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377775

Sigma-Aldrich

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
Beilstein:
2037650
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

Signal Word

Warning

Hazard Statements

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

377775-BULK:
377775-1G:
377775-VAR:
377775-10G:


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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.
Liebigs Ann. Chem., 673-673 (1994)
Synthesis, 414-414 (1991)
A Convenient Propargylating Agent. 3-Bromo-1-Trimethylisilyl-1-Propyne.
Miller RB.
Synthetic Communications, 2(5), 267-272 (1972)
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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