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

Base Information

• Chemical Name: (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE
• CAS No.: 135616-36-3
• Molecular Formula: C₃₆H₅₄N₂O₂
• Molecular Weight: 546.837
• Hs Code.: 29252900
• Mol file: 135616-36-3.mol

Synonyms:Phenol,2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)-,[1S-[1a(E),2b(E)]]-

Chemical Property of (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE

Chemical Property:

• Melting Point: 203-206 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 646.3°Cat760mmHg
• PKA: 13.06±0.40(Predicted)
• Flash Point: 115.2°C
• PSA: 65.18000
• Density: 1.03g/cm³
• LogP: 9.13700
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

(S,S)-(+)-N,N’-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: (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. (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.

Technology Process of (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE

There total 2 articles about (S,S)-(+)-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → 6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(2,4-di-tert-butylphenol) (135616-36-3)

Guidance literature:

In ethanol; for 2h; Reflux;

DOI:10.1039/c9dt04146j

Reference yield:

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + (1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate (32044-22-7,39961-95-0) → 6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(2,4-di-tert-butylphenol) (135616-36-3)

Guidance literature:

With potassium carbonate; In ethanol; water; Reflux;

DOI:10.1016/j.apcata.2009.10.041

Reference yield: 98.0%

cobalt(II) diacetate tetrahydrate (6147-53-1) + 6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(2,4-di-tert-butylphenol) (135616-36-3) → [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) (188264-84-8)

Guidance literature:

In methanol; 25°C, 5 h; recrystn. from MeOH;

DOI:10.1021/om000074j

upstream raw materials:

3,5-di-tert-butyl-2-hydroxybenzaldehyde

(S,S)-1,2-diaminocyclohexane

(1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate

Downstream raw materials:

methyl (S)-(+)-4-methylcyclohex-1-ene-4-carboxylate

[(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II)