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

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.

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.345
EC Number
  • 253-197-2
UNII
  • InChI=1S/C9H20N2/c1-8(2)5-7(10)6-9(3,4)11-8/h7,11H,5-6,10H2,1-4H3
    Key: FTVFPPFZRRKJIH-UHFFFAOYSA-N
  • CC1(CC(CC(N1)(C)C)N)C
Properties
C9H20N2
Molar mass 156.273 g·mol−1
Appearance colorless liquid
Density 0.8966 g/cm3
Melting point 17 °C (63 °F; 290 K)
Boiling point 188.5 °C (371.3 °F; 461.6 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H290, H302, H314, H412
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 [77 °F], 100 kPa).
Infobox references

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:[1]

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

Compound Properties

Boiling point is 188.5 °C [2] Melting point is 17 °C. [3] Density is 0.8966 g/cm3 @ Temp: 20 °C [4]

Toxicity

A study by Truda et al, has reported the median lethal dose LD(50) as 906mg/kg in rats. .[5]

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. [PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4]
  3. [PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4]
  4. [PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4]
  5. [ Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(5), Pg. 53, 1984]

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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