N-[(1R,2R)-2-amino-1,2-diphenylethyl]-4-methylbenzene-1-sulfonamide

• ChemBase ID: 68120
• Molecular Formular: C21H22N2O2S
• Molecular Mass: 366.47658
• Monoisotopic Mass: 366.14019895
• SMILES: c1(ccc(cc1)C)S(=O)(=O)N[C@@H]([C@@H](c1ccccc1)N)c1ccccc1
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)N[C@@H]([C@@H](c1ccccc1)N)c1ccccc1
• InChI: InChI=1S/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/t20-,21-/m1/s1
• InChIKey: UOPFIWYXBIHPIP-NHCUHLMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1R,2R)-2-amino-1,2-diphenylethyl]-4-methylbenzene-1-sulfonamide
• IUPAC Traditional name: N-[(1R,2R)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide
• Synonyms: (R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide; (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine; (1R,2R)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine; (1R,2R)-(-)-N-(p-Tolylsulfonyl)-1,2-diphenylethylenediamine; (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine; (1R,2R)-1-Amino-2-tosylamino-1,2-diphenylethane; (1R,2R)-N-p-Toluenesulfonyl-1,2-diphenylethylenediamine; (R,R)-1,2-Diphenyl-N-(p-toluenesulfonyl)ethylenediamine; (R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine; N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide; TsDPEN; [(1R,2R)-1,2-Diphenyl-2-[[(4-tolyl)sulfonyl]amino]ethyl]amine; (1R,2R)-(-)-N-对甲苯磺酰基-1,2-二苯基乙二胺; (1R,2R)-N-(对甲苯磺酰基)-1,2-二苯基乙二胺

Database IDs

• CAS Number: 144222-34-4
• MDL Number: MFCD02093428
• PubChem SID: 24871941; 162033852
• PubChem CID: 2734565

CALCULATED PROPERTIES

• Acid pKa: 10.381595
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3019855
• LogD (pH = 7.4): 2.8230658
• Log P: 3.9369535
• Molar Refractivity: 104.6692 cm^3
• Polarizability: 41.771095 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-130°C; 128-131 °C(lit.)
• Optical Rotation: [α]20/D -35°, c = 1 in chloroform; -31 (c=1 in chloroform)

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 98%; 98+%
• Linear Formula: CH3C6H4SO2NHCH(C6H5)CH(C6H5)NH2

DETAILS

Sigma Aldrich - 484334

Packaging
1 g in glass bottle

Toronto Research Chemicals - A607875

(R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide is used as a catalyst in stereoselective preparation of aromatic ketone derivatives as well as other chiral organic compounds.

REFERENCES

• Tanis, S.P. et al.: Tetrahed. Assym., 17, 2154 (2006)
• Morris, D.J. et al.: Tetrahed. Lett., 51, 209 (2006)