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About This Item
Linear Formula:
CH3(CH2)3C≡CSi(CH3)3
CAS Number:
Molecular Weight:
154.32
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1421652
Assay:
99%
InChI
1S/C9H18Si/c1-5-6-7-8-9-10(2,3)4/h5-7H2,1-4H3
SMILES string
CCCCC#C[Si](C)(C)C
InChI key
SFCRJYVNDZSYCT-UHFFFAOYSA-N
assay
99%
refractive index
n20/D 1.431 (lit.)
bp
65 °C/35 mmHg (lit.)
density
0.764 g/mL at 25 °C (lit.)
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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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
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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
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)
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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