An official website of the United States government

(R,R)-Jacobsen's catalyst

PubChem CID
73602790
Structure
(R,R)-Jacobsen's catalyst_small.png
(R,R)-Jacobsen's catalyst_3D_Structure.png
Molecular Formula
Synonyms
  • (R,R)-Jacobsen's catalyst
  • 138124-32-0
  • Jacobsen's catalyst
  • Jacobsen's catalyst [MI]
  • (R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride
Molecular Weight
635.2 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2014-05-11
  • Modify:
    2025-01-18

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(R,R)-Jacobsen's catalyst.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-oxidophenyl)methylideneamino]cyclohexyl]iminomethyl]phenolate;manganese(3+);chloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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/t29-,30-;;/m1../s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

LJVAWOSDJSQANR-SEILFYAJSA-K
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C)(C)C1=CC(=C(C(=C1)C(C)(C)C)[O-])C=N[C@@H]2CCCC[C@H]2N=CC3=C(C(=CC(=C3)C(C)(C)C)C(C)(C)C)[O-].[Cl-].[Mn+3]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C36H52ClMnN2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

138124-32-0
149656-63-3

2.3.2 UNII

2.3.3 Wikidata

2.3.4 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
635.2 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
634.309775 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
634.309775 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
70.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
42
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
793
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Dark brown powder; [Sigma-Aldrich MSDS]

3.3 Chemical Classes

Metals -> Manganese Compounds, Inorganic

5 Chemical Vendors

6 Use and Manufacturing

6.1 Uses

Sources/Uses
Used as a chiral catalyst for the epoxidation of olefins; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 Hazards Summary

A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Manganese and the linked occupational diseases.

7.2 Exposure Control and Personal Protection

Maximum Allowable Concentration (MAK)
0.2 [mg/m3], as Mn (inhalable fraction), 0.02 mg/m3, as Mn (respirable fraction)[German Research Foundation (DFG)]

7.2.1 Threshold Limit Values (TLV)

0.02 [mg/m3], as Mn (respirable fraction), 0.1 mg/m3, as Mn (inhalable fraction)

8 Toxicity

8.1 Toxicological Information

8.1.1 Adverse Effects

Neurotoxin - Parkinsonism

9 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Manganese, chronic toxic effect [Category: Metal Poisoning, Occupational]

10 Literature

10.1 Consolidated References

10.2 Chemical Co-Occurrences in Literature

10.3 Chemical-Gene Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 Chemical Co-Occurrences in Patents

11.3 Chemical-Disease Co-Occurrences in Patents

11.4 Chemical-Gene Co-Occurrences in Patents

12 Classification

12.1 ChemIDplus

12.2 UN GHS Classification

12.3 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. ChemIDplus
    (N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine)manganese(III) chloride, (R,R)-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0138124320
    (N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine)manganese(III) chloride, (R,R)-rel-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0149656633
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
    (N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE)MANGANESE(III) CHLORIDE, (R,R)-
    https://gsrs.ncats.nih.gov/ginas/app/beta/substances/WPP775Y8PO
    (N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE)-1,2-CYCLOHEXANEDIAMINE)MANGANESE(III) CHLORIDE, (R,R)-REL-
    https://gsrs.ncats.nih.gov/ginas/app/beta/substances/45S483EOVD
  3. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    (R,R)-Jacobsen's catalyst
    https://haz-map.com/Agents/19130
  4. Wikidata
  5. Wikipedia
  6. PubChem
  7. GHS Classification (UNECE)
  8. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS