35018-62-3

Basic information

• Product Name: (1S-trans)-1,2-Cyclohexanediamine dihydrochloride
• Synonyms: (1S,2S)-1,2-Cyclohexanediamine hydrochloride;(1S-trans)-1,2-Cyclohexanediamine dihydrochloride;1,2-CyclohexanediaMine, N1,N2-diMethyl-, dihydrochloride, (1S,2S)-
• CAS NO: 35018-62-3
• Molecular Formula: C₆H₁₆N₂*2Cl
• Molecular Weight: 187
• Mol File: 35018-62-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S-trans)-1,2-Cyclohexanediamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-trans)-1,2-Cyclohexanediamine dihydrochloride(35018-62-3)
• EPA Substance Registry System: (1S-trans)-1,2-Cyclohexanediamine dihydrochloride(35018-62-3)

Safety Data

• Hazardous Substances Data: 35018-62-3(Hazardous Substances Data)

Usage

General Description

(1S-trans)-1,2-Cyclohexanediamine dihydrochloride is a chemical compound with the molecular formula C6H14N2?2HCl. It is a white crystalline powder that is soluble in water and ethanol. (1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used primarily in the pharmaceutical industry as an intermediate for the synthesis of various pharmaceutical drugs. It can also be used as a chiral building block in the preparation of chiral ligands and catalysts. Additionally, (1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used in the production of specialty chemicals and as a raw material in organic synthesis. Due to its versatile applications, this compound plays an important role in chemical and pharmaceutical manufacturing.

Upstream product

• 34126-95-9 2-aminocyclohexanecarboxamide 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane tartrate 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 87-69-4 L-Tartaric acid 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 116407-32-0 (1R,2R)-(-)-1,2-diammoniumcyclohexane mono-L-(+)-tartrate 
• 186144-56-9 N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester 
• 71172-32-2 1,2-dinitrocyclohexane 
• 64162-07-8 2-amino-cyclohexanecarboxylic acid ethyl ester 

Downstream Products

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 141478-36-6 N-((1S,2S)-2-aminocyclohexyl)benzamide 
• 96027-57-5 (1R,2R)-N¹-Benzoyl-N²-(2,4-dinitrophenyl)-1,2-cyclohexane diamine 
• 223704-18-5 (R,R)-N,N'-(cyclohexane-1,2-diyl)bis-<3-(p-toluenesulphonylamino)propyl methanesulphonate> 
• 223704-16-3 (R,R)-N,N'-(cyclohexane-1,2-diyl)bis-<3-(p-toluenesulfonylamino)propan-1-ol> 
• 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 
• 247095-97-2 (1S,14S)-2,6,9,13-tetrakis(p-toluenesulphonyl)-2,6,9,13-tetraazabicyclo<12.40>octadecane 
• 212555-28-7 (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine 
• 143585-47-1 (R,R)-1,2-bis(tosylamino)cyclohexane 

Relevant articles and documents

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

SYNTHESIS OF CYCLIC CARBONATES

A dimeric aluminium(salen) catalyst of formula I: herein: Y-Q is CRC1=N or CRC1RC2-NRN1, where RC1, RC2 and RN1 are independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, ether and nitro; each of the substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16, is independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, optionally substituted C3-20 heterocyclyl, ether and nitro; X1 and X2 are independently either (i) a C2-5 alkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl, or a C1-3 bisoxyalkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl or (ii) represent a divalent group selected from C5-7 arylene, C5-7 cyclic alkylene and C3-7 heterocyclylene, which may be optionally substituted; (i) (a) at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is selected from L-A, where L is a single bond or a C1-10 alkylene group and A is an ammonium group paired with a counterion selected from Cl, Br and I; and/or (b) at least one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A, where Q is either -C(=O)-O-, -C(=O)-NH-, or a single bond; and/or (ii) (a) one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is L-A', where L is as defined above and A' is a ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (b) one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A'.

Instantaneous low temperature gelation by a multicomponent organogelator liquid system based on ammonium salts

A new synergistic multicomponent organogelator liquid system (MOGLS) was discovered during the standard protocol of tartaric acid-mediated racemic resolution of (±)-trans-1,2-diaminocyclohexane. The MOGLS is formed by a 0.126 M methanolic solution of (1R,2R)-(+)-1,2-diaminocyclohexane L-tartrate and 1 equiv of concentrated hydrochloric acid. Nonreversible gelation of oxygenated and nitrogenated solvents occurs efficiently at low temperature. Several features make this system unique: (1) it is a multicomponent solution where each of the five components is required for the organogelation property; (2) the multicomponent organogelator liquid system (MOGLS) is formed by simple, small, and commercially available chiral building blocks dissolved in a well-defined solvent system (MeOH/HCl/H2O); (3) the chiral building blocks are easily amenable for further modifications in structure-property relationship studies; (4) the gelation phenomenon takes place efficiently at low temperature upon warming up the isotropic solution, conversely to the typical gel preparation protocol (gel formation upon cooling down the isotropic solution); (5) the formed organic gels are not thermoreversible in spite of the noncovalent interactions that hold the 3D-fibrillar network together.