2,6-Diisopropylaniline

2,6-Diisopropylaniline
Names
	Preferred IUPAC name 2,6-Di(propan-2-yl)aniline
	Other names 2,6-Diisopropylaniline; 2,6-DIPA
Identifiers
CAS Number	24544-04-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3183764;
ChemSpider	13859730;
ECHA InfoCard	100.042.081
EC Number	246-305-4;
PubChem CID	32484;
UNII	190BG0089I;
CompTox Dashboard (EPA)	DTXSID5022279 ;
	InChI InChI=1S/C12H19N/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9H,13H2,1-4H3 Key: WKBALTUBRZPIPZ-UHFFFAOYSA-N;
	SMILES CC(C)C1=C(C(=CC=C1)C(C)C)N;
Properties
Chemical formula	C12H19N
Molar mass	177.291 g·mol−1
Appearance	colorless liquid
Melting point	−45 °C (−49 °F; 228 K)
Boiling point	257 °C (495 °F; 530 K)
Hazards
GHS hazard statements	H412
GHS precautionary statements	P273, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2,6-Diisopropylaniline is an organic compound with the formula H₂NC₆H₃(CHMe₂)₂ (Me = CH₃). It is a colorless liquid although, like many anilines, samples can appear yellow or brown. 2,6-Diisopropylaniline is a bulky aromatic amine that is often used to make ligands in coordination chemistry. The Schrock carbenes often are transition metal imido complexes derived from this aniline.[1] Condensation with diacetylpyridine and acetylacetone gives, respectively, diiminopyridine[2] and NacNac ligands.[3]

Typical Schrock-style olefin metathesis catalysts feature bulky imides as spectator ligands.

Structure of the diamido-diimido complex W(NAr)₂(N(H)Ar)₂ (ArNH₂ = 2,6-Diisopropylaniline.[4]

References

R. R. Schrock (2009). "Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry". Chemical Reviews. 109: 3211–3226. doi:10.1021/cr800502p. PMC 2726908.
V. C. Gibson; M. J. Humphries; K. P. Tellmann; D. F. Wass; A. J. P. White; D. J. Williams (2001). "The nature of the active species in bis(imino)pyridyl cobalt ethylene polymerisation catalysts". Chem. Commun. doi:10.1039/b107490c. 2252.
Mindiola, D. J.; Holland, P. L.; Warren, T. H. (2010). "Complexes of Bulky β-Diketiminate Ligands". Inorg. Synth. 35: 1–55. doi:10.1002/9780470651568.ch1.
Tianniu Chen; K.R. Sorasaenee; Zhongzhi Wu; J. B. Diminnie; Ziling Xue (2003). "Synthesis, Characterization and X-ray Structures of New Molybdenum Bis(imide) Amide and Silyl Complexes". Inorg. Chim. Acta. 345: 113. doi:10.1016/S0020-1693(02)01271-9.

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[RRS-1] R. R. Schrock (2009). "Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry". Chemical Reviews. 109: 3211–3226. doi:10.1021/cr800502p. PMC 2726908.

[2] V. C. Gibson; M. J. Humphries; K. P. Tellmann; D. F. Wass; A. J. P. White; D. J. Williams (2001). "The nature of the active species in bis(imino)pyridyl cobalt ethylene polymerisation catalysts". Chem. Commun. doi:10.1039/b107490c. 2252.

[3] Mindiola, D. J.; Holland, P. L.; Warren, T. H. (2010). "Complexes of Bulky β-Diketiminate Ligands". Inorg. Synth. 35: 1–55. doi:10.1002/9780470651568.ch1.

[4] Tianniu Chen; K.R. Sorasaenee; Zhongzhi Wu; J. B. Diminnie; Ziling Xue (2003). "Synthesis, Characterization and X-ray Structures of New Molybdenum Bis(imide) Amide and Silyl Complexes". Inorg. Chim. Acta. 345: 113. doi:10.1016/S0020-1693(02)01271-9.