CAS 74663-75-5 (1E,2E)-1,2-Bis(2,6-Diisopropylphenylimino)ethane

Synonyms

N,N'-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene; N,N'-Bis(2,6-diisopropylphenyl)ethanediimine; Glyoxal bis(2,6-diisopropylanil)

IUPAC Name

N,N'-bis[2,6-di(propan-2-yl)phenyl]ethane-1,2-diimine;

Molecular Weight

376.58

Molecular Formula

C₂₆H₃₆N₂

Canonical SMILES

CC(C)C1=C(C(=CC=C1)C(C)C)N=CC=NC2=C(C=CC=C2C(C)C)C(C)C;

InChI

InChI=1S/C26H36N2/c1-17(2)21-11-9-12-22(18(3)4)25(21)27-15-16-28-26-23(19(5)6)13-10-14-24(26)20(7)8/h9-20H,1-8H3;

InChI Key

JWVIIGXMTONOFR-UHFFFAOYSA-N;

Melting Point

105-109° C

Storage

room temperature

Complexity

425

Covalently-Bonded Unit Count

Exact Mass

376.288g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

376.288g/mol

Rotatable Bond Count

Topological Polar Surface Area

24.7A^2

Application

The compound (1E,2E)-1,2-Bis(2,6-Diisopropylphenylimino)ethane serves multiple significant purposes in advanced chemical processes. It is primarily utilized as a reactant in the synthesis of ruthenium-based olefin metathesis catalysts, essential for facilitating various chemical transformations. Additionally, it functions as an N-cyclic carbene ligand and acts as a catalyst in palladium-catalyzed aerobic alcohol oxidation, which is enhanced by α-diimine ligands. The compound is instrumental in regioselective alkylation processes when used in conjunction with ruthenium-bisimine catalytic precursors, and it supports N-arylation of aromatic amines. Furthermore, it is involved in the preparation of ruthenium nitrosyl alpha-diimine and iminoketone complexes, which are vital catalysts for the transfer hydrogenation of ketones and atom transfer radical polymerization reactions.

February 28, 2025

Exceptional Catalyst Performance!

I used Alfa Chemistry's (1E,2E)-1,2-Bis(2,6-Diisopropylphenylimino)ethane in synthesizing ruthenium olefin metathesis catalysts. Superior efficiency and precision in regioselective alkylation and N-arylation enhanced our research outcomes significantly.