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N-Hydroxypiperidine

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N-Hydroxypiperidine
Names
Preferred IUPAC name Piperidin-1-ol
Other names 1-Hydroxypiperidine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 102726
ChemSpider
ECHA InfoCard 100.023.057 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H11NO/c7-6-4-2-1-3-5-6/h7H,1-5H2
SMILES
  • ON1CCCCC1
Properties
Chemical formula C5H11NO
Molar mass 101.149 g·mol
Appearance Fine white crystals
Density 1.070 g/cm
Melting point 39.3 °C (102.7 °F; 312.4 K)
Boiling point 98.5 °C (209.3 °F; 371.6 K)
Solubility in water 113 g/L
log P -0.17
Vapor pressure 0.542 Torr
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0 2 0
Flash point 84.9 °C (184.8 °F; 358.0 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

N-Hydroxypiperidine (also known as 1-piperidinol and 1-hydroxypiperidine) is the chemical compound with formula C5H11NO. It is a hydroxylated derivative of the heterocyclic compound piperidine.

Preparation

N-Hydroxypiperidine can be prepared from the application of meta-chloroperoxybenzoic acid and methanol to the tertiary amine product of acrylonitrile and piperidine, followed by heating with acetone of the resulting tertiary N-oxide.

Reactions

N-Hydroxypiperidine is a secondary amine, which can undergo an oxidation reaction with hydrogen peroxide in methanol as the solvent. This produces a nitrone, which is heteroatomic equivalent to a ketone with a nitrogen instead of an alpha carbon. Competing elimination reactions can occur, as well.

References

  1. O’Neil, I. A.; Cleator, E.; Tapolczay, D. J. A convenient synthesis of secondary hydroxylamines. Tetrahedron Letters, 2001, 42, pp. 8247–8249
  2. Zauche, Timothy H.; Espenson, James H. (1997). "Kinetics and Mechanism of the Oxidation of Secondary Hydroxylamines to Nitrones with Hydrogen Peroxide, Catalyzed by Methylrhenium Trioxide". Inorganic Chemistry. 36 (23): 5257. doi:10.1021/ic970649d.
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