3844-94-8

Basic information

• Product Name: 1-Trimethylsilyl-1-hexyne
• Synonyms: 1-HEXYN-1-YLTRIMETHYLSILANE;1-TRIMETHYSILYL-1-HEXYNE;1-TRIMETHYLSILYL-1-HEXYNE;TIMTEC-BB SBB009058;1-Trimethyl;(1-Hexynyl)trimethylsilane;1-Hexynyltrimethylsilane;Trimethyl(1-hexynyl)silane
• CAS NO: 3844-94-8
• Molecular Formula: C₉H₁₈Si
• Molecular Weight: 154.32
• Product Categories: Alkynes;Internal;Organic Building Blocks
• Mol File: 3844-94-8.mol

Chemical Properties

• Boiling Point: 65 °C35 mm Hg(lit.)
• Flash Point: 99 °F
• Appearance: /
• Density: 0.764 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.25mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• BRN: 1421652
• CAS DataBase Reference: 1-Trimethylsilyl-1-hexyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Trimethylsilyl-1-hexyne(3844-94-8)
• EPA Substance Registry System: 1-Trimethylsilyl-1-hexyne(3844-94-8)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 3844-94-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Trimethylsilyl-1-hexyne is used as a building block for the construction of complex organic molecules, due to its ability to participate in various chemical transformations, including cross-coupling reactions and metal-catalyzed reactions.
Used in Protecting Groups for Alkynes:
In organic chemistry, 1-Trimethylsilyl-1-hexyne is used as a protecting group for alkynes, allowing chemists to temporarily mask the reactivity of the alkyne moiety. This protection is advantageous for reactions where the alkyne group should not participate, and the trimethylsilyl group can be removed under mild conditions to reveal the terminal alkyne functionality, thus controlling the reactivity and selectivity of the molecule.
Used in Chemical Transformations:
1-Trimethylsilyl-1-hexyne is utilized in a variety of chemical transformations to facilitate the synthesis of desired products. Its stability and reactivity make it an ideal candidate for reactions that require the manipulation of alkyne-containing compounds without unwanted side reactions.

InChI:InChI=1/C9H18Si/c1-5-6-7-8-9-10(2,3)4/h5-7H2,1-4H3

Upstream product

• 32359-01-6 hexenylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 693-02-7 hex-1-yne 
• 1116-61-6 tripropylborane 
• 72096-98-1 trimethyl(3-phenoxy-1-propynyl)silane 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 7677-24-9 trimethylsilyl cyanide 
• 17689-03-1 1-hexynyllithium 
• 993-07-7 trimethylsilan 
• 16029-98-4 trimethylsilyl iodide 
• 18244-40-1 4-iodobutoxy-trimethyl-silane 
• 91656-99-4 (5-bromo-pent-1-ynyl)-trimehyl-silane 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 18243-59-9 (2-bromoethynyl)trimethylsilane 

Downstream Products

• 52835-06-0 (Z)-hex-1-enyl(trimethyl)silane 
• 54731-58-7 (E)-1-trimethylsilyl-1-hexene 
• 6395-83-1 α-keto methyl hexanoate 
• 83182-69-8 4-Butyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 1733-15-9 Tetramethyl ethylenetetracarboxylate 
• 105937-43-7 dimethyl ester of 1-butyl-2-(trimethylsilyl)cyclopropene-3,3-dicarboxylic acid 
• 155623-79-3 (E)-1-(phenylseleno)-1-(trimethylsilyl)-1-hexene 
• 144115-74-2 2-butyl-4-(phenoxymethyl)-1-(trimethylsilyl)-1,4-pentadiene 
• 144823-68-7 (E)-2-Dimethyl(phenyl)silyl-1-trimethylsilylhexene 
• 113964-35-5 1-butyl-4-methylene-2-(trimethylsilyl)-1-cyclopentene 
• 420-56-4 trimethylsilyl fluoride 
• 186182-74-1 1-hexyne 

Relevant articles and documents

Thermal [3,3]-rearrangement of 1,1-disubstituted allyl carboxylates: Lone pair participation and the geminal bond participation

The diastereoselectivity of the [3,3]-rearrangement of 1,1-disubsstituted allyl carboxylates was studied. In this heteroatom-containing system, the transition state has a boat-like transition structure (TS) because of the participation of the lone pairs and the secondary orbital interaction. Although the TS for the [1,3]-rearrangement has a far higher barrier, it does not proceed in the usual antarafacial manner due to the cyclic orbital interaction among two lone pairs of the carboxylate and the allylic lumo. In conjunction with the geminal bond participation, delocalization to the σ-bond at the Z-position shows a bonding character in the transition state of the [3,3]-rearrangement. Therefore, we predicted that a more electron-withdrawing σ-bond prefers the Z-position in the product. We designed the 1,1-disubstituted substrates with trimethylsilyl and pentyl groups, and found that the trimethylsilyl group prefers the Z-position despite its steric bulkiness. We confirmed our prediction by experimentation. This Z-selectivity was improved when a trimethylgermyl group was used.

