377775
3-Bromo-1-(trimethylsilyl)-1-propyne
98%
Synonym(s):
3-(Trimethylsilyl)propargyl bromide, 3-Bromo-1-(trimethylsilyl)-1-propyne
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About This Item
Linear Formula:
BrCH2C≡CSi(CH3)3
CAS Number:
Molecular Weight:
191.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2037650
Assay:
98%
Form:
liquid
InChI
1S/C6H11BrSi/c1-8(2,3)6-4-5-7/h5H2,1-3H3
SMILES string
C[Si](C)(C)C#CCBr
InChI key
GAPRPFRDVCCCHR-UHFFFAOYSA-N
assay
98%
form
liquid
refractive index
n20/D 1.483 (lit.)
Quality Level
density
1.17 g/mL at 25 °C (lit.)
functional group
bromo
storage temp.
2-8°C
Related Categories
General description
3-Bromo-1-(trimethylsilyl)-1-propyne is reported as a propargylating agent. Selective reaction of 3-bromo-1-(trimethylsilyl)-1-propyne with α-keto ester using indium metal has been studied.
Application
3-Bromo-1-(trimethylsilyl)-1-propyne may be used in the preparation of tetrahydroisoquinoline-3-carboxylic acid derivatives. It may be used as reagent for the alkylation of dianion of β-keto esters at γ-carbon. It may be employed in the preparation of terminal conjugated enynes and allenic alcohols.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
145.4 °F - closed cup
flash_point_c
63 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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S Kotha et al.
Bioorganic & medicinal chemistry letters, 10(13), 1413-1415 (2000-07-11)
Tetrahydroisoquinoline-3-carboxylic acid derivatives are prepared via a [2 + 2 + 2] cycloaddition reaction as a key step using Wilkinson's and CpCo(CO)2 catalysts.
A convenient allylation of 1, n-dicarbonyl compounds using organoindium reagents.
Lee PH, et al.
Bull. Korean Chem. Soc., 22(12), 2301-2304 (2001)
Synthesis, 414-414 (1991)
Utilization of trimethylsilylpropyne as an acetonyl unit in the synthesis of cyclopentenones. Applications to the synthesis of jasmone and dihydrojasmone. Can
Sum P-E and Weiler L.
Canadian Journal of Chemistry, 56(17), 2301-2304 (1978)
Liebigs Ann. Chem., 673-673 (1994)
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