2,2,6,6-Tetramethylpiperidine
2,2,6,6-Tetramethylpiperidine
Names
Preferred IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine Tetramethylpiperidine
Identifiers
Abbreviations
TMP
ChEMBL
ChemSpider
ECHA InfoCard
100.011.090
EC Number
UNII
InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
Y Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N
Y InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
Key: RKMGAJGJIURJSJ-UHFFFAOYAX
Properties
C 9 H 19 N
Molar mass
141.254 g/mol
Appearance
Clear liquid
Density
0.83 g/mL
Melting point
−59 °C (−74 °F; 214 K)
Boiling point
152 °C (306 °F; 425 K)
Hazards
GHS labelling :
Danger
H226 , H301 , H302 , H314 , H315 , H319 , H332 , H335
P210 , P233 , P240 , P241 , P242 , P243 , P260 , P261 , P264 , P270 , P271 , P280 , P301+P310 , P301+P312 , P301+P330+P331 , P302+P352 , P303+P361+P353 , P304+P312 , P304+P340 , P305+P351+P338 , P310 , P312 , P321 , P330 , P332+P313 , P337+P313 , P362 , P363 , P370+P378 , P403+P233 , P403+P235 , P405 , P501
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
2,2,6,6-Tetramethylpiperidine , abbreviated TMP , HTMP , or TMPH , is an organic compound of the amine class. In appearance, it is a colorless liquid and has a "fishy", amine-like odor. This amine is used in chemistry as a hindered base (hindered amine ). Although TMP finds limited use per se, its derivatives are a mainstay of hindered amine light stabilizers .
TMP is the starting material for an even stronger base, lithium tetramethylpiperidide and the radical species TEMPO . Another non-nucleophilic base is N,N-diisopropylethylamine . Its aqueous pK aH (conjugate acid dissociation constant, a measure of basicity) is 11.07 at 25 °C,[ 1] while its pK a (acid dissociation constant, a measure of acidity) is approximately 37.[ 2]
Preparation
Many routes for the synthesis of TMP have been reported. One method[ 3] starts with a conjugate addition reaction of ammonia to phorone . The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction .
TMP synthesis
See also
References
^ William M. Haynes, ed. (2015). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data (96th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4822-6096-0 . OCLC 910908643 .
^ Reich, Hans (2022). "Bordwell pKa table" .
^ Detlef Kampmann; Georg Stuhlmüller; Roger Simon; Fabrice Cottet; Frédéric Leroux; Manfred Schlosser (2005). "A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor". Synthesis . 2005 (6): 1028–1029. doi :10.1055/s-2004-834856 . S2CID 93476763 .
External links