687170
3-(Trimethylsilyl)-2-propynal
97%
Synonym(s):
(Trimethylsilyl)propiolaldehyde
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About This Item
Empirical Formula (Hill Notation):
C6H10OSi
CAS Number:
Molecular Weight:
126.23
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
Form:
liquid
Product Name
3-(Trimethylsilyl)-2-propynal, 97%
InChI
1S/C6H10OSi/c1-8(2,3)6-4-5-7/h5H,1-3H3
SMILES string
C[Si](C)(C)C#CC=O
InChI key
LJRWLSKYGWLYIM-UHFFFAOYSA-N
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
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.
- 4-trimethylsilyl-1H-1,2,3-triazole-5-carbaldehyde by reacting with trimethylsilyl azide.
- 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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
84.9 °F
flash_point_c
29.4 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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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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