2,4-di-tert-butyl-6-{N-[(1S,2S)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol

• ChemBase ID: 140016
• Molecular Formular: C36H54N2O2
• Molecular Mass: 546.82616
• Monoisotopic Mass: 546.41852898
• SMILES: CC(c1cc(c(c(c1)/C=N/[C@@H]1[C@H](CCCC1)/N=C/c1c(c(cc(c1)C(C)(C)C)C(C)(C)C)O)O)C(C)(C)C)(C)C
• Canonical SMILES: Oc1c(/C=N/[C@H]2CCCC[C@@H]2/N=C/c2cc(cc(c2O)C(C)(C)C)C(C)(C)C)cc(cc1C(C)(C)C)C(C)(C)C
• InChI: InChI=1S/C36H54N2O2/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12/h17-22,29-30,39-40H,13-16H2,1-12H3/t29-,30-/m0/s1
• InChIKey: FYNXDGNCEBQLGC-KYJUHHDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4-di-tert-butyl-6-{N-[(1S,2S)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol
• IUPAC Traditional name: 2,4-di-tert-butyl-6-{N-[(1S,2S)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol
• Synonyms: (S,S)-Jacobsen’s ligand; (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine; (S,S)-Jacobsen 配体; (S,S)-(+)-N,N′-双(3,5-二-叔丁基亚水杨基)-1,2-环己二胺

Database IDs

• CAS Number: 135616-36-3
• MDL Number: MFCD00191801
• Beilstein Number: 5464823
• PubChem SID: 162234261; 24865245
• PubChem CID: 10770397

CALCULATED PROPERTIES

• Acid pKa: 9.452425
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.923665
• LogD (pH = 7.4): 10.634766
• Log P: 10.66021
• Molar Refractivity: 171.9314 cm^3
• Polarizability: 65.7757 Å^3
• Polar Surface Area: 65.18 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 203-206 °C; 203-206 °C(lit.)
• Optical Rotation: [α]20/D +310±10°, c = 1% in methylene chloride; [α]20/D +315 to 15°, c = 1 in methylene chloride

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (CHN); 98%
• Grade: purum
• Linear Formula: [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10

DETAILS

Sigma Aldrich - 404438

Packaging
1, 5 g in glass bottle
Legal Information
Licensed through Research Corporation Technologies
Application
Ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.1,2,3