212555-28-7

Basic information

• Product Name: (1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE
• Synonyms: (1S,2S)-1,2-N,N'-BIS((4-TOLUENESULFONYL)AMINO)-CYCLOHEXANE;(1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE;(1S,2S)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine,99%e.e.
• CAS NO: 212555-28-7
• Molecular Formula: C₂₀H₂₆N₂O₄S₂
• Molecular Weight: 422.56
• Product Categories: HydrogenationChiral Building Blocks;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Organic Building Blocks;Polyamines
• Mol File: 212555-28-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 170-173 °C(lit.)
• Boiling Point: 591.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.02±0.40(Predicted)
• CAS DataBase Reference: (1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(212555-28-7)
• EPA Substance Registry System: (1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(212555-28-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 212555-28-7(Hazardous Substances Data)

Usage

General Description

"(1S,2S)-(-)-N,N-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE" is a chiral chemical compound known for its significant role in organic chemistry, particularly in stereoselective synthesis. Structurally, this compound comprises a cyclohexane ring, which forms the core backbone, with two amine groups undergoing tosylation (p-toluenesulfonylation). In terms of its stereochemistry, this chemical compound exists as a pair of enantiomers, namely (1S,2S) and (1R,2R), indicating their mirror-image non-superimposable structure. This chemical exhibits chirality due to the different possible spatial arrangements of its constituent atoms and groups. It is predominantly used in research or academic settings rather than having any direct consumer or industrial applications.

Upstream product

• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 98-59-9 p-toluenesulfonyl chloride 
• 35018-62-3 (+)-(S,S)-trans-1,2-cyclohexanediamine dihydrochloride 
• 174291-97-5 N-[(1S,2S)-2-aminocyclohexan-1-yl]-4-methylbenzenesulfonamide 
• 871086-12-3 4-Methyl-N-[(1S,2S)-2-((R)-1-phenyl-ethylamino)-cyclohexyl]-benzenesulfonamide 
• 68820-12-2 cyclohexyl-N-tosyl aziridine 

Downstream Products

• 247096-02-2 (1S,7S,12S,18S)-2,6,13,17-tetrakis(p-toluenesulphonyl)-2,6,13,17-tetraazatricyclo<16.4.0.0^7,12>docosane 
• 1014624-54-4 (R,R,S,S,R,R)-BnNC₄H₆(OP((PhSO₂N)2C₆H₁₀))2 
• 1014624-56-6 (R,R,S,S,S,S)-BnNC₄H₆(OP((PhSO₂N)2C₆H₁₀))(OP((TolSO₂N)2C₆H₁₀)) 
• 1014624-58-8 (S,S,S,S,S,S)-BnNC₄H₆(OP((TolSO₂N)2C₆H₁₀))2 
• 933442-86-5 C₇₄H₁₀₂N₆O₁₂S₆ 
• 933442-84-3 C₆₈H₉₀N₆O₁₂S₆ 
• 247095-97-2 (1S,14S)-2,6,9,13-tetrakis(p-toluenesulphonyl)-2,6,9,13-tetraazabicyclo<12.40>octadecane 
• 929078-51-3 (S,S)-2,5,8-tris(p-tolylsulfonyl)-2,5,8-triazabicyclo<7.4.0^1,9>tridecane 

Relevant articles and documents

Synthesis of Chiral Vicinal Diamines by Silver(I)-Catalyzed Enantioselective Aminolysis of N-Tosylaziridines

The kinetic resolution of 2-aryl-N-tosylaziridines and the asymmetric desymmetrization of meso-N-tosylaziridines by ring openings with various primary and secondary anilines, and aliphatic amines as nucleophile have been realized by using a single silver(I)/chiral diphosphine complex as catalyst for the first time. The simple starting materials, broad scope, and easy scalability render this protocol a practical way to chiral vicinal diamine derivatives.

Synthesis of chiral vicinal C2 symmetric and unsymmetric bis(sulfonamide) ligands based on trans-1,2-cyclohexanediamine by aminolysis of N-tosylaziridines

The ring opening of N-tosylaziridines with aliphatic amines can be efficiently catalyzed by lithium perchlorate to provide derivatives of the trans-1,2-diamine in high yields. The reaction was used in desymmetrization of several cyclic N-tosylaziridines using chiral amines. Using this strategy, an efficient synthesis of chiral vicinal C2 symmetric bis(sulfonamide) and unsymmetrical bis(sulfonamide) ligands based on trans-1,2-cyclohexanediamine was developed.

Optically active tetraazamacrocycles analogous to cyclam

The syntheses of enantiopure tetraazamacrocycles analogous to cyclam, (S,S)-3, (R,R)-3 and (S,S,S,S)-4, have been carried out. NMR and semiempirical studies of 3 have revealed that this compound presents a rigid conformation with C2 symmetry, w