174677-82-8

Basic information

• Product Name: (S,S)-1,2-Bis{{[2-(diphenylphosphino)phenyl]methylene}amino}cyclohexane
• Synonyms: (S,S)-1,2-Bis{{[2-(diphenylphosphino)phenyl]methylene}amino}cyclohexane;(S,S)-N,Nμ-Bis[2-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine;(S,S)-N,Nμ-Bis[o-(diphenylphosphino)benzylidene]-1,2-diaminocyclohexane
• CAS NO: 174677-82-8
• Molecular Formula: C44H40N2P2
• Molecular Weight: 658.749322
• Product Categories: Building Blocks;Chemical Synthesis;Imines/Amidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 174677-82-8.mol

Chemical Properties

• Appearance: /
• BRN: 16417971
• CAS DataBase Reference: (S,S)-1,2-Bis{{[2-(diphenylphosphino)phenyl]methylene}amino}cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-1,2-Bis{{[2-(diphenylphosphino)phenyl]methylene}amino}cyclohexane(174677-82-8)
• EPA Substance Registry System: (S,S)-1,2-Bis{{[2-(diphenylphosphino)phenyl]methylene}amino}cyclohexane(174677-82-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 174677-82-8(Hazardous Substances Data)

Upstream product

• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 50777-76-9 (2-formylphenyl)(diphenyl)phosphine 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 829-85-6 diphenylphosphane 
• 6630-33-7 ortho-bromobenzaldehyde 

Relevant articles and documents

The formation of hemiacetal complexes of rhenium(V) by degradation of a Schiff base

Mono- and dinuclear oxidorhenium(V) complexes with hemiacetal ligands were isolated from a reaction of (NBu4)[ReOCl4] with a potentially tetradentate Schiff base prepared from (1R,2R)-cyclohexane-1, 2-diamine and (2-formylphenyl)diphenylphosphine in methanol. The hemiacetal is formed by solvolysis of first one imine functionality of the Schiff base, whereas the second remains intact. The resulting amine/iminophosphine coordinates as a tridentate N,N, P ligand in a dinuclear compound. Ongoing degradation of the Schiff base gives more hemiacetal (HL1a) and the final product, the monomeric complex [ReOCl(L1a)2] is formed. Cleavage of the organic framework is not observed during the reaction of (NBu4)[ReOCl4] with a related Schiff base derived from ethylene-1, 2-diamine and (2-formylphenyl)diphenylphosphine. The Schiff base reacts as a bis-bidentate N, P ligand and a dinuclear oxorhenium(V) compound with a central ethylene bridge is formed. Copyright

Asymmetric synthesis of cyclic ethers by rearrangement of oxonium ylides generated from chiral copper carbenoids

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Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands

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Process for hydrogenation of carbonyl and iminocarbonyl compounds using ruthenium catalysts comprising tetradentate diimino-diphosphine ligands

A process for the hydrogenation, using molecular hydrogen (H2), of a catalytic system, wherein the catalytic system comprises a base and a complex of formula; (II) wherein Y represents simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and N2P2 is a tetradentate diimine-diphosphino ligand.

Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone

The application of homogeneously soluble catalysts is limited by the recovery in cases where the price of the catalyst is high. Biological catalysts, enzymes, can be efficiently recycled by means of an ultrafiltration membrane due to their high molecular weight, for example, in the continuously operated membrane reactor. In order to transfer this principle to chemical catalysis, we have attached a transfer hydrogenation catalyst, first invented by Gao and Noyori, to a polymer. The resulting homogeneously soluble, polymer-bound catalyst (chemzyme) can now be retained by ultrafiltration membranes like enzymes. On applying this catalyst in continuously operated membrane reactors, a continuous isopropoxide dosage is necessary in order to compensate deactivation caused by water residues in the feed stream. Thus, high space-time yields up to 578 g L-1 d-1 and enantioselectivities up to 94% can he achieved. These results were compared to an enzyme catalyzed system consisting of a carbonyl reductase that also utilizes 2-propanol as a hydrogen source for the cofactor regeneration of NADH.

New chiral cationic rhodium-aminophosphine complexes for asymmetric transfer hydrogenation of aromatic ketones

The new chiral ligands (S,S)-N,N′-bis[o-(diphenylphosphino)benzylidene]1,2-diiminocyclohexane, [(S,S)-1] and (S,S)-N,N′-bis[o-diphenylphosphino]benzyl-1,2-diaminocyclohexane, [(S,S)-2] have been prepared. The interaction of [(S,S)-1] and [(S,S)-2] with [Rh(COD)Cl]2 afforded the corresponding cationic rhodium complexes [(S,S)-3][X] and [(S,S)-4][X] (X=PF6-, BF4- or ClO4-), respectively. [(S,S)-1], [(S,S)-2], [(S,S)-3][X] and [(S,S)-4][X] have been fully characterized by elemental analyses and spectroscopic methods. These chiral cationic rhodium complexes serve as catalytst precursors for the asymmetric transfer hydrogenation of acetophenone derivatives in 2-propanol and [(S,S)-4][PF6] acts as an excellent catalyst in the reduction of m-chloroacetophenone, giving the corresponding optical alcohols in 99% yield and up to 94% ee.