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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
Empirical Formula (Hill Notation):
C11H21BF4N2O2
CAS Number:
Molecular Weight:
300.10
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Related Categories

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.

Packaging

5, 25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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