404411

(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

98%

• Synonym(s): (R,R)-Jacobsen’s ligand
• Linear Formula: [[(CH₃)₃C]₂C₆H₂-2-(OH)CH=N]₂C₆H₁₀
• CAS Number: 135616-40-9
• Molecular Weight: 546.83
• Beilstein/REAXYS Number: 5464823
• MDL number: MFCD00191800
• UNSPSC Code: 12352116
• PubChem Substance ID: 24865244
• NACRES: NA.22

Properties

• assay: 98%
• form: solid
• optical activity: [α]20/D −315±15°, c = 1 in methylene chloride
• mp: 205-207 °C (lit.)
• SMILES string: CC(C)(C)c1cc(\C=N\[C@@H]2CCCC[C@H]2\N=C\c3cc(cc(c3O)C(C)(C)C)C(C)(C)C)c(O)c(c1)C(C)(C)C
• 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/b37-21+,38-22+/t29-,30-/m1/s1
• InChI key: FYNXDGNCEBQLGC-LQWPWIHBSA-N

Description

Application

Amylases from Aspergillus oryzae are used to prevent staling in the baking industry, clarify haze from fruit juices and alcoholic beverages, and produce glucose and maltose syrup products.

Versatile ligand for asymmetric catalysis. Ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.

Lipases are used industrially for the resolution of chiral compounds and the transesterification production of biodiesel.

Biochem/physiol Actions

α-amylase catalyzes the hydrolysis of internal α-1,4-O-glycosidic bonds in starches to release α-anomeric sugars.

Lipases catalyze the hydrolysis of triacylglycerols into glycerol and free fatty acids.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves