1121-22-8

Basic information

• Product Name: (+/-)-trans-1,2-Diaminocyclohexane
• Synonyms: TIMTEC-BB SBB007639;(+/-)-TRANS-1,2-CYCLOHEXANEDIAMINE;TRANS-1,2-CYCLOHEXANEDIAMINE;1,2-Cyclohexanediamine, trans-;trans-1,2-Cyclohexaneiamine;Cyclohexanediamine;Trans-(L)-1,2-Diaminecyclohexane;trans-1,2-Diaminocyclohexane(Racemic)
• CAS NO: 1121-22-8
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: -0
• Mol File: 1121-22-8.mol

Chemical Properties

• Melting Point: 14-15 °C(lit.)
• Boiling Point: 79-81 °C15 mm Hg(lit.)
• Flash Point: 156 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.951 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.489(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.94(at 20℃)
• Water Solubility: Soluble
• Sensitive: Air Sensitive
• BRN: 506142
• CAS DataBase Reference: (+/-)-trans-1,2-Diaminocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-trans-1,2-Diaminocyclohexane(1121-22-8)
• EPA Substance Registry System: (+/-)-trans-1,2-Diaminocyclohexane(1121-22-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• F: 10-34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1121-22-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(+/-)-trans-1,2-Diaminocyclohexane is used as a key component in the synthesis of macrocyclic [3+3] hexa Schiff bases. These compounds have a wide range of applications in various fields, including pharmaceuticals, materials science, and catalysis.
Used in Chiral Ligands and Auxiliaries:
(+/-)-trans-1,2-Diaminocyclohexane is employed as a chiral ligand in asymmetric catalysis, which is an essential process in the synthesis of enantiomerically pure compounds. These compounds are crucial in the pharmaceutical industry, as they often exhibit different biological activities and are required for the development of many drugs.
Used in Chiral Stationary Phases:
(+/-)-trans-1,2-Diaminocyclohexane is also used in the preparation of chiral stationary phases, which are essential in the separation and analysis of enantiomers. This application is particularly relevant in the pharmaceutical and agrochemical industries, where the purity and stereochemistry of compounds are critical.
Used in Multidentate Ligand Preparation:
(+/-)-trans-1,2-Diaminocyclohexane is utilized in the synthesis of multidentate ligands, which are complex molecules that can bind to a central metal ion through multiple donor atoms. These ligands are vital in various fields, including catalysis, supramolecular chemistry, and materials science.
Used in [2+2] Macrocyclization:
(+/-)-trans-1,2-Diaminocyclohexane is used to prepare [2+2] macrocyclization products by reacting with aliphatic dialdehydes. Macrocyclic compounds have unique properties and are used in various applications, such as molecular recognition, drug delivery, and catalysis.

Purification Methods

Purify and store the diamine as for the cis-isomer above as it is a strong base and becomes yellow on storage. [Beilstein 13 IV 1.]

InChI:InChI=1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1

Upstream product

• 286-18-0 7-azabicyclo[4.1.0]heptane 
• 492-99-9 1,2-cyclohexanedionedioxime 
• 2802-07-5 1,3-cyclohexanedionedioxime 
• 71172-32-2 trans-1,2-dinitrocyclohexane 
• 108-45-2 m-phenylenediamine 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 110-83-8 cyclohexene 
• 286-18-0 7-azabicyclo<4.1.0>heptane 
• 286-20-4 cyclohexane-1,2-epoxide 
• 50-00-0 formaldehyd 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 109-99-9 tetrahydrofuran 
• 142-68-7 TETRAHYDROPYRANE 
• 96-47-9 2-methyltetrahydrofuran 

Downstream Products

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 30086-64-7 (3aS,7aS)-hexahydro-1H-benzo[d]imidazole-2(3H)-thione 
• 30086-64-7 trans-2-thiohexahydrobenzimidazole 
• 1121-22-8 trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine 
• 133725-75-4 N-tert-butoxycarbonyl-N'-(trans-2-aminocyclohexyl)-p-nitrophenylalaninamide 
• 119492-53-4 (R)-trans-N,N'-dipyridoxylidene-1,2-cyclohexanediamine 
• 1123-97-3 (rac)-trans-4,5-tetramethyleneimidazolidin-2-one 
• 135039-14-4 trans-N,N'-Bis(2-aminocyclohexyl)propanediamide 
• 80384-92-5 N,N,N',N'-tetrakis(2-pyridylmethyl)-trans-1,2-cyclohexanediamine 
• 130719-53-8 N¹-<3-(4-Chlorphenyl)-4-phenylisoxazol-5-yl>-1,2-diaminocyclohexan 
• 111042-16-1 3-Phenyl-5,6-cyclohexano-5,6-dihydro-2(1H)-pyrazinone-O-methyloxime 

Relevant articles and documents

Method for synthesizing trans-cyclohexyldiamine

The invention discloses a method for synthesizing trans-cyclohexyldiamine. The method comprises the following steps: by using epoxy cyclohexane as the raw material, carrying out ring opening with ammonia water, adding sulfuric acid for dewatering and salification, adding free alkali, carrying out ring opening with ammonia water, and distilling to obtain the trans-cyclohexyldiamine. The method has the advantages of high repetitiveness of the synthesis route, and simple and accessible raw materials, and provides an alternative scheme for obtaining the trans-cyclohexyldiamine pure product.

