Description

(1R)-trans-N,N’-1,2-Cyclohexanediylbis(1,1,1-trifluoromethanesulfonamide) (CAS No. 122833-60-7) is a high-purity chiral sulfonamide compound with the molecular formula C₈H₁₂F₆N₂O₄S₂. This specialized chemical features a cyclohexane backbone with two trans-oriented trifluoromethanesulfonamide groups in the (1R,2R) configuration, making it valuable for asymmetric synthesis and catalysis. The electron-withdrawing trifluoromethyl groups enhance its reactivity as a chiral auxiliary or ligand in transition metal catalysis. Supplied as a white to off-white crystalline solid with >98% purity (HPLC), this compound is ideal for pharmaceutical intermediates, organocatalysis, and materials science research. It is packaged under inert gas to ensure stability and shipped with comprehensive analytical data including ¹H/¹⁹F NMR, HPLC, and MS spectra.

Properties

• CAS Number: 122833-60-7
• Complexity: 532
• IUPAC Name: 1,1,1-trifluoro-N-[(1R,2R)-2-(trifluoromethylsulfonylamino)cyclohexyl]methanesulfonamide
• InChI: InChI=1S/C8H12F6N2O4S2/c9-7(10,11)21(17,18)15-5-3-1-2-4-6(5)16-22(19,20)8(12,13)14/h5-6,15-16H,1-4H2/t5-,6-/m1/s1
• InChI Key: GKSGSDYYIYURPD-PHDIDXHHSA-N
• Exact Mass: 378.01426819
• Molecular Formula: C8H12F6N2O4S2
• Molecular Weight: 378.3
• SMILES: C1CC[C@H]([C@@H](C1)NS(=O)(=O)C(F)(F)F)NS(=O)(=O)C(F)(F)F
• Topological: 109
• Monoisotopic Mass: 378.01426819
• Synonyms: 122833-60-7, (1R)-trans-N,N’-1,2-Cyclohexanediylbis(1,1,1-trifluoromethanesulfonamide), DTXSID40454846, DTXCID30405665, 623-938-8, 1,1,1-trifluoro-N-[(1R,2R)-2-(trifluoromethylsulfonylamino)cyclohexyl]methanesulfonamide, Methanesulfonamide, N,N’-(1R,2R)-1,2-cyclohexanediylbis[1,1,1-trifluoro-, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(1,1,1-trifluoromethanesulfonamide), 164321-91-9, (r,r)-cyclohexane, SCHEMBL2678169, 1,1,1-TRIFLUORO-N-[(1R,2R)-2-(TRIFLUOROMETHANESULFONAMIDO)CYCLOHEXYL]METHANESULFONAMIDE, Methanesulfonamide, N,N’-(1R,2R)-1,2-cyclohexanediylbis[1,1,1-trifluoro-, rel-, Methanesulfonamide,N,N’-(1R,2R)-1,2-cyclohexanediylbis[1,1,1-trifluoro-,rel-

This compound serves as a chiral building block for asymmetric synthesis of bioactive molecules and as a ligand for transition metal catalysts in enantioselective transformations. Researchers utilize its rigid cyclohexane scaffold to induce stereocontrol in C-C bond forming reactions. In medicinal chemistry, it finds application in developing fluorinated drug candidates due to its metabolic stability imparted by the trifluoromethyl groups. The compound’s bifunctional nature also enables its use in constructing supramolecular architectures.

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 (100%): 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 (100%)

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