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Merck

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)

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

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About This Item

经验公式(希尔记法):
C11H21BF4N2O2
分子量:
300.10
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22

品質等級

化驗

97% (HPLC)

形狀

solid

反應適用性

reagent type: oxidant

mp

191-197 °C (decomposition)

官能基

amide

儲存溫度

2-8°C

SMILES 字串

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 密鑰

HTMHEICBCHCWAU-UHFFFAOYSA-O

一般說明

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。

應用

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。

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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访问文档库

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

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