41309-43-7

Basic information

• Product Name: 2-(BROMOVINYL)TRIMETHYLSILANE
• Synonyms: (E)-2-(Trimethylsilyl)vinyl bromide;trans-1-Bromo-2-(trimethylsilyl)ethene;(2-BroMovinyl)triMethylsilane approx. 90% trans, 98%;(2-BROMOVINYL)TRIMETHYLSILANE, 98%, PRED OMINANTLY TRANS;(2-BROMOVINYL)TRIMETHYLSILANE(CIS+TRANS);β-(Trimethylsilyl)vinyl bromide, 1-Bromo-2-(trimethylsilyl)ethylene;[(E)-2-BroMovinyl](triMethyl)silane;(E)-(2-Bromoethenyl)trimethylsilane
• CAS NO: 41309-43-7
• Molecular Formula: C₅H₁₁BrSi
• Molecular Weight: 179.13034
• Product Categories: Alkenyl;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 41309-43-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 50-51 °C52 mm Hg(lit.)
• Flash Point: 85 °F
• Appearance: /
• Density: 1.167 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: 2-8°C
• BRN: 1700085
• CAS DataBase Reference: 2-(BROMOVINYL)TRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BROMOVINYL)TRIMETHYLSILANE(41309-43-7)
• EPA Substance Registry System: 2-(BROMOVINYL)TRIMETHYLSILANE(41309-43-7)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 41309-43-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(Bromovinyl)trimethylsilane is used as a reagent for the preparation of vinylsilanes, which are essential building blocks in the synthesis of complex organic compounds. Its application in palladium-catalyzed coupling reactions with nucleophiles allows for the creation of a wide range of functionalized organic molecules.
Used in Pharmaceutical and Agrochemical Development:
In the pharmaceutical and agrochemical industries, 2-(Bromovinyl)trimethylsilane is utilized as a key intermediate in the synthesis of various compounds. Its unique chemical properties enable the development of new and innovative drugs and agrochemicals, contributing to advancements in these fields.
Used in Cross-Coupling Reactions:
2-(Bromovinyl)trimethylsilane is employed as a cross-coupling reagent in the synthesis of functionalized organic molecules. Its ability to participate in cross-coupling reactions with different nucleophiles expands the scope of organic synthesis, allowing for the creation of diverse and complex molecular structures.

Upstream product

• 13852-33-0 (2-bromo-vinyl)-trichloro-silane 
• 676-58-4 methylmagnesium chloride 
• 1066-54-2 trimethylsilylacetylene 
• 18881-62-4 1,2-dibromo-1,2-bis-trimethylsilanyl-ethane 
• 18178-59-1 (E)-1,2-bis(trimethylsilyl)ethene 
• 70737-20-1 (cis-2-bromo-vinyl)-trimethyl-silane 

Downstream Products

• 22500-95-4 (E)-1,3-bis(trimethylsilyl)-1,3-butadiene 
• 65108-79-4 trans,trans-1,5-Bis-(trimethylsinyl)-1,4-pentadien-3-on 
• 22430-48-4 (1E,3E)-1-trimethylsilyl-5,5-dimethyl-1,3-hexadiene 
• 71779-75-4 (E)-1-(trimethylsilyl)-1-decene 
• 22430-47-3 (1E,3E)-1,4-bis(trimethylsilyl)-1,3-butadiene 
• 126204-79-3 <2-(2-furyl)ethenyl>trimethylsilane 
• 119930-36-8 methyl-((1-phenyl-3-trimethylsilyl)-2E-propenyl)carbonate 
• 197526-52-6 1-((E)-1-Ethoxy-5-trimethylsilanyl-pent-4-en-2-ynyl)-1H-benzotriazole 
• 13703-52-1 1-phenyl-1,4-cyclohexadiene 
• 57415-83-5 (E)-diphenyl[2-(trimethylsilyl)ethenyl]phosphane oxide 
• 70737-20-1 (cis-2-bromo-vinyl)-trimethyl-silane 
• 126231-52-5 (E)-1-trimethylsilyl-4-(1-cyclohexenyl)-1-buten-3-yne 
• 70960-90-6 trimethyl-nona-1,3t-dien-t-yl-silane 
• 120501-74-8 (E)-1-trimethylsilyl-1-nonen-3-yne 

