Wikipedia

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 Edit this at Wikidata
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).

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

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

Toxicity

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

References

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  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]
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Further reading

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  • 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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