Description

(2R)-Bornane-10,2-sultam (CAS No. 108448-77-7) is a high-purity chiral sultam derivative with the molecular formula C₁₀H₁₇NO₂S. Its IUPAC name is 10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane 3,3-dioxide. This bicyclic sulfonamide compound is widely utilized as a chiral auxiliary in asymmetric synthesis, offering excellent stereocontrol in reactions such as alkylations, aldol additions, and Michael reactions. The (2R)-configuration ensures compatibility with enantioselective methodologies, making it a valuable tool for pharmaceutical and fine chemical research. Supplied as a white to off-white crystalline solid, it is characterized by high chemical stability and solubility in common organic solvents. Each batch undergoes rigorous QC testing (HPLC, NMR) to guarantee ≥98% purity, meeting the stringent demands of synthetic chemists and process developers.

Properties

• CAS Number: 108448-77-7
• Complexity: 381
• IUPAC Name: 10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
• InChI: InChI=1S/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3
• InChI Key: DPJYJNYYDJOJNO-UHFFFAOYSA-N
• Exact Mass: 215.09799996
• Molecular Formula: C10H17NO2S
• Molecular Weight: 215.31
• SMILES: CC1(C2CCC13CS(=O)(=O)NC3C2)C
• Topological: 54.6
• Monoisotopic Mass: 215.09799996
• Synonyms: (2R)-Bornane-10,2-sultam, 94594-90-8, dpjyjnyydjojno-uhfffaoysa-n, 108448-77-7, (2S)-Bornane-10,2-sultam, (1R)-(+)-2,10-Camphorsultam, 153153-41-4, 10,10-Dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.0,1,5]decane-3,3-dione, 10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide, (1S)-(-)-2,10-Camphorsultam, MFCD00066271, 10,10-dimethyl-3-thia-4-azatricyclo[5.2.1.0~1,5~]decane3,3-dioxide, bornane-10,2-sultam, D-2,10-Camphorsultam, MLS000547527, SCHEMBL685973, SCHEMBL4250589, CHEMBL1536595, HMS2279P14, 8,8-Dimethylhexahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide, STL325060, AKOS015964038, AB88148, AC-5704, SMR000113261, SY004517, SY004518, DB-011639, ST50989913, EN300-295953, AD-266/40647167, 8,8-dimethylhexahydro-3a,6-methano-2,1-benzothiazole 2,2-dioxide, 10,10-dimethyl-3-thia-4-azatricyclo[5.2.1.0]decane-3,3-dione, (1R)-(+)-2,10-Camphorsultam; [3aR-(3aalpha,6alpha,7abeta)]-Hexahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazole, (1S)-(-)-2,10-Camphorsultam; [3aS-(3aalpha,6alpha,7abeta)]-Hexahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazole;(-)-10,2-Camphorsultam

Application

(2R)-Bornane-10,2-sultam serves as a versatile chiral auxiliary in asymmetric C-C bond-forming reactions, enabling the synthesis of enantiomerically pure intermediates for APIs. It is particularly effective in diastereoselective enolate alkylations and cycloadditions. Researchers also employ it as a ligand precursor for transition metal catalysts in enantioselective hydrogenations. Its rigid bicyclic structure enhances stereochemical outcomes in natural product synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.8%)

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