4]octa-2,6-diene (12), have been synthesized by elimination of 2-chloro-3-trimethylsilyl-8-oxatricyclo[3.2.1.0 2,4]-oct-6-enes, 17,18 and 30, which were generated from 1-chloro-3-trimethylsilylcyclopropene with furan and diphenylisobenzofuran. We have demonstrated a facile route to synthesize the highly strained 1,3-fused polycyclic cyclopropenes, 10, 11, and 12. The stereochemistry of the Diels-Alder reactions of cyclopropene 16 with furan and DPIBF are different. Cyclopropene 16 was treated with furan to form exo-exo and endo-exo adducts (5:2) and treated with DPIBF to generate an exo-exo adduct. Compounds 10, 11 and 12 undergo isomerization reactions to form benzaldehyde and phenyl 4-phenyl-[1]naphthyl ketone to release strain energies via diradical mechanisms.

PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES

On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.