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745537

Sigma-Aldrich

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:
219543-09-6
Molecular Weight:
300.10
UNSPSC Code:
12352005
PubChem Substance ID:
329764990
NACRES:
NA.22

Assay

97% (HPLC)

form

solid

reaction suitability

reagent type: oxidant

mp

191-197 °C (decomposition)

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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.
Dehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt
Hamlin TA, et al.
European Journal of Organic Chemistry, 2013(18), 3658-3661 (2013)
Tilley, L. J.;
Synthesis, 3, 326-326 (2013)
Michael A Mercadante et al.
Nature protocols, 8(4), 666-676 (2013-03-09)
We describe the synthesis of the lesser-known stoichiometric oxidation reagent 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1, Bobbitt's salt), as well as of 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (2, AcNH-TEMPO). Several representative oxidation reactions are also presented to demonstrate the salt's oxidative capabilities. Bobbitt's salt has a range

Related Content

Bobbitt Group – Professor Product Portal

Dr. James Bobbitt has been developing the chemistry of oxoammonium salts, such as Bobbitt's Salt (Product 745537), for 30 years. He discovered the oxoaommonium chemistry by accident in 1985 and found that it had been started by a fine Russian chemist called Valery Golubev. At the University of Connecticut, he has had major collaborations with Professor Christian Bruckner, Professor William Bailey, and Professor Nicholas Leadbeater. He does most of his own experimental work, much of which has been published. Even though he is into his mid-80's, he continues to work on several chemistry projects as an Emeritus Professor at UConn.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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