Accéder au contenu
Merck
Toutes les photos(2)

Key Documents

View All Documentation

745537

Sigma-Aldrich

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

97% (HPLC)

Synonyme(s) :

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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(2)

About This Item

Formule empirique (notation de Hill):
C11H21BF4N2O2
Numéro CAS:
219543-09-6
Poids moléculaire :
300.10
Code UNSPSC :
12352005
ID de substance PubChem :
329764990
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97% (HPLC)

Forme

solid

Pertinence de la réaction

reagent type: oxidant

Pf

191-197 °C (decomposition)

Groupe fonctionnel

amide

Température de stockage

2-8°C

Chaîne 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

Clé InChI

HTMHEICBCHCWAU-UHFFFAOYSA-O

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCM1851
MKCF0035
MKBW9079V
MKBT5819V
MKBP7209V

Vous ne trouvez pas la bonne version ?

Si vous avez besoin d'une version particulière, vous pouvez rechercher un certificat spécifique par le numéro de lot.

Rechercher un(e) COA

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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.
Dehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt
Hamlin TA, et al.
European Journal of Organic Chemistry, 2013(18), 3658-3661 (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

Contenu apparenté

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.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique