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404454

Sigma-Aldrich

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

Synonym(s):

(S,S)-Jacobsen’s catalyst

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About This Item

Linear Formula:
[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl
CAS Number:
Molecular Weight:
635.20
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

mp

330-332 °C (lit.)

SMILES string

CC(C)(C)c1cc2C=[N@@H]3[C@H]4CCCC[C@@H]4[N@H]5=Cc6cc(cc(c6O[Mn]35(Cl)Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C36H54N2O2.ClH.Mn/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;1H;/q;;+3/p-3/b37-21+,38-22+;;/t29-,30-;;/m0../s1

InChI key

LJVAWOSDJSQANR-RUIQGICGSA-K

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General description

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride is a metal-salen complex that can catalyze a variety of asymmetric transformations.

Application

Reactant involved in:
  • Studies of intercalative binding with ct-DNA and radical scavenging antioxidant activity
  • Immobilization on phenoxy-modified zirconium poly(styrenephenylvinylphosphonate)
  • Synthesis of derivatvies for studies of conformational models of enantioselective reactions

Catalyst involved in:
  • Asymmetric epoxidation of olefins
  • Immobilization on ionic liquid modified mesoporous silica for oxidative kinetic resolution of racemic secondary alcohols†
  • Immobilization on diamine modified zirconium olig-styrenyl phosphonate hydrogen phosphate for epoxidation of styrene
Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins. High enantioselectivities and yields are obtained for a variety of substrates, especially cis-alkenes. A few applications include the synthesis of the taxol side chain and cis-1-amino-2-indanol. Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers. Catalyst for the enantioselective epoxidation of a variety of olefins.

Legal Information

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

404454-VAR:
404454-5G:
404454-1G:
404454-BULK:
404454-25G:


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Senanayake, C.H. et al.
Tetrahedron Letters, 37, 3271-3271 (1996)
Lee, N.H. et al.
Tetrahedron Letters, 32, 5055-5055 (1991)
Zhang, W. Jacobsen, E.N.
The Journal of Organic Chemistry, 56, 2296-2296 (1991)
Senanayake, C.H. et al.
Tetrahedron Letters, 36, 3993-3993 (1995)
Journal of the American Chemical Society, 113, 7063-7063 (1991)

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