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Merck
CN

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:
38002-45-8
Molecular Weight:
191.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863521
MDL number:
MFCD00134460
Beilstein/REAXYS Number:
2037650

Key Documents

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Product Name

3-Bromo-1-(trimethylsilyl)-1-propyne, 98%

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.)

bp

44-45 °C/2 mmHg (lit.)

density

1.17 g/mL at 25 °C (lit.)

functional group

bromo

storage temp.

2-8°C

Quality Level

100

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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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3343
MKBW2560V
MKBV1251V
MKBK4851V
MKBG6151V

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A Convenient Propargylating Agent. 3-Bromo-1-Trimethylisilyl-1-Propyne.
Miller RB.
Synthetic Communications, 2(5), 267-272 (1972)
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)
Liebigs Ann. Chem., 673-673 (1994)
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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