174291-97-5

Basic information

• Product Name: (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE
• Synonyms: (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE;(1S,2S)-N-p-Tosyl-1,2-cyclohexanediamine,99%e.e.;Benzenesulfonamide, N-[(1S,2S)-2-aminocyclohexyl]-4-methyl-
• CAS NO: 174291-97-5
• Molecular Formula: C₁₃H₂₀N₂O₂S
• Molecular Weight: 268.3751
• Mol File: 174291-97-5.mol

Chemical Properties

• Melting Point: 106-110°C
• Boiling Point: 417.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 11.69±0.40(Predicted)
• CAS DataBase Reference: (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE(174291-97-5)
• EPA Substance Registry System: (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE(174291-97-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• WGK Germany: 3
• Hazardous Substances Data: 174291-97-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE is utilized as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry is essential for the development of drugs with specific biological activities, ensuring targeted effects and minimizing side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE serves as a key component in the synthesis of chiral agrochemicals. (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE's ability to influence the stereochemistry of the final product is crucial for enhancing the efficacy and selectivity of these chemicals in agricultural applications.
Used in Medicinal Chemistry Research:
(1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE is employed as a valuable tool in medicinal chemistry research. It aids in the asymmetric synthesis of complex molecules, which is vital for understanding the relationship between molecular structure and biological activity, thereby contributing to the discovery of new therapeutic agents.
Used in Organic Synthesis:
As a chiral building block, (1S,2S)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIAMINOCYCLOHEXANE is extensively used in organic synthesis for the preparation of enantiomerically pure compounds. Its strong leaving group property makes it suitable for substitution reactions, facilitating the creation of a wide range of chiral molecules with potential applications in various industries.

Upstream product

• 871086-12-3 4-Methyl-N-[(1S,2S)-2-((R)-1-phenyl-ethylamino)-cyclohexyl]-benzenesulfonamide 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 98-59-9 p-toluenesulfonyl chloride 
• 32044-22-7 (R,R)-1,2-diammoniumcyclohexane mono-(+)-tartrate salt 
• 68820-12-2 cyclohexyl-N-tosyl aziridine 

Downstream Products

• 212555-28-7 (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine 
• 192057-12-8 [chloro((S,S)-trans-N-(p-toluenesulfonyl)-1,2-diaminecyclohexane)(η6-(p-isopropyltoluene))ruthenium(II)] 
• 1234856-67-7 C₄₀H₄₇N₅O₆S₂ 
• 1265177-72-7 2,2'-bis{N-[(1S,2S)-2-(4-methylbenzenesulfonamido)cyclohexan-1-yl]carbamoyl}diphenyl sulfide 
• 1384518-61-9 (S, S, S, S)-N, N'-bis(2-(p-toluenesulfonylamino)cyclohexyl)ethylenediamine 
• 1384518-62-0 (S,S,S,S)-N,N'-bis(2-(p-toluenesulfonylamino)cyclohexyl)trimethylenediamine 

Relevant articles and documents

Asymmetric synthesis of polysubstituted 4-amino- and 3,4-diaminochromanes with a chiral multifunctional organocatalyst

A series of multifunctional catalysts with two chiral diaminocyclohexane units were developed and successfully applied in the asymmetric oxa-Michael-aza-Henry cascade reaction of salicylaldimines with nitroolefins. This approach provides a simple and effi

New C2-symmetric chiral tetraaza ligands and their application for [Ru(p -cymene)Cl2]2-catalyzed asymmetric transfer hydrogenation

Two new chiral ligands (S, S, S, S)-N, N'-bis(2-p-toluene- sulfonylaminocyclohexyl) ethylenediamine (2a) and (S, S, S, S)-N, N'-bis(2-p-toluenesulfonylaminocyclohexyl) trimethylenediamine (2b) were prepared and confirmed by means of elemental analysis, IR

Enantioselective organocatalytic Biginelli reaction: Dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality

From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to pro

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.

Reaction of allylsilanes and allylstannanes with alkynes catalyzed by electrophilic late transition metal chlorides

The intramolecular reaction of allylsilanes and allylstannanes with alkynes proceeds catalytically in the presence of Pt(II), Pd(II), Ru(II), and Au(III) chlorides. Although more limited, AgOTf also catalyzes the cyclization. Usually, PtCl2 as the catalyst in methanol or acetone gives the best results. The reaction proceeds by exo attack of the allyl nucleophile on the alkyne to form five- or six-membered ring carbocycles. The reaction generally proceeds with anti stereoselectivity. However, a terminally substituted trimethylsilyl derivative reacts by a syn-type addition. The intermediate alkenylpalladium complex has been trapped with allyl chloride to form an allylated derivative with an additional carbon-carbon bond.

Synthesis of chiral sulfonamide/Schiff base ligands

We report a facile two step synthesis of chiral ligands for bonding to transition metals. The ligands are easily prepared from trans, 1,2- diaminocyclohexane by reaction with sulfonyl chlorides to give amino- sulfonamide compounds. These intermediates are

(Hexahydrobenzimidazol-2-yl)benzophenones and derivatives

(Hexahydrobenzimidazol-2-yl)benzophenones are prepared by reaction of the ψ-acid chloride of an o-aroyl benzoic acid with an N-monotosyl-1,2-diaminocyclohexane, and heating the resulting benzoyl benzamide product with sulfuric acid. The intermediate benzo