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4-Amino-2,2,6,6-tetramethylpiperidine

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4-Amino-2,2,6,6-tetramethylpiperidine
Names
Preferred IUPAC name 2,2,6,6-Tetramethylpiperidin-4-amine
Other names 2,2,6,6-Tetramethyl-4-aminopiperidine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.345 Edit this at Wikidata
EC Number
  • 253-197-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H20N2/c1-8(2)5-7(10)6-9(3,4)11-8/h7,11H,5-6,10H2,1-4H3Key: FTVFPPFZRRKJIH-UHFFFAOYSA-N
SMILES
  • CC1(CC(CC(N1)(C)C)N)C
Properties
Chemical formula C9H20N2
Molar mass 156.273 g·mol
Appearance colorless liquid
Density 0.8966 g/cm
Melting point 17 °C (63 °F; 290 K)
Boiling point 188.5 °C (371.3 °F; 461.6 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H290, H302, H314, H412
Precautionary statements P234, P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P390, P404, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

4-Amino-2,2,6,6-tetramethyl-4-piperidine is an organic compound with the formula H2NCH(CH2CMe2)2NH (where Me = CH3). Classified as a diamine, it is a colorless oily liquid.

The compound is an intermediate in the preparation of Bobbitt's salt, an oxidant used in organic synthesis. It is prepared by the reductive amination of the corresponding ketone:

OC(CH2CMe2)2NH + NH3 + H2 → H2NCH(CH2CMe2)2NH + H2O

Compound Properties

Boiling point is 188.5 °C Melting point is 17 °C. Density is 0.8966 g/cm3 @ Temp: 20 °C

Toxicity

A study by Truda et al, has reported the median lethal dose LD(50) as 906mg/kg in rats. .

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.

Related compounds

Further reading

  • C. McFarland; D. Vicic; A. Debnath (2006). "Rapid Microwave-Assisted Syntheses of Derivatives of HIV-1 Entry Inhibitors". Synthesis. 2006 (5): 807–812. doi:10.1055/s-2006-926339.
  • L. Tilley; J. Bobbitt; S. Murray; C. Camire (2013). "A Revised Preparation of (4-Acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate: Reagents for Stoichiometric Oxidations of Alcohols". Synthesis. 45 (3): 326–329. doi:10.1055/s-0032-1317861.
  • A. Germanova; L. Aizvert; A. Shidlovskaia; L. Melnikova; M. Bidevkina (1984). "Comparative characteristics of the toxicity, safety and nature of the biological effect on the body of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 4-amino-2,2,6,6-tetramethylpiperidine". Gig Tr Prof Zabol (5): 53–54. PMID 6745687.
  • M. Gergely; A. Takacs; L.Kollar (2016). "4-Amino-TEMPO as N-Nucleophile in Palladium-Catalyzed Aminocarbonylation". Heterocyclic Chemistry. 54 (1): 634–640. doi:10.1002/jhet.2635.
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