Triisopropylamine

Triisopropylamine

Names
Preferred IUPAC name N,N-Di(propan-2-yl)propan-2-amine
Other names Tri(propan-2-yl)amine (Triisopropyl)amine
Identifiers
CAS Number	3424-21-3 Y
3D model (Jmol)	Interactive image
ChemSpider	55785 N
ECHA InfoCard	100.020.289
EC Number	222-317-5
PubChem	61924
UNII	Y67CF9Z56L Y
InChI InChI=1S/C9H21N/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3 N Key: RKBCYCFRFCNLTO-UHFFFAOYSA-N N
SMILES CC(C)N(C(C)C)C(C)C
Properties
Chemical formula	C9H21N
Molar mass	143.27 g·mol−1
Appearance	Colorless liquid
Odor	Ichtyal, ammoniacal
Density	0.752 g/cm3
Boiling point	47 °C (117 °F; 320 K) at 1.9 kPa
Related compounds
Related amines	Dimethylamine Trimethylamine N-Nitrosodimethylamine Diethylamine Triethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine N,N-Diisopropylethylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Related compounds	Unsymmetrical dimethylhydrazine Biguanide Dithiobiuret Agmatine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Triisopropylamine is an organic chemical compound consisting of three isopropyl groups bound to a central nitrogen atom. As a hindered tertiary amine, it can be used as a non-nucleophilic base and as a stabilizer for polymers; however, its applications are limited by its relatively high cost and difficult synthesis.

Triisopropylamine is notable as being the most sterically crowded amine currently known. The even more crowded tri-tert-butyl-amine (^tBu₃N) has never been successfully synthesized, although the existence of 2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol (^tBu₃COH) implies that it may be possible.

In the early 1990s, theoretical studies and electron diffraction analysis of the 3D structure of the molecule, in the gas phase or in non-polar solvents, indicated that the bonds between the nitrogen atom and the three carbon atoms were nearly coplanar in the ground state, instead of forming a trigonal pyramid as in simpler amines. The average C-N-C angle was claimed to be 119.2°, much closer to the 120° of the flat configuration than to the 111.8° of trimethylamine. This peculiarity was attributed to steric hindrance by the bulky isopropyl radicals. However, in 1998 X-ray diffraction analysis of the crystallized solid showed that the C₃N core is actually pyramidal, with the N atom lying approximately 0.28 Å off the carbons' plane (whereas in trimethylamine the distance is about 0.45 Å). However the researchers could not rule out the crystal field effect as the cause of the asymmetry.