2,6-diisopropylaniline

Structural formula
General
Surname	2,6-diisopropylaniline
other names	2,6-bis (1-methylethyl) benzenamine ( system. IUPAC ); 2,6-diisopropylphenylamine;
Molecular formula	C 12 H 19 N
Brief description	yellowish odorless liquid
External identifiers / databases
EC number	246-305-4
ECHA InfoCard	100,042,081
PubChem	32484
ChemSpider	13859730
Wikidata	Q27252049
properties
Molar mass	177.29 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−45 ° C
boiling point	257 ° C
Vapor pressure	<0.01 hPa
solubility	<0.2 g / l in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: 412
	P: 273
Toxicological data	3200 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Diisopropylaniline is a liquid aromatic amine with the formula H ₂ NC ₆ H ₃ (CH (CH ₃ ) ₂ ) ₂ . It is a colorless liquid, but like many other aniline derivatives , samples can appear yellow or brown.

use

Due to its high steric demand , 2,6-diisopropylaniline is used for the synthesis of ligands in coordination chemistry . Many transition metal complexes based on Schrock carbene carry imido ligands derived from this aniline. The condensation with 2,6-diacetylpyridine leads to diiminopyridine ligands , that with acetylacetone to NacNac ligands .

In some carbenes, too, the sterically demanding diisopropylphenyl substituents are introduced by 2,6-diisopropylaniline.

A typical Schrock-type catalyst in olefin metathesis that carries a sterically demanding imine based on 2,6-diisopropylaniline as an observer ligand.
Structure of the diamido diimido complex W (NAr) ₂ (N (H) Ar) ₂ (ArNH ₂ = 2,6-diisopropylaniline).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,6-diisopropylaniline in the GESTIS substance database of the IFA , accessed on November 10, 2019 (JavaScript required)
↑ Richard R. Schrock : Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry . In: Chemical Reviews . tape 109 , no. 8 , August 12, 2009, p. 3211-3226 , doi : 10.1021 / cr800502p , PMID 19284732 , PMC 2726908 (free full text).
↑ Vernon C. Gibson, Martin J. Humphries, Kilian P. Tellmann, Duncan F. Wass, Andrew JP White: [No title found] . In: Chemical Communications . No. 21 , October 23, 2001, p. 2252-2253 , doi : 10.1039 / b107490c .
↑ Complexes of Bulky β-Diketiminate Ligands . In: Inorganic Syntheses . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-65156-8 , pp. 1-55 , doi : 10.1002 / 9780470651568.ch1 .
↑ Vincent Lavallo, Yves Canac, Carsten Presang, Bruno Donnadieu, Guy Bertrand: Stable Cyclic (Alkyl) (Amino) Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference . In: Angewandte Chemie International Edition . tape 44 , no. 35 , September 5, 2005, pp. 5705-5709 , doi : 10.1002 / anie.200501841 .
^ Matthew Asay, Bruno Donnadieu, Antoine Baceiredo, Michele Soleilhavoup, Guy Bertrand : Cyclic (Amino) [bis (ylide)] carbene as an Anionic Bidentate Ligand for Transition-Metal Complexes . In: Inorganic Chemistry . tape 47 , no. 10 , May 2008, p. 3949-3951 , doi : 10.1021 / ic800459p , PMID 18422308 , PMC 2574712 (free full text).
↑ Tianniu Chen, Karn R Sorasaenee, Zhongzhi Wu, Jonathan B Diminnie, Ziling Xue: Synthesis, characterization and X-ray structures of new molybdenum bis (imide) amide and silyl complexes . In: Inorganica Chimica Acta . tape 345 , March 2003, p. 113-120 , doi : 10.1016 / S0020-1693 (02) 01271-9 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,6-diisopropylaniline in the GESTIS substance database of the IFA , accessed on November 10, 2019 (JavaScript required)

[2] Richard R. Schrock : Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry . In: Chemical Reviews . tape 109 , no. 8 , August 12, 2009, p. 3211-3226 , doi : 10.1021 / cr800502p , PMID 19284732 , PMC 2726908 (free full text).

[3] Vernon C. Gibson, Martin J. Humphries, Kilian P. Tellmann, Duncan F. Wass, Andrew JP White: [No title found] . In: Chemical Communications . No. 21 , October 23, 2001, p. 2252-2253 , doi : 10.1039 / b107490c .

[4] Complexes of Bulky β-Diketiminate Ligands . In: Inorganic Syntheses . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-65156-8 , pp. 1-55 , doi : 10.1002 / 9780470651568.ch1 .

[5] Vincent Lavallo, Yves Canac, Carsten Presang, Bruno Donnadieu, Guy Bertrand: Stable Cyclic (Alkyl) (Amino) Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference . In: Angewandte Chemie International Edition . tape 44 , no. 35 , September 5, 2005, pp. 5705-5709 , doi : 10.1002 / anie.200501841 .

[6] Matthew Asay, Bruno Donnadieu, Antoine Baceiredo, Michele Soleilhavoup, Guy Bertrand : Cyclic (Amino) [bis (ylide)] carbene as an Anionic Bidentate Ligand for Transition-Metal Complexes . In: Inorganic Chemistry . tape 47 , no. 10 , May 2008, p. 3949-3951 , doi : 10.1021 / ic800459p , PMID 18422308 , PMC 2574712 (free full text).

[7] Tianniu Chen, Karn R Sorasaenee, Zhongzhi Wu, Jonathan B Diminnie, Ziling Xue: Synthesis, characterization and X-ray structures of new molybdenum bis (imide) amide and silyl complexes . In: Inorganica Chimica Acta . tape 345 , March 2003, p. 113-120 , doi : 10.1016 / S0020-1693 (02) 01271-9 .