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Merck
CN
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文件

745537

Sigma-Aldrich

4-（乙酰氨基）-2,2,6,6-四甲基-1-氧代哌啶四氟硼酸

97% (HPLC)

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所有图片(2)
别名:
4-乙酰胺基-2,2,6,6-四甲基-1-氧代哌啶四氟硼酸盐, Bobbitt盐
经验公式（希尔记法）:
C11H21BF4N2O2
CAS号:
219543-09-6
分子量:
300.10
UNSPSC代码:
12352005
PubChem化学物质编号:
329764990
NACRES:
NA.22

质量水平

100

检测方案

97% (HPLC)

形式

solid

反应适用性

reagent type: oxidant

mp

191-197 °C (decomposition)

储存温度

2-8°C

SMILES字符串

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

相关类别

一般描述

Bobbitt盐是有机合成中常用的制备化学中间产物的氧化剂。该试剂对空气和湿度高度稳定。

应用

Bobbitt盐 (4-NHAc-TEMPO+ BF4 −) 可作为试剂用于：       
  • 将醇类氧化为其对应醛、酮或羧酸形式。      
  • 通过氧化酯化将醛类转化为六氟异丙基 (HFIP) 酯类,·        
  • 通过脱保护作用将烯丙基醚转化为相应的醛。
  • 通过全氟烷基酮的脱氧反应制备α,β-不饱和酮。

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315,H319,H335

危险分类

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

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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Tilley, L. J.;
Synthesis, 3, 326-326 (2013)
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)
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
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

相关内容

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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