17889-43-9

Basic information

• Product Name: 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)
• Synonyms: TIMTEC-BB SBB009127;(+/-) 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL;3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL;3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)
• CAS NO: 17889-43-9
• Molecular Formula: C₉H₁₈OSi
• Molecular Weight: 170.32
• Mol File: 17889-43-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 326.6°C at 760 mmHg
• Flash Point: 151.3°C
• Appearance: /
• Density: 0.844
• Vapor Pressure: 0.000213mmHg at 25°C
• Refractive Index: 1.439
• CAS DataBase Reference: 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)(17889-43-9)
• EPA Substance Registry System: 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)(17889-43-9)

Safety Data

• Hazardous Substances Data: 17889-43-9(Hazardous Substances Data)

Usage

General Description

3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-) is a chemical compound that consists of a pentynol with a trimethylsilyl group and a methyl substituent. It is used in organic synthesis as a building block for the preparation of various compounds, such as pharmaceuticals and agrochemicals. The addition of the trimethylsilyl group enhances the reactivity and stability of the compound, making it a valuable intermediate in organic chemistry. Its versatile nature and functional groups make it a useful tool for creating complex molecular structures. The (+/-) designation indicates that the compound is a racemic mixture, meaning it contains equal amounts of both enantiomers.

InChI:InChI=1/C12H24N2OSi2/c1-16(2,11-7-5-9-13)15-17(3,4)12-8-6-10-14/h5-8,11-12H2,1-4H3

Upstream product

• 78-93-3 butanone 
• 1066-54-2 trimethylsilylacetylene 
• 61210-52-4 (trimethylsilyl)ethynylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 77-75-8 meparfynol 

Downstream Products

• 77-75-8 meparfynol 
• 351523-44-9 (1-ethyl-1-methyl-allyl)-phenyl-amine 
• 14465-46-4 N-(3-methylpent-1-yn-3-yl)aniline 

Relevant articles and documents

Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration

This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.

1,6-bis(trimethylsilyl)-3,3,3,4-tetraalkylhexa-1,5-diynes

Silylacetylene chlorides Me3SiCCCRR'Cl react with magnesium in ether medium to give the corresponding 1,6-bis(trimethylsilyl)-3,3,4,4-tetraalkylhexa-1,5-diynes.By the same method bis(1-trimethylsilylethynylcyclopent-1-yl) and bis(1-trimethylsilylethynylcyclohex-1-yl) were prepared.Desilylation of 1,6-bis(trimethylsilyl)-3,3,4,4-tetraalkylhexa-1,5-diynes gives corresponding 3,3,4,4-tetraalkylhexa-1,5-diynes.