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Description
TCI D4337 (S)-(-)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole, CAS 106092-09-5, is a chiral building block supplied by TCI under catalog code D4337 and belongs to the asymmetric synthesis category. Its molecule combines an aromatic thiazole ring fused to a hydrogenated cyclohexane ring, and it carries two amino groups that sit in distinctly different chemical environments. One amino group is attached to the thiazole ring, while the other resides on a saturated carbon that constitutes a stereogenic centre with the S configuration. In the laboratory, this compound serves as an enantiomerically pure scaffold for constructing target molecules that require defined stereochemical specificity.
The property that makes this material highly valued is that chirality is already defined and available from the very beginning of the synthesis. Researchers do not need to carry out racemate resolution or design a separate asymmetric catalyst, because the stereochemical information is already carried within the starting material and is transferred through to the final product. In addition, the two amino groups of differing character permit selective functionalisation: the aliphatic amine at position six is generally more nucleophilic and more readily alkylated or acylated, whereas the amine on the thiazole ring exhibits different reactivity, allowing chemists to address each nitrogen in a controlled sequence.
In Indonesian laboratories, this chiral building block is typically used in university research groups, pharmaceutical chemistry laboratories, and contract synthesis facilities working on stereochemically defined targets. It is normally handled at bench scale for multi-step synthetic routes, method development, and reference-standard preparation, where obtaining a single enantiomer reliably matters more than reaction scale. Because it removes the need for in-house resolution or bespoke catalyst development, it is a practical choice for groups with limited chiral separation infrastructure.
Laboratory Applications
- Asymmetric synthesis of stereochemically defined targets: the S configuration at the saturated carbon is fixed in the starting material, so the required stereochemistry is carried through the route without a separate resolution step.
- Chiral building block assembly in multi-step routes: the fused thiazole and hydrogenated cyclohexane framework provides a rigid, pre-formed core onto which further substituents can be elaborated by the synthetic chemist.
- Selective mono-functionalisation studies: the aliphatic amine at position six is generally more nucleophilic and more readily alkylated or acylated than the thiazole-bound amine, enabling controlled, sequential derivatisation.
- Preparation of enantiomerically pure intermediates for pharmaceutical chemistry research: the compound supplies stereochemical information directly, which is essential where biological activity depends on a single enantiomer.
- Methodology and route-development work in academic research groups: the two amino groups of differing reactivity make this molecule a useful substrate for exploring chemoselective amine protection, coupling, and derivatisation strategies.
Specifications
- Brand: TCI (catalog code D4337)
- CAS Number: 106092-09-5
- Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
- Chemical name: (S)-(-)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole
- Pack sizes: available in standard TCI research-scale packaging; please confirm the required pack size when ordering
- Storage: store according to the manufacturer's instructions stated on the product label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated place, away from heat, direct sunlight, and incompatible materials, and follow the storage conditions specified by the manufacturer on the label and safety data sheet. Keep the material in its original supplier container, or transfer it only to a clean, chemically compatible and clearly labelled container. As an amine-containing compound, it should be protected from moisture and air where practicable. Handle in a fume hood using appropriate personal protective equipment, including safety goggles, gloves, and a laboratory coat. Avoid inhalation of dust and contact with skin and eyes, wash hands thoroughly after handling, and dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
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