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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:
Molecular Weight:
191.14
Beilstein/REAXYS Number:
2037650
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
376264333557143065
vibrant-m

376264

Trimethyl(propargyl)silane

vibrant-m

333557

(1-Bromovinyl)trimethylsilane

vibrant-m

143065

3-Dimethylamino-1-propyne

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

refractive index

n20/D 1.483 (lit.)

refractive index

n20/D 1.413 (lit.)

refractive index

n20/D 1.458 (lit.)

refractive index

n20/D 1.419 (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

density

1.17 g/mL at 25 °C (lit.)

density

0.753 g/mL at 25 °C (lit.)

density

1.156 g/mL at 25 °C (lit.)

density

0.772 g/mL at 25 °C (lit.)

bp

44-45 °C/2 mmHg (lit.)

bp

91-93 °C (lit.)

bp

124 °C/745 mmHg (lit.)

bp

79-83 °C (lit.)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

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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Sum P-E and Weiler L.
Canadian Journal of Chemistry, 56(17), 2301-2304 (1978)
A Convenient Propargylating Agent. 3-Bromo-1-Trimethylisilyl-1-Propyne.
Miller RB.
Synthetic Communications, 2(5), 267-272 (1972)

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