(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride
(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride (CAS: 138124-32-0) is a chiral manganese complex with the linear formula [[[(CH<sub>3</sub>)<sub>3</sub>C]<sub>2</sub>C<sub>6</sub>H<sub>2</sub>-2-(O-)CH=N]<sub>2</sub>C<sub>6</sub>H<sub>10</sub>]MnCl. This compound is a highly effective chiral catalyst, primarily utilised in asymmetric synthesis for enantioselective epoxidation of olefins and asymmetric α-hydroxylation of silyl enol ethers. Its applications are crucial in the synthesis of complex molecules, including pharmaceutical intermediates.
- IUPAC
- (R,R)-Jacobsen’s catalyst,Jacobsen’s catalyst
- Synonyms
- (R,R)-Jacobsen’s catalystJacobsen’s catalyst[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl
Asymmetric Epoxidation
This manganese complex serves as a chiral catalyst for the asymmetric epoxidation of unfunctionalised olefins, achieving high enantioselectivities and yields, particularly for cis-alkenes. It is instrumental in synthesising chiral epoxides.
Asymmetric α-Hydroxylation
The catalyst is employed in the enantioselective α-hydroxylation of silyl enol ethers. This reaction is valuable for introducing chirality adjacent to carbonyl groups in organic synthesis.
Synthesis of Pharmaceutical Intermediates
Its ability to achieve high stereoselectivity makes it a key reagent in the synthesis of complex chiral molecules, such as the side chain of Taxol and chiral amino alcohols like cis-1-amino-2-indanol.
| Molecular weight | 635.20 |
|---|---|
| Linear formula | [[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl |
| Application | Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins.1,2,3,4 High enantioselectivities and yields are obtained for a variety of substrates1, especially cis-alkenes. A few applications include the synthesis of the taxol side chain5 and cis-1-amino-2-indanol.6,7 Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers.8 Catalyst for the enantioselective epoxidation of a variety of olefins.8,9 |
| Melting point | 330-332 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride used for?
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This compound is primarily used as a chiral catalyst in asymmetric synthesis, notably for the enantioselective epoxidation of olefins and the asymmetric α-hydroxylation of silyl enol ethers.
What is the CAS number and molecular formula for this manganese complex?
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The CAS number is 138124-32-0 and the linear formula is [[[(CH<sub>3</sub>)<sub>3</sub>C]<sub>2</sub>C<sub>6</sub>H<sub>2</sub>-2-(O-)CH=N]<sub>2</sub>C<sub>6</sub>H<sub>10</sub>]MnCl.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product for research and chemical synthesis purposes. The specific grade and purity will be detailed on the Certificate of Analysis provided with your order. We do not represent this product as USP, BP, EP, or other pharmacopoeia grades.
How should (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride be handled safely?
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This compound is classified as an irritant (H315, H319, H335). Handle with appropriate personal protective equipment, including a dust mask (type N95), eyeshields, and gloves. Ensure adequate ventilation and avoid breathing dust. In case of eye contact, rinse thoroughly with water and seek medical advice.
Can Tech Serve Solutions export this chemical?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including this product, and can fulfil international orders.
How can I request a quote or sample for this product?
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To request a quote or sample, please contact our sales department through the website or by phone, providing the product name and CAS number (138124-32-0).
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