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  • 404411 - (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

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404411 Sigma-Aldrich

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

98%

Synonym: (R,R)-Jacobsen’s ligand

  • CAS Number 135616-40-9

  • Linear Formula [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10

  • Molecular Weight 546.83

  •  Beilstein/REAXYS Number 5464823

  •  MDL number MFCD00191800

  •  PubChem Substance ID 24865244

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, SALENs More...
Quality Level   100
assay   98%
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.

Packaging

1, 5 g in glass bottle

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 & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

HPLC Analysis of Jacobsen Catalyst Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP (Ammonium Hydroxide Mobile Phase)

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Jacobsen Catalyst Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP (Ammonium Hydroxide Mobile Phase)
Keywords: Chromatography, High performance liquid chromatography

HPLC Analysis of Jacobsen Catalyst Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP (TEA mobile phase)

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Jacobsen Catalyst Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP (TEA mobile phase)
Keywords: Chromatography, High performance liquid chromatography

Salen Ligands

Salen molecules have been studied for more than six decades. However, in 1990 Jacobsen and Katsuki independently published the first reports of salen used as ligands with manganese for asymmetric epo...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 71.
Keywords: Addition reactions, Asymmetric synthesis, Catalysis, Epoxidations, Ligands

Peer-Reviewed Papers
15

References

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