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

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	36768-62-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL368366;
ChemSpider	34423;
ECHA InfoCard	100.048.345
EC Number	253-197-2;
PubChem CID	37524;
UNII	ETF220Q65R;
CompTox Dashboard (EPA)	DTXSID3044388 ;
	InChI 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;
	SMILES CC1(CC(CC(N1)(C)C)N)C;
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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 (LD₅₀) as 906 mg/kg in rats.

Related compounds

References

↑ 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.
1 2 3 [PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4]
↑ [ Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(5), Pg. 53, 1984]

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.

[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.

[commonchemistry-2] 1 2 3 [PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4]

[3] [ Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(5), Pg. 53, 1984]

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

Compound Properties

Toxicity

Related compounds

References

Further reading