18270-17-2

Basic information

• Product Name: 1-(TRIMETHYLSILYL)-1-PENTYNE
• Synonyms: 1-PENTYN-1-YLTRIMETHYLSILANE;1-(TRIMETHYLSILYL)-1-PENTYNE;TIMTEC-BB SBB009062;trimethyl(pent-1-ynyl)silane;1-TMS-1-pentyne 1-Pentyn-1-yltrimethylsilane;Trimethyl(pent-1-yn-1-yl)silane;TriMethylsilyl-1-pent
• CAS NO: 18270-17-2
• Molecular Formula: C₈H₁₆Si
• Molecular Weight: 140.3
• Product Categories: Alkynes;Building Blocks;Chemical Synthesis;Internal;Organic Building Blocks
• Mol File: 18270-17-2.mol

Chemical Properties

• Boiling Point: 135 °C(lit.)
• Flash Point: 73 °F
• Appearance: /
• Density: 0.765 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.73mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• BRN: 1744218
• CAS DataBase Reference: 1-(TRIMETHYLSILYL)-1-PENTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TRIMETHYLSILYL)-1-PENTYNE(18270-17-2)
• EPA Substance Registry System: 1-(TRIMETHYLSILYL)-1-PENTYNE(18270-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 18270-17-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
1-(Trimethylsilyl)-1-pentyne is used as a protecting agent for [application reason], allowing chemists to temporarily mask functional groups during the synthesis of complex organic compounds, preventing unwanted side reactions and facilitating the desired reaction pathways.
1-(Trimethylsilyl)-1-pentyne is also used as a reagent in the synthesis of more complex organic compounds for [application reason], contributing to the formation of new chemical bonds and structures, which are essential in the development of pharmaceuticals, materials, and other chemical products.
Used in Pharmaceutical Industry:
1-(Trimethylsilyl)-1-pentyne is used as a key intermediate in the synthesis of pharmaceutical compounds for [application reason], enabling the creation of new drug molecules with potential therapeutic applications.
Used in Material Science:
1-(Trimethylsilyl)-1-pentyne is used as a building block in the development of advanced materials for [application reason], such as polymers, coatings, and adhesives, where its unique properties can enhance performance and functionality.

InChI:InChI=1/C8H16Si/c1-5-6-7-8-9(2,3)4/h5-6H2,1-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 627-19-0 1-Pentyne 
• 14752-59-1 1-chloro-pent-1-yne 
• 14267-92-6 1-chloro-4-pentyne 
• 59323-36-3 1,2-dichloro-cyclopentene 
• 60-29-7 diethyl ether 
• 2696-32-4 but-3-en-1-ynyl-trimethyl-silane 
• 917-54-4 methyllithium 
• 75-79-6 Methyltrichlorosilane 
• 41246-05-3 pent-1-ynyl-magnesium bromide 
• 1066-54-2 trimethylsilylacetylene 
• 107-08-4 1-iodo-propane 

Downstream Products

• 56183-55-2 cis-1-Trimethylsilylpent-1-ene 
• 132796-97-5 Trimethyl-((Z)-1-phenyl-pent-1-enyl)-silane 
• 132796-98-6 [(Z)-1-(4-Methoxy-phenyl)-pent-1-enyl]-trimethyl-silane 
• 1733-15-9 Tetramethyl ethylenetetracarboxylate 
• 105937-50-6 2-methoxycarbonyle-7-trimethylsilyle hept-6-ynoate de methyle 
• 672263-60-4 1-chloro-4-(pent-1-yn-1-yl)benzene 
• 1150-26-1 N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 78629-78-4 Pt((CH₃)3SiC₂(C₃H₇))(P(C₆H₅)3)2 

Relevant articles and documents

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A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

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TETRASUBSTITUTED ALKENE COMPOUNDS AND THEIR USE

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Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives

A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.

Reactions of 1,2-dihalocycloalkenes with alkali metals in presence of chlorotrimethylsilane. Reductive carbon-carbon bond cleavage in five membered homocyclic system

1,2-Dihalocyclopentenes on reaction with alkali metals and chlorotrimethylsilane in hydrocarbon or ether solvents produce silylated 1-pentynes by ring opening. Sodium metal and hydrocarbon solvents favour the cleavage most. Different mechanistic aspects are considered.

AN UNUSUAL C-C BOND CLEAVAGE IN A FIVE MEMBERED RING

1,2-Dichlorocyclopentene undergoes dehalogenation-ring opening with sodium and chlorotrimethylsilane to form silylated pentynes.

Kinetic Evidence for the Formation of Discrete 1,4-Dehydrobenzene Intermediates. Trapping by Inter- and Intramolecular Hydrogen Atom Transfer and Observation of High-Temperature CIDNP

Upon being heated, alkyl-substituted cis-1,2-diethynyl olefins undergo cyclization to yield reactive 1,4-dehydrobenzenes; the products isolated may be derived from either unimolecular or bimolecular reactions of the intermediate. (Z)-4,5-Diethynyl-4-octene (4) undergoes rearrangement to yield 2,3-di-n-propyl-1,4-dehydrobenzene (17).Solution pyrolysis of 4 in inert aromatic solvent produces three unimolecular products, (Z)-dodeca-4,8-diyn-6-ene (7), benzocyclooctene (9), and o-allyl-n-propylbenzene (10), in high yield.When 1,4-cyclohexadiene is added to the pyrolysis solution as a trapping agent, high yields of the reduced product o-di-n-propylbenzene (12) are obtained.The kinetics of solution pyrolysis of 4 in the presence and absence of trapping agent establish that 2,3-di-n-propyl-1,4-dehydrobenzene is a discrete intermediate on the pathway leading to products.When the reaction was run in the heated probe of an NMR spectrometer, CIDNP was observed in 10.This observation, along with kinetic and chemical trapping evidence, indicates the presence of two additional intermediates, formed from 17 by squential intramolecular hydrogen transfer, on the pathway to products.The observation of CIDNP, coupled with the reactivity exhibited by 17 and the other two intermediates, implicates a biradical description of these molecules.Biradical 17 has been estimated to have a lifetime of about 10-9 s at 200 deg C and to lie in a well of about 5 kcal per mole with respect to the lowest energy unimolecular pathway ( hydrogen transfer).Ring opening (expected to be the lowest energy process for 1,4-dehydrobenzenes in which intramolecular hydrogen transfer is unlikely) to the isomeric diethynyl olefin 7 appears to have an activation enthalpy of about 10 kcal/mol.Upon thermal reaction in the gas phase (400 deg C) or in solution in inert solvents (Z)-2,3-diethylhexa-1,5-diyn-3-ene (5) rearranges in good yield to the isomeric diethynyl olefin (Z)-deca-3,7-diyn-5-ene (8) again presumably via 2,3-diethyl-1,4-dihydrobenzene 20 (addition of 1,4-cyclohexadiene to the reaction solution leads to a good yield of o-diethylbenzene, the expected trapping product of biradical 20).The absence of products due to intramolecular hydrogen transfer indicates that this process is at least 1 or 2 orders of magnitude slower than hydrogen transfer in 17.At 500 deg C in the gas phase products due to hydrogen transfer begin to appear.