(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine (CAS: 135616-36-3) is a chiral ligand with the molecular formula [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10 and a molecular weight of 546.83 g/mol. This compound is recognised for its role in asymmetric synthesis, particularly in the preparation of Jacobsen's catalyst, which is instrumental in the enantioselective epoxidation of olefins.
- IUPAC
- (S,S)-Jacobsen’s ligand
- Synonyms
- (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine5,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine135616-36-3[[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10(S,S)-Jacobsen’s ligand
Asymmetric Epoxidation
Serves as a key ligand in the formation of Jacobsen's catalyst, enabling the enantioselective epoxidation of unfunctionalised olefins. This is crucial for chiral synthesis in pharmaceuticals and fine chemicals.
Chiral Ligand in Catalysis
Acts as a privileged ligand for transition metal complexes. Its chiral structure facilitates stereoselective transformations, making it valuable in advanced organic synthesis.
Chemical Synthesis
Utilised as a building block and catalyst component in various chemical synthesis pathways requiring precise stereochemical control. Its application extends to the development of novel synthetic methodologies.
| Molecular weight | 546.83 |
|---|---|
| Linear formula | [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10 |
| Assay | 98% |
| Optical activity | [α]20/D +315 to 15°, c = 1 in methylene chloride |
| Application | Ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.1,2,3 |
| Melting point | 203-206 °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 (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine used for?
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(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is primarily used as a ligand for preparing Jacobsen's catalyst, which is suitable for the enantioselective epoxidation of olefins lacking functional groups. It is a key component in asymmetric synthesis and chiral catalysis.
What are the CAS number and molecular formula?
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The CAS number for (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is 135616-36-3. The molecular formula is [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of 98%. It is supplied for research and chemical synthesis purposes and is not represented as USP, BP, EP, or any other pharmacopoeia grade.
How should (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine be handled?
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This compound is a Warning product and causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Ensure adequate ventilation, wear a dust mask (type N95 US recommended), eyeshields, and gloves. Avoid breathing dust.
How is this chemical packed, shipped, and exported?
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Tech Serve Solutions, established in 1998, is a specialist global supplier and exporter of fine chemicals. Products are carefully packed according to international shipping regulations for safe transit worldwide. Specific packing details are available upon request.
How can I request a sample or quote?
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To request a sample or obtain a quotation for (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, please contact our sales department via the website or direct email. Please specify the required quantity and destination.
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