143585-47-1

Basic information

• Product Name: (1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE
• Synonyms: (1R,2R)-1,2-N,N'-BIS[(4-TOLUENESULFONYL)AMINO]CYCLOHEXANE;(1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE;(1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLO-HE XANEDIAMINE, 98% (99% EE/HPLC);(1R,2R)-1,2-N,N''-BIS[(4-TOLUENESULFONYL)AMINO]CYCLOHEXANE, 98+%, 98+%EE;(1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine,99%e.e.
• CAS NO: 143585-47-1
• Molecular Formula: C₂₀H₂₆N₂O₄S₂
• Molecular Weight: 422.56
• Product Categories: Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Protected Amines
• Mol File: 143585-47-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 170-173 °C(lit.)
• Boiling Point: 591.4 ºC at 760 mmHg
• Flash Point: 311.5 ºC
• Appearance: /
• Density: 1.33 g/cm³
• Storage Temp.: 2-8°C
• PKA: 11.02±0.40(Predicted)
• CAS DataBase Reference: (1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(143585-47-1)
• EPA Substance Registry System: (1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE(143585-47-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 143585-47-1(Hazardous Substances Data)

Usage

General Description

(1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE is a chemical compound that has two chiral centers, denoted as 1R and 2R. It is a di-p-tosylated derivative of 1,2-cyclohexanediamine, which means that both amino groups of the cyclohexanediamine molecule are derivatized with tosyl groups. (1R,2R)-(+)-N,N'-DI-P-TOSYL-1,2-CYCLOHEXANEDIAMINE is often used in organic synthesis as a chiral auxiliary or as a resolving agent for the separation of racemic mixtures. It is also a common building block for the preparation of biologically active molecules and pharmaceuticals, as its chiral nature can influence the properties and activities of the resulting compounds.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 174291-96-4 (1R,2R)-(-)-N-p-tosyl-1,2-cyclohexanediamine 
• 10027-80-2 (1R,2R)-1,2-dicyclohexane-1,2-diamine dihydrochloride 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane tartrate 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 104-15-4 toluene-4-sulfonic acid 
• 127-65-1 chloroamine-T 
• 176298-50-3 (1S,2R)-N-(p-toluenesulfonyl)-2-amino-1-hydroxycyclohexane 
• 186144-56-9 N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester 
• 339312-77-5 N-(2-azidocyclohexyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 223704-16-3 (R,R)-N,N'-(cyclohexane-1,2-diyl)bis-<3-(p-toluenesulfonylamino)propan-1-ol> 
• 613668-24-9 (R,R)-2,5,8-tris(p-tolylsulfonyl)-2,5,8-triazabicyclo<7.4.0^1,9>tridecane 
• 308798-06-3 (1S,9S,14S,22S)-2,8,15,21-Tetrakis(p-toluenesulfonyl)-5,18-dioxa-2,8,15,21-tetraazatricyclo[20.4.0.0^9,14]hexacosane 
• 852043-13-1 C₄₂H₄₆N₂O₅S₂ 
• 852043-14-2 C₆₄H₆₆N₂O₆S₂ 
• 852043-17-5 C₄₅H₅₂N₂O₅S₂ 
• 933442-83-2 C₆₈H₉₀N₆O₁₂S₆ 
• 933442-85-4 C₇₄H₁₀₂N₆O₁₂S₆ 

Relevant articles and documents

Reversal of enantioselectivity on protonation of enol(ate)s derived from 2-methyl-1-tetralone using C2-symmetric sulfonamides

The synthesis of enantiomerically enriched (R)-2-methyl-1-tetralone 1 (64% e.e.) was achieved through protonation of its lithium enolate 3 using a C 2-symmetrical bis-sulfonamide 5d as an internal proton source. Access to the complementary (S)-enantiomer 1 (45% e.e.) can be achieved using an external quench strategy involving acetic acid as the external proton source.

Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles

We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).

A study of base-catalyzed aldol reaction of trimethylsilyl enolates

Mukaiyama-type aldol reaction of trimethylsilyl enolates with aldehydes in the presence of a base is a complicated reaction. It usually results in various products determined by the nature of base and reaction medium. The present study has been undertaken to understand these factors and design new Lewis base catalysts to optimize the yield of desired aldol product. It has been shown that mild Bronsted base with inbuilt hydrogen bonding sites are efficient catalysts for the reactions involving trimethylsilyl enolates. Based on the observed results, a mechanism is proposed to explain the reaction outcome.

Investigation of macrocyclisation routes to 1,4,7-triazacyclononanes: Efficient syntheses from 1,2-ditosylamides

Two routes to the synthesis of a cyclohexyl-fused 1,4,7-triazacyclononane involving macrocyclisations of tosamides have been investigated. In the first approach, using a classic Richman-Atkins-type cyclisation of a cyclohexyl-substituted 1,4,7-tritosamide