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About This Item
Linear Formula:
CH3(CH2)3C≡CSi(CH3)3
CAS Number:
Molecular Weight:
154.32
Beilstein:
1421652
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Regulatory Information
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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)
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
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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