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687170

Sigma-Aldrich

3-(Trimethylsilyl)-2-propynal

97%

Synonym(s):

(Trimethylsilyl)propiolaldehyde

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About This Item

Empirical Formula (Hill Notation):
C6H10OSi
CAS Number:
2975-46-4
Molecular Weight:
126.23
MDL number:
MFCD01103709
UNSPSC Code:
12352100
PubChem Substance ID:
329761107
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.444

density

0.854 g/mL at 25 °C

functional group

aldehyde

storage temp.

2-8°C

SMILES string

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

InChI

1S/C6H10OSi/c1-8(2,3)6-4-5-7/h5H,1-3H3

InChI key

LJRWLSKYGWLYIM-UHFFFAOYSA-N

Application

3-(Trimethylsilyl)-2-propynal can be used as a reactant to synthesize:
  • Silicon-containing polyfunctional chiral tertiary phosphine oxides, which are employed as building blocks to prepare polydentate amphiphilic ligands for the design of novel metal complex catalysts.[1]
  • 4-trimethylsilyl-1H-1,2,3-triazole-5-carbaldehyde by reacting with trimethylsilyl azide.[2]
  • 4-trimethylsilylethynyl-4H-pyran-3,5-dicarbaldehyde via trimerization reaction in the presence of DABCO (1,4-diazabicyclo-[2.2.2]octane) as a catalyst.[3]

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

84.9 °F

flash_point_c

29.4 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN4362
MKCL8780
MKCH7536
MKBV9938V
MKBN3684V

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Detection by 1 H NMR of malonaldehyde as the key intermediate in the trimerization of 3-trimethylsilylprop-2-ynal to 4-trimethylsilylethynyl-4 H-pyran-3, 5-dicarbaldehyde
Mareev AV, et al.
Russ. J. Org. Chem., 44(10), 1551-1553 (2008)
1, 3-dipolar cycloaddition of trimethylsilyl azide to propynals and dimerization of 1H-1, 2, 3-triazole-5-carbaldehydes to tricyclic bis-hemiaminals
Demina MM, et al.
Russ. J. Org. Chem., 40(12), 1804-1809 (2004)
Regioselective addition of secondary phosphine oxides to 3-(trialkylsilyl)-and 3-(trialkylgermyl)-2-propynals
Gusarova NK, et al.
Journal of Organometallic Chemistry, 659(1-2), 172-175 (2002)

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