Bobbitt's salt
Names
IUPAC name
N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide;tetrafluoroborate
Other names
4-(Acetylamino)-2,2,6,6-tetramethyl-1-oxo-piperidinium tetrafluoroborate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.202.272
  • 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
    Key: HTMHEICBCHCWAU-UHFFFAOYSA-O
  • [B-](F)(F)(F)F.CC(=O)NC1CC([N+](=O)C(C1)(C)C)(C)C
Properties
C11H21BF4N2O2
Molar mass 300.10 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bobbitt's salt is an oxoammonium compound derived from 4-acetamido-2,2,6,6-tetramethylpiperidine. It contains the tetrafluoroborate anion and is named after the American chemist James M. Bobbitt.

As a less expensive analogue of the N-oxoammonium salt derived from TEMPO, Bobbitt's salt is still mainly used as a catalyst for oxoammonium-catalyzed oxidations.[1][2]

References

  1. ↑ Nabyl Merbouh; James M. Bobbitt; Christian Brückner (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International. 36: 1-31. doi:10.1080/00304940409355369. S2CID 98117103.
  2. ↑ James M.Bobbitt; Nicholas A.Eddy; Jay J.Richardson; Stephanie A.Murray; Leon J.Tilley (2013). "Discussion Addendum for: Preparation of 4-Acetylamino-2, 2, 6, 6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate and the Oxidation of Geraniol to Geranial (2,6-Octadienal, 3,7-dimethyl-, (2e)-)". Org. Synth. 90: 215. doi:10.15227/orgsyn.090.0215.
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