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348007

Sigma-Aldrich

1-Trimethylsilyl-1-hexyne

99%

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About This Item

Linear Formula:
CH3(CH2)3C≡CSi(CH3)3
CAS Number:
3844-94-8
Molecular Weight:
154.32
Beilstein/REAXYS Number:
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

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

122.0 °F - closed cup

flash_point_c

50 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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’.

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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
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)

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