18243-59-9

Basic information

• Product Name: (bromoethynyl)(trimethyl)silane
• Synonyms: (Bromoethynyl)(trimethyl)silane; Ethyne, 1-bromo-2-trimethylsilyl-
• CAS NO: 18243-59-9
• Molecular Formula: C₅H₉BrSi
• Molecular Weight: 177.1145
• Mol File: 18243-59-9.mol

Chemical Properties

• Boiling Point: 123.7°C at 760 mmHg
• Flash Point: 21°C
• Density: 1.236g/cm³
• Vapor Pressure: 15.9mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: (bromoethynyl)(trimethyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: (bromoethynyl)(trimethyl)silane(18243-59-9)
• EPA Substance Registry System: (bromoethynyl)(trimethyl)silane(18243-59-9)

Safety Data

• Hazardous Substances Data: 18243-59-9(Hazardous Substances Data)

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 75-61-6 dibromodifluoromethane 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 109-72-8 n-butyllithium 

Downstream Products

• 38177-56-9 trimethyl(4-phenylbuta-1,3-diyn-1-yl)silane 
• 16387-71-6 deca-4,6-diyne 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 19024-47-6 1-Trimethylsilyl-1,3-heptadiyne 
• 85678-39-3 1-[4-(trimethylsilyl)-1,3-butadiyn-1-yl]cyclohexene 
• 84751-19-9 1-trimethylsilyl-4-t-butyl-1,3-butadiyne 
• 84751-18-8 (4-Cyclohexyl-buta-1,3-diynyl)-trimethyl-silane 

Relevant articles and documents

Synthesis of potentially biologically active 6-(1,3-butadiynyl)purines

1,3-Alkadiynyl(trimethyl)silanes were prepared by the Negishi or Sonogashira reactions of bromoethynyl (trimethyl)silane with several terminal alkynes in 34-75% yield. However, the direct Hiyama coupling of these compounds with 6-iodopurine derivatives ha

An efficient synthesis of difluoropropargyl bromides

High yields of γ-alkyl, -silyl and -aryl-substituted difluoropropargyl bromides have been obtained by monitoring concentration and temperature in the reaction between CF2Br2 and γ-substituted lithium acetylide. γ-Silyl substituents afforded the corresponding α,α,α-difluorobromopropargyl alcohols in good yields via cleavage of tetrabutylammonium fluoride in the presence of an aldehyde. Georg Thieme Verlag Stuttgart.

Stereoselective synthesis of (E)- and (Z)-acetals of pent-2-en-4-yn-1-al and related dienynes and dienediynes

(3E)-5,5-Diethoxypent-3-en-1-yne was stereospecifically prepared by Sonogashira-Linstrumelle cross-coupling between (E)-3-iodoacrolein diethylacetal and (trimethylsilyl)acetylene. The (Z) isomer was obtained by Stille cross-coupling between the corresponding (Z)-vinyltin and 1-bromo-2- (trimethylsilyl)acetylene. In the case of the (E) isomer, transacetalisation occurred without isomerization affording a large variety of (E)-enynals protected as acetals. It has also been shown to be possible to obtain the corresponding (E,E)-dienediyne through sp-sp homo-coupling under appropriate experimental conditions.

Synthesis of Thiomorpholin-3-ones by a Gold-Catalysed Oxidative Cyclisation-Rearrangement Cascade from Ynamides

A gold-catalyzed oxidative N-cyclisation strategy allows for the preparation of α-aryl thiomorpholin-3-ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]- or [1,2]-sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N-oxide oxidant with an IPrAuCl-derived catalyst.

Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines

A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated azomethine ylides induced by the chiral catalyst. A range of amino acyloxyenamides are delivered in moderate to good yields with good ee values. In addition, a possible catalytic cycle with a transition model is proposed to elucidate the reaction mechanism.

Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

SOLAR CELL DYES FOR COPPER REDOX BASED DYE SENSITIZED SOLAR CELLS AND COMBINATIONS THEREOF

The present application discloses compounds and compositions, useful in the manufacture of dye-sensitized solar cells and other similar technology.

Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides

A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.

SOLAR CELL DYES FOR COPPER REDOX BASED DYE SENSITIZED SOLAR CELLS AND COMBINATIONS THEREOF

The present application discloses compounds and compositions, useful in the manufacture of dye-sensitized solar cells and other similar technology.

PYRROLO[2,3-D]PYRIMIDIN-2-ONE ANTIMICROBIAL COMPOUNDS

The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. In some embodiments, the present disclosure provides pyrrolo[2,3-d]pyrimidin-2-ones useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals.