208264
Allyltrimethylsilane
98%
Synonym(s):
3-(Trimethylsilyl)propene
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About This Item
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Quality Level
assay
98%
form
liquid
refractive index
n20/D 1.407 (lit.)
bp
84-88 °C (lit.)
density
0.719 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C[Si](C)(C)CC=C
InChI
1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3
InChI key
HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Application
Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi−Sakurai reaction.
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2 - Skin Irrit. 2
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
60.8 °F - closed cup
flash_point_c
16 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Organic letters, 5(24), 4639-4640 (2003-11-25)
[reaction: see text] Direct allylation of glycal-derived donor-acceptor cyclopropanes has been achieved with TiCl(4) activation followed by addition of allyltrimethylsilane. The alpha diastereomer is the major product, with selectivities ranging from 3:1 to 10:1 and yields around 80%.
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