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.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)

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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.CS1 maint: uses authors parameter (link)

[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.CS1 maint: uses authors parameter (link)

[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.CS1 maint: uses authors parameter (link)