135616-36-3

Basic information

• Product Name: (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE
• Synonyms: (1S,2S)-(+)-1,2-CYCLOHEXANEDIAMINO-N,N'-BIS(3,5-DI-T-BUTYLSALICYLIDENE);(S,S)-(+)-N,N'-BIS(3,5-DI-T-BUTYLSALICYL-IDENE)-1,2-CYCLOHEXANEDIAMINE;(S,S)-(-)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE;(S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE;(S,S)-JACOBSEN'S LIGAND;(S,S)-JACOBSEN LIGAND;(S,S)-(+)-N,N'-BIS(3,5-DI-T-BU-SALICYL.);(1S,2S)-(+)-1,2-Cyclohexanediamino-N,N'-bis(3,5-di-tert-butylsalicylidene)
• CAS NO: 135616-36-3
• Molecular Formula: C₃₆H₅₄N₂O₂
• Molecular Weight: 546.83
• Product Categories: Aromatics;Catalyst;Chelating Agents & Ligands;Intermediates
• Mol File: 135616-36-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 203-206 °C(lit.)
• Boiling Point: 619.74°C (rough estimate)
• Flash Point: 115.2°C
• Appearance: yellow/Powder
• Density: 1.0110 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.06±0.40(Predicted)
• BRN: 5464823
• CAS DataBase Reference: (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE(135616-36-3)
• EPA Substance Registry System: (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE(135616-36-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 135616-36-3(Hazardous Substances Data)

Usage

Reaction

A versatile ligand for asymmetric catalysis. (a) Conjugate addition of hydrazoic acid to unsaturated imides. (b) Formation of cyanohydrins from aldehydes. (c) Desymmetrization of meso-epoxides with azide. (d) Hetero Diels-Alder reaction. (e) Nozaki-Hiyama reaction. (f) Reagent used for the Passerini, three-component reaction.

Chemical Properties

(S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE is yellow powder

Uses

Different sources of media describe the Uses of 135616-36-3 differently. You can refer to the following data:
1. (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE is a versatile ligand used in the preparation of Jacobsen's catalyst.
2. (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is a chiral salen-type ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.

Upstream product

• 37942-07-7 3,5-di-tert-butyl-2-hydroxybenzaldehyde 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 32044-22-7 (1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate 

Downstream Products

• 188264-84-8 [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) 
• 357418-50-9 methyl (S)-(+)-4-methylcyclohex-1-ene-4-carboxylate 

Relevant articles and documents

Shedding light on the use of Cu(ii)-salen complexes in the A3 coupling reaction

One Cu(ii) complex, {Cu(ii)L} (1S), has been synthesised, in two high yielding steps under ambient conditions, and characterised by single-crystal X-Ray diffraction (SXRD), IR, UV-Vis, circular dichroism (CD), elemental analysis, thermogravimetric analysis (TGA) and electron spray ionization mass spectroscopy (ESI-MS). This air-stable compound enables the generation, at room temperature and in open-air, of twenty propargylamines, nine new, from secondary amines, aliphatic aldehydes and alkynes with a broad scope with yields up to 99%. Catalyst loadings can be as low as 1 mol%, while the recovered material retains its structural integrity and can be used up to 5 times without loss of its activity. Control experiments, SXRD, cyclic voltammetry and theoretical studies shed light on the mechanism revealing that the key to success is the use of phenoxido salen based ligands. These ligands orchestrate topological control permitting alkyne binding with concomitant activation of the C-H bond and simultaneously acting as a template temporarily accommodating the abstracted acetylenic proton, and continuously generating, via in situ formed radicals and a Single Electron Transfer (SET) mechanism, a transient Cu(i) active site to facilitate this transformation. The scope and limitations of this protocol are discussed and presented.

Catalytic asymmetric synthesis of O-acetylcyanohydrins from potassium cyanide, acetic anhydride, and aldehydes, promoted by chiral salen complexes of titanium(IV) and vanadium(V)

The utility of the chiral [Ti(μ-O)(salen)]2 complexes (R)- and (S)-1 (H2salen was prepared from (R,R)- or (S,S)-cyclohexane-1,2-diamine and 3.5-di(tert-butyl)-2-hydroxybenzaldehyde) as catalysts for the asymmetric addition of KCN and Ac2O to aldehydes to produce O-acetylcyanohydrins was investigated. It was shown that the complexes were active at a substrate/catalyst ratio of 100:1 and produced the O-protected cyanohydrins with ee in the range of 60-92% at -40°. Other complexes, [Ti2(AcO)2(μ-O)(salen)2] ((R)-4) and [Ti(CF3COO)2(salen)] ((R)-5), were prepared from (R)-1 by treatment with different amounts of Ac2O and (CF3CO)2O, and their catalytic activities were tested under the same conditions. The efficiency of (R)-4 was found to be even greater than that of (R)-1, whereas (R)-5 was inactive. The synthesis of the corresponding salen complexes of VIV and VV,[V(O)(salen)] ((R)-2) and [V(O)(salen)(H2O)][S(O)3OEt] ((R)-3), was elaborated. and their X-ray crystal structures were determined. The efficiency of (R)-3 was sufficient to produce O-acetyl derivatives of aromatic cyanohydrins with ee in the range of 80-91% at -40°.