General Enantioselective and Stereochemically Divergent Four-Stage Approach to Fused Tetracyclic Terpenoid Systems

Tetracyclic terpenoid-derived natural products are a broad class of medically relevant agents that include well-known steroid hormones and related structures, as well as more synthetically challenging congeners such as limonoids, cardenolides, lanostanes, and cucurbitanes, among others. These structurally related compound classes present synthetically disparate challenges based, in part, on the position and stereochemistry of the numerous quaternary carbon centers that are common to their tetracyclic skeletons. While de novo syntheses of such targets have been a topic of great interest for over 50 years, semisynthesis is often how synthetic variants of these natural products are explored as biologically relevant materials and how such agents are further matured as therapeutics. Here, focus was directed at establishing an efficient, stereoselective, and molecularly flexible de novo synthetic approach that could offer what semisynthetic approaches do not. In short, a unified strategy to access common molecular features of these natural product families is described that proceeds in four stages: (1) conversion of epichlorohydrin to stereodefined enynes, (2) metallacycle-mediated annulative cross-coupling to generate highly substituted hydrindanes, (3) tetracycle formation by stereoselective forging of the C9-C10 bond, and (4) group-selective oxidative rearrangement that repositions a quaternary center from C9 to C10. These studies have defined the structural features required for highly stereoselective C9-C10 bond formation and document the generality of this four-stage synthetic strategy to access a range of unique stereodefined systems, many of which bear stereochemistry/substitution/functionality not readily accessible from semisynthesis.

Synthesis of cis-β-Amidevinyl Benziodoxolones from the Ethynyl Benziodoxolone-Chloroform Complex and Sulfonamides

The synthesis of cis-β-amidevinyl benziodoxolones from the ethynyl benziodoxolone-chloroform complex and sulfonamides is reported. Evidence indicates that highly reactive unsubstituted ethynyl benziodoxolone undergoes Michael addition of sulfonamides, including sterically demanding acyclic amino acid derivatives. The synthesis of selectively deuterated cis-β-amidevinyl benziodoxolones and investigation of ethynyl-λ3-iodane reactivity are also described.

Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis

Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple

Influence of molecular length on the adsorption of linear trimethylsilylacetylene derivatives at the n-tetradecane/Au(111) interface: Chemisorption vs. Physisorption

Adsorption of two trimethylsilylacetylene (TMSA) derivatives bearing linear alkyl chains of different lengths has been studied at the n-tetradecane/Au(111) interface. The lying or standing orientation of TMSA compounds on the gold surface shows that adsorption is not only controlled by the chemical reactivity of the molecules but also by their size.

Z-Selective ring opening of vinyl oxetanes with dialkyl dithiophosphate nucleophiles

Dialkyl dithiophosphates selectively ring open vinyl oxetanes in excellent yields under mild reaction conditions to form useful allylic thiophosphate products with high Z-selectivity. The Royal Society of Chemistry 2013.

Rapid consecutive three-component coupling-Fiesselmann synthesis of luminescent 2,4-disubstituted thiophenes and oligothiophenes

(Hetero)aroyl chlorides, alkynes, and ethyl 2-mercapto acetate can be reacted in a consecutive three-component synthesis to give 2,4-disubstituted thiophene 5-carboxylates in good to excellent yields. In the sense of a pseudo-five-component reaction highly blue luminescent symmetrical terthiophenes and a quinquethiophene can be synthesized in excellent yield.

Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents

A highly efficient alkyl-alkynyl coupling system is described which is promoted by a well-defined and moisture-stable pincer complex [NiCl{C 6H3-2,6-(OPPh2)2}] (1). Non-activated alkyl halides could be efficient

Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides

(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.

Platinum-catalyzed nucleophilic addition of vinylsilanes at the β-position

In the presence of catalytic amounts of PtCl2 and metal Iodides, β-substituted vlnylsllanes reacted with aldehydes at the β-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl 2 and Mnl2 was found to be effective In addition to aliphatic aldehydes.