745537
4-(Acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate
97% (HPLC)
Synonym(s):
4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate, Bobbitt′s Salt
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About This Item
Empirical Formula (Hill Notation):
C11H21BF4N2O2
CAS Number:
Molecular Weight:
300.10
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Assay:
97% (HPLC)
Form:
solid
Quality Level
assay
97% (HPLC)
form
solid
reaction suitability
reagent type: oxidant
mp
191-197 °C (decomposition)
functional group
amide
storage temp.
2-8°C
SMILES string
F[B-](F)(F)F.CC(=O)NC1CC(C)(C)[N+](=O)C(C)(C)C1
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
General description
Bobbitt′s salt (oxoammonium salt) is a commonly used oxidizing agent in organic synthesis for the preparation of useful chemical intermediates. This reagent is highly stable to both air and moisture.
Application
Bobbitt′s salt (4-NHAc-TEMPO+ BF4 −) can be used as a reagent in:
- Oxidation of alcohols to their concomitant aldehyde, ketone or carboxylic acid.
- Conversion of aldehydes to hexafluoroisopropyl (HFIP) esters via oxidative esterification.,·
- Deprotection of allyl ethers to corresponding aldehydes.
- Preparation of α,β-unsaturated ketones by dehydrogenation of perfluoroalkyl ketones.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Related Content
Journal
Tilley, L. J.;
Synthesis, 3, 326-326 (2013)
Christopher B Kelly et al.
Organic letters, 15(9), 2222-2225 (2013-04-26)
A simple, high yielding, rapid route for the oxidative esterification of a wide range aldehydes to hexafluoroisopropyl (HFIP) esters using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1a) is reported. These esters can be readily transformed into a variety of other functional
Christopher B Kelly et al.
Organic & biomolecular chemistry, 13(14), 4255-4259 (2015-03-10)
A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 745537-25G | 04061833399859 |
| 745537-5G | 04061833339480 |