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403482

Sigma-Aldrich

3-(Trimethylsilyl)propynoic acid

98%

Synonym(s):

3-(Trimethylsilyl)propiolic acid

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About This Item

Linear Formula:
(CH3)3SiC≡CCO2H
CAS Number:
5683-31-8
Molecular Weight:
142.23
Beilstein:
1755674
MDL number:
MFCD00190216
UNSPSC Code:
12352100
PubChem Substance ID:
24865196
NACRES:
NA.22

Assay

98%

bp

105-110 °C/10 mmHg (lit.)

mp

47-49 °C (lit.)

functional group

carboxylic acid

SMILES string

C[Si](C)(C)C#CC(O)=O

InChI

1S/C6H10O2Si/c1-9(2,3)5-4-6(7)8/h1-3H3,(H,7,8)

InChI key

IPEATTYBFBRNEB-UHFFFAOYSA-N

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Application

3-(Trimethylsilyl)propynoic acid (3-(Trimethylsilyl)propiolic acid) may be used as starting reagent for the synthesis of 3-trimethylsilylpropynamides.
3-(Trimethylsilyl)propynoic acid may be used in the regioselective preparation of 1,5-trisubstituted 1H-1,2,3-triazoles.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD9168
MKBT0503V
MKBK0732V
MKBH6356V
MKBC2606

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One-Pot Synthesis of 3-(Trimethylsilyl) propynamides.
Medvedeva AS, et al.
Russ. J. Org. Chem., 46(10), 1466-1470 (2010)
Steven J Coats et al.
Organic letters, 7(8), 1469-1472 (2005-04-09)
[reaction: see text] A regioselective method for the preparation of 1,5-trisubstituted 1H-1,2,3-triazoles via a 1,3-dipolar cycloaddition of 1-trimethylsilylacetylenes with organoazides is described. Immobilization of the azide on REM resin and subsequent cycloaddition afforded a 2 x 2 x 4 x
Yevgen Matviychuk et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 319, 106814-106814 (2020-09-20)
Low-cost, user-friendly benchtop NMR instruments are often touted as a "one-click" solution for data acquisition, however insufficient peak dispersion in their spectra often reduces the accuracy of quantification and requires user expertise with sophisticated processing tools. Our work aims to

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