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745537

Sigma-Aldrich

4-(Acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate

97% (HPLC)

Sinônimo(s):

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate, Bobbitt′s Salt

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About This Item

Fórmula empírica (Notação de Hill):
C11H21BF4N2O2
Número CAS:
219543-09-6
Peso molecular:
300.10
Número MDL:
MFCD29060212
Código UNSPSC:
12352005
ID de substância PubChem:
329764990
NACRES:
NA.22

R$ 219,00

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Nível de qualidade

100

Ensaio

97% (HPLC)

Formulário

solid

adequação da reação

reagent type: oxidant

pf

191-197 °C (decomposition)

grupo funcional

amide

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

HTMHEICBCHCWAU-UHFFFAOYSA-O

Categorias relacionadas

Descrição geral

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.[1][2]

Aplicação

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.[1][2]      
  • Conversion of aldehydes to hexafluoroisopropyl (HFIP) esters via oxidative esterification.[2],·        
  • Deprotection of allyl ethers to corresponding aldehydes.[3]
  •  Preparation of α,β-unsaturated ketones by dehydrogenation of perfluoroalkyl ketones.[4]

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
WXBF5367V
WXBF2786V
WXBD9436V
MKCS0047
MKCM1851

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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.
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
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

Conteúdo relacionado

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.

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