Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

348007

Sigma-Aldrich

1-Trimethylsilyl-1-hexyne

99%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CH3(CH2)3C≡CSi(CH3)3
CAS Number:
3844-94-8
Molecular Weight:
154.32
Beilstein:
1421652
MDL number:
MFCD00075407
UNSPSC Code:
12352100
PubChem Substance ID:
24861541
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.431 (lit.)

bp

65 °C/35 mmHg (lit.)

density

0.764 g/mL at 25 °C (lit.)

SMILES string

CCCCC#C[Si](C)(C)C

InChI

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

InChI key

SFCRJYVNDZSYCT-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

1-Trimethylsilyl-1-hexyne is a trialkylsilylalkyne. Tetrabutylammonium fluoride (TBAF) catalyzed conversion of 1-trimethylsilyl-1-hexyne to corresponding propargylic alcohol is reported. Pd(OAc)2/L‚ HCl-catalyzed Sonogashira coupling reaction of aryl bromide with 1-trimethylsilyl-1-hexyne has been reported.

Application

1-Trimethylsilyl-1-hexyne may be used in the preparation of enynes by coupling with vinyl triflates or aryl iodide using silver salt and Pd(PPh3)4 as catalyst. It may be used in the preparation of functionalised durene and isodurene derivatives.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

122.0 °F - closed cup

Flash Point(C)

50 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

A new mild procedure for the direct coupling of 1-trimethylsilyl acetylenes with vinyl triflates or aryl iodide.
Halbes U and Pale P.
Tetrahedron Letters, 43(11), 2039-2042 (2002)
Efficient Sonogashira reactions of aryl bromides with alkynylsilanes catalyzed by a palladium/imidazolium salt system.
Yang C and Nolan SP.
Organometallics, 21(6), 1020-1022 (2002)
An efficient cobalt catalyst for the neutral Diels-Alder reaction of acyclic 1, 3-dienes with internal alkynes.
Hilt G and Korn TJ.
Tetrahedron Letters, 42(15), 2783-2785 (2001)
Venkat Reddy Chintareddy et al.
The Journal of organic chemistry, 76(11), 4482-4488 (2011-04-27)
Herein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and operationally simple, and a variety

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service