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Sigma-Aldrich

3-Bromo-1-(trimethylsilyl)-1-propyne

98%

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Synonym(s):
3-(Trimethylsilyl)propargyl bromide, 3-Bromo-1-(trimethylsilyl)-1-propyne
Linear Formula:
BrCH2C≡CSi(CH3)3
CAS Number:
38002-45-8
Molecular Weight:
191.14
Beilstein:
2037650
MDL number:
MFCD00134460
PubChem Substance ID:
24863521
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.483 (lit.)

bp

44-45 °C/2 mmHg (lit.)

density

1.17 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C#CCBr

InChI

1S/C6H11BrSi/c1-8(2,3)6-4-5-7/h5H2,1-3H3

InChI key

GAPRPFRDVCCCHR-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
A Convenient Propargylating Agent. 3-Bromo-1-Trimethylisilyl-1-Propyne.
Miller RB.
Synthetic Communications, 2(5), 267-272 (1972)
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.
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)
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