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4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate

Catalog Number
ACM219543096-1
Product Name
4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate
Structure
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CAS
219543-09-6
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Synonyms
RTR-010298; 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidin-1-ium tetrafluoroborate; AK543047; DTXSID90372980; 4-(Acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate 97%; AC1MBN1V; ANW-24638;
IUPAC Name
N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide;tetrafluoroborate;
Molecular Weight
300.105g/mol
Molecular Formula
C11H21BF4N2O2;
Canonical SMILES
[B-](F)(F)(F)F.CC(=O)NC1CC([N+](=O)C(C1)(C)C)(C)C;
InChI
InChI=1S/C11H20N2O2.BF4/c1-8(14)12-9-6-10(2,3)13(15)11(4,5)7-9;2-1(3,4)5/h9H,6-7H2,1-5H3;/q;-1/p+1;
InChI Key
HTMHEICBCHCWAU-UHFFFAOYSA-O;
Storage
2-8°C
Complexity
294
Covalently-Bonded Unit Count
2
Exact Mass
300.163g/mol
H-Bond Acceptor
7
H-Bond Donor
1
Heavy Atom Count
20
Monoisotopic Mass
300.163g/mol
Rotatable Bond Count
1
Topological Polar Surface Area
49.2A^2
Application
4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate serves as a versatile reagent in organic synthesis, widely appreciated for its role as a stable oxidizing agent. Its primary purpose includes the oxidation of alcohols into corresponding aldehydes, ketones, or carboxylic acids, thus facilitating a range of transformations. Additionally, it enables the conversion of aldehydes into hexafluoroisopropyl (HFIP) esters through oxidative esterification and aids in the deprotection of allyl ethers to yield aldehydes. Furthermore, it is instrumental in the preparation of α,β-unsaturated ketones by facilitating the dehydrogenation of perfluoroalkyl ketones. Its stability against air and moisture enhances its utility in producing valuable chemical intermediates.
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