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404438

Sigma-Aldrich

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

98%

Synonym(s):

(S,S)-Jacobsen’s ligand

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About This Item

Linear Formula:
[[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10
CAS Number:
Molecular Weight:
546.83
Beilstein/REAXYS Number:
5464823
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

optical activity

[α]20/D +315 to 15°, c = 1 in methylene chloride

mp

203-206 °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-/m0/s1

InChI key

FYNXDGNCEBQLGC-GTHUDTLPSA-N

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Application

(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.

Legal Information

Licensed through Research Corporation Technologies

pictograms

Exclamation mark

signalword

Warning

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


Certificates of Analysis (COA)

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Chang, S. et al.
Journal of the American Chemical Society, 58, 6939-6939 (1993)
E.N. Jacobsen et al.
Journal of the American Chemical Society, 113, 7063-7063 (1991)
L. Deng et al.
The Journal of Organic Chemistry, 57, 4320-4320 (1992)

Articles

Salen Ligands: In 1990, Jacobsen and Katsuki independently published the first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Chromatograms

application for HPLCapplication for HPLC

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