The stereospecific addition of hydroxylamines to α,β-unsaturated sulfones, nitriles and nitro compounds

N-Alkyl hydroxylamines have been shown to undergo a highly stereospecific cis addition to α,β-unsaturated sulfones, nitriles and nitro compounds.

A diamine-exchange reaction of dihydropyrazines

Dihydropyrazines reacted with 1,2-diamines to form tetraazadecalins as intermediates, and then the reaction proceeded forward to dissociate into alternate dihydropyrazine and diamine, or backward to dissociate into the starting materials in certain equilibrium. The product distribution is controlled by diamine-exchange equilibrium reaction. The various equilibrium reactions were analyzed by NMR spectroscopy.

Lithium diisopropylamide solvated by monodentate and bidentate ligands: Solution structures and ligand binding constants

6Li and 15N NMR spectroscopic studies of lithium diisopropylamide ([6Li]LDA and [6Li,15N]LDA) in toluene/pentane solutions containing a variety of mono- and polydentate ligands are reported. LDA forms exclusively dimers in the presence of n-BuOMe, Et2O, t-BuOMe, THF, 2- methyltetrahydrofuran, 2,2-dimethyltetrahydrofuran, tetrahydropyran, dimethoxyethane, N,N,N',N'-tetramethylethylenediamine, and MeOCH2CH2NR2 (NR2 = NMe2, NEt2, pyrrolidino). Addition of 1,2-dipyrrolidinoethane and (2-pyrrolidinoethyl)dimethylamine provides monomer-dimer mixtures. Treatment of LDA with trans-N,N,N',N'-tetramethylcyclohexanediamine (TMCDA) or trans- 1-(dimethyl-amino)-2-isopropoxycyclohexane in hydrocarbons afford exclusively monomers. Sparteine binds only reluctantly, giving a mixture of unsolvated oligomers and monomer. Competitions of the ethereal ligands vs TMCDA afford binding constants and associated free energies for dimer solvation which are correlated with those obtained previously for lithium hexamethyldisilazide.

Diastereo- and enantioselective synthesis of vicinal diamines via aza-Michael addition to nitroalkenes

The asymmetric synthesis of protected 1,2-diamines 4 by aza-analogous Michael addition of (-)-(2S,3R,4R,5S)-1-amino-3,4-dimethoxy-2,5-bis(methoxymethyl)pyrrolid ine (ADMP) to nitroalkenes 1 in good overall yields and high enantiomeric excesses (ee = 93-96%) is described. The auxiliary constitutes a novel chiral equivalent of ammonia and is removed under reductive N-N bond cleavage with Raney nickel, which also reduces the nitro group. The absolute configuration was determined by NMR-spectroscopic methods and polarimetry.

THE REACTIONS OF N,N-DIMETHYLPHOSPHORAMIDIC DIFLUORIDE WITH TRANS-2-SUBSTITUTED CYCLOALKANOLS

An interaction between N,N-dimethylphosphoramidic difluoride and cyclic alcohols containing hydroxyl, alkylamine and methylthiol groups in the trans-β-position was performed. Trans-1-ethylcyclopentane-1,2-diol and trans-2-(N-alkylamino)cyclopentanols react with N,N-dimethylphosphoramidic difluoride to yield 1-ethyl-6-oxabicyclo(3.1.0)hexane and 6-alkyl-6-azabicyclo(3.1.0)hexane, respectively. In the case of trans-2-(N,N-dialkylamino)cyclopentanols and cyclohexanols, such reaction gives a salt of phosphorodifluoridic acid and the corresponding cyclic N,N,N',N'-tetraalkyl-1,2-diamine whereas trans-2-methylthiocyclopentanol is converted to a salt of phosphorodifluoridic acid and N,N-dimethyl-N-(2-methylthiocyclopentyl)amine. Some of described reactions appear to be applicable for the synthesis of various organic compounds, e.g. phosphorylated 2-N,N-dialkylaminocyclopentanethiols. Key words: N,N-dimethylphosphoramidic difluoride, N,N-dimethylphosphoramidothioic difluoride, phosphorodifluoridic acid, phosphorylated dialkylaminocyclopentanethiol, N,N-dialkylaminocycloalkanol, N,N,N',N'-tetraalkyl-1,2-diamine.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.