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2,6-Diisopropylaniline

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]

2,6-Diisopropylaniline
Names
Preferred IUPAC name
2,6-Di(propan-2-yl)aniline
Other names
2,6-Diisopropylaniline
2,6-DIPA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.042.081 Edit this at Wikidata
EC Number
  • 246-305-4
UNII
  • 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
  • CC(C)C1=C(C(=CC=C1)C(C)C)N
Properties
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 labelling:
H412
P273, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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

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  1. ^ R. R. Schrock (2009). "Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry". Chemical Reviews. 109 (8): 3211–3226. doi:10.1021/cr800502p. PMC 2726908. PMID 19284732.
  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. (21): 2252–2253. doi:10.1039/b107490c. PMID 12240136. 2252.
  3. ^ Mindiola, D. J.; Holland, P. L.; Warren, T. H. (2010). "Complexes of Bulky β-Diketiminate Ligands. In Inorg. Synth.". Inorganic Syntheses. Vol. 35. pp. 1–55. doi:10.1002/9780470651568.ch1. ISBN 9780471682554.
  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.
 

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