153583
1-(Trimethylsilyl)imidazole
96%
Synonym(s):
N-Trimethylsilylimidazole, TMSI, TSIM
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About This Item
Empirical Formula (Hill Notation):
C6H12N2Si
CAS Number:
Molecular Weight:
140.26
Beilstein:
606148
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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grade
synthesis grade
Quality Level
Assay
96%
form
liquid
refractive index
n20/D 1.475 (lit.)
bp
93-94 °C/14 mmHg (lit.)
density
0.956 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C[Si](C)(C)n1ccnc1
InChI
1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3
InChI key
YKFRUJSEPGHZFJ-UHFFFAOYSA-N
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Application
1-(Trimethylsilyl)imidazole (TMSI) was used for derivatization of carbohydrates into trimethylsilyl ethers. It was also used to synthesize polysubstituted chiral spirotetrahydropyrans and as silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.
Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.
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Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
42.8 °F - closed cup
Flash Point(C)
6 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Maiwenn Jacolot et al.
Organic letters, 14(1), 58-61 (2011-12-02)
We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
Synthetic Communications, 23, 2191-2191 (1993)
Marijana M Ačanski et al.
Food chemistry, 145, 743-748 (2013-10-17)
Gas chromatography with mass spectrometry was used for carrying out a qualitative analysis of the ethanol soluble flour extract of different types of cereals bread wheat and spelt and pseudocereals (amaranth and buckwheat). TMSI (trimethylsilylimidazole) was used as a reagent
Silylated N,O-ketals from the reaction of ketones with N-trimethylsilylimidazole.
P A Andrews et al.
Journal of chromatography, 419, 271-274 (1987-08-07)
S Kulkarni et al.
Steroids, 53(1-2), 131-147 (1989-01-01)
The reaction of trimethylsilylimidazole (TSIM) and 3-keto-5,10-epoxy-nor-19-methylandrostanone 3 and its 17-acetate analog 4 was examined at two different temperatures. In both compounds, reaction at 90 degrees C gave predominantly a delta 3-silyl-enol ether plus a minor product as a result
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