Relevant articles and documents

Pentacyclic furanosteroids: The synthesis of potential kinase inhibitors related to viridin and wortmannolone

(Chemical Equation Presented) A regiocontrolled intermolecular Diels-Alder reaction of an o-benzoquinone followed by an intramolecular nitrile oxide cyclization is employed to prepare the BCD fragment of viridin. The AE segment is attached to it by means of an intramolecular Diels-Alder reaction of an o-benzoquinone monoketal generated in situ from tricycle 15 and 5-trimethylsilyl-2E,4E-pentadienol 20. The silyl substituent at C-1 of the pentacyclic product directs the dihydroxylation of the C2-C 3 double bond to its β-face. Various transformations of the 1α-trimethylsilyl-2β,3β-dihydroxy pentacycle into several others with oxygen substituents in ring A are described. One of these products 40 possesses the same structure and relative stereochemistry in rings A, B, and E as that of the natural product wortmannolone 3.

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.

Control over the relative stereochemistry at C4 and C5 of 4,5-dihydrooxepins through the cope rearrangement of 2,3-divinyl epoxides and a conformational analysis of this ring system

The Cope rearrangement of cis-2,3-divinyl epoxides was used to control the relative stereochemistry at C4 and C5 of 4,5-dihydrooxepins. Wadsworth-Horner-Emmons olefination of either (4E)-cis-2,3-epoxy-5-(trimethylsilyl)-4-pentenal (3) or (5E)-cis-3,4-epoxy-6-(trimethylsiIyl)-5-hexen-2-one (4) provided the cis epoxides used in this study. The termini of their 1,5-dienes were thereby substituted at one end with a trimethylsilyl group with fixed E stereochemistry and at the other with either a carboalkoxy or cyano substituent as both the Z and E isomers. The rearrangements were carried out within a temperature range of 95-135°C, and all of the rearrangements were stereospecific, each leading to a single 4,5-dihydrooxepin. Based on a presumed boatlike transition state for these rearrangements, the (1E,5E)-cis-3,4-epoxy-1,5-hexadienes 5a-e led to the cis-4,5-dihydrooxepins 7a-e, and the (1E,5Z)-cis-3,4-epoxy-1,5-hexadienes 6a,c-e led to the trans-4,5-dihydrooxepins 8a,c-e. In general, those 1,5-dienes containing a Z double bond rearranged slower than the corresponding E isomers. A solvent affect was found in the [3,3] sigmatropic rearrangement of substrates containing Z-α,β-unsaturated esters, CH3CN being a more effective solvent than CCl4. It was further found that Z-α,β-unsaturated nitiriles rearranged more cleanly than the corresponding esters. The relative stereochemistry at C4 and C5 can greatly affect the subsequent reactivity of the oxepin nucleus, as illustrated by the greater kinetic acidity of the cis isomer of 4-carbomethoxy-5-(trimethylsilyl)-4,5-dihydrooxepin (7a) compared to that of its trans isomer 8a. The ester of the former compound was easily deprotonated at -70°C in THF by LiN(TMS)2 and the resultant enolate alkylated at the α carbon by MeI, conditions that led to the complete recovery of the trans isomer. These results are consistent with the assignment of cis and trans stereochemistry of these oxepins. From their 1H NMR spectra, all of the trans-4,5-dihydrooxepins appeared to be similar to each other in terms of their coupling patterns and constants, but the cis-4,5-dihydrooxepins could be divided up into two groups on the basis of their coupling constants. For three of the oxepins, cis-4,5-dihydrooxepins 7a and 7c and trans-4,5-dihydrooxepin 8a, the assignment of their coupling patterns was confirmed by 2-D NMR. The minimum-energy conformations of these three oxepins were determined by molecular mechanics calculations. The conformational preferences were explicable in terms of two steric interactions: allylic A1,2 strain and the gauche interaction at C4 and C5.