(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine (CAS: 135616-40-9) is a chiral ligand with the linear formula [[(CH<sub>3</sub>)<sub>3</sub>C]<sub>2</sub>C<sub>6</sub>H<sub>2</sub>-2-(OH)CH=N]<sub>2</sub>C<sub>6</sub>H<sub>10</sub> and a molecular weight of 546.83 g/mol. Also known as (R,R)-Jacobsen’s ligand, this compound is primarily utilised in asymmetric synthesis, serving as a key component in chiral catalysts for stereoselective chemical transformations.
- IUPAC
- (R,R)-Jacobsen’s ligand
- Synonyms
- [[ (CH3)3C ]2 C6 H2 - 2 - (OH) CH = N ]2 C6 H10, (R,R)-Jacobsen’s ligand
Chiral Ligand in Asymmetric Synthesis
This compound acts as a privileged ligand, forming complexes with metal centres to facilitate enantioselective reactions. Its structure is well-suited for promoting high stereoselectivity in various catalytic processes.
Catalysis for Chemical Synthesis
It is employed as a chiral catalyst in organic synthesis, enabling the preparation of enantiomerically enriched compounds. This is crucial for the development of pharmaceuticals and fine chemicals.
Precursor for Metal Complexes
The ligand can be readily coordinated with various transition metals to generate active catalysts. These complexes are investigated for their efficacy in diverse catalytic applications.
| Molecular weight | 546.83 |
|---|---|
| Linear formula | [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10 |
| Assay | 98% |
| Optical activity | [α]20/D −315±15°, c = 1 in methylene chloride |
| Application | Amylases from Aspergillus oryzae are used to prevent staling in the baking industry, clarify haze from fruit juices and alcoholic beverages, and produce glucose and maltose syrup products.1 |
| Melting point | 205-207 °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 |
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-cyclohexanediamine used for?
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This compound is primarily used as a chiral ligand in asymmetric synthesis and as a component in chiral catalysts for stereoselective chemical transformations.
What are the CAS number and chemical formula?
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The CAS number is 135616-40-9, 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-(OH)CH=N]<sub>2</sub>C<sub>6</sub>H<sub>10</sub>.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product with an assay of 98%. We do not represent this product as USP, BP, or EP grade.
How should (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine be handled safely?
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This compound is a Warning substance, indicated by GHS07. It causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Recommended personal protective equipment includes a dust mask type N95 (US), eyeshields, and gloves. Handle in a well-ventilated area and avoid dust formation. Ensure P261 (Avoid breathing dust) and P305 + P351 + P338 (IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing) precautions are followed.
Is this chemical a controlled substance?
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The provided data does not indicate that this chemical is a controlled substance.
How is this product exported or shipped?
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Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals. Specific shipping and export details are available upon request.
How can I request a sample or quote?
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To request a sample or a quotation for (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, please contact our sales team via the website or direct inquiry channels.
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