120850-92-2

Basic information

• Product Name: (1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL
• Synonyms: (R,R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL;(1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL;(1r,2r)-1,2-dicyclohexylethylene glycol;(R,R)-(-)-1,2-Dicyclohexyl-1,2-ethanediol,99%;(1R,2R)-1,2-Dicyclohexyl-1,2-ethanediol 95%
• CAS NO: 120850-92-2
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• Product Categories: Aromatic alcohols and diols
• Mol File: 120850-92-2.mol

Chemical Properties

• Melting Point: 138-142 °C(lit.)
• Boiling Point: 327.98°C (rough estimate)
• Flash Point: 179.8°C
• Appearance: /
• Density: 0.9538 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4780 (estimate)
• CAS DataBase Reference: (1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL(120850-92-2)
• EPA Substance Registry System: (1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL(120850-92-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 120850-92-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL is used as a chiral auxiliary for preparing highly diastereomerically pure alkyl boronates. Its unique chiral properties make it a valuable component in the synthesis of complex organic molecules, particularly in the pharmaceutical industry.
Used in Pharmaceutical Industry:
(1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL is used as a building block and chiral ligand in the development of new drugs and pharmaceutical compounds. Its ability to influence the stereochemistry of reactions can lead to the creation of more effective and selective medications.
Used in Chiral Catalysts:
In the field of catalysis, (1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL serves as a chiral ligand, enhancing the selectivity and efficiency of asymmetric catalytic reactions. This application is crucial in producing enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Materials Science:
(1R,2R)-(-)-1,2-DICYCLOHEXYL-1,2-ETHANEDIOL can be employed in the development of novel materials with specific properties, such as chiral polymers or liquid crystals, due to its unique chiral structure and reactivity. These materials have potential applications in various fields, including optoelectronics and sensors.

InChI:InChI=1/C14H26O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h11-16H,1-10H2/t13-,14-/m1/s1

Upstream product

• 55409-09-1 1,2-dicyclohexyl-2-hydroxy-ethanone 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 2043-61-0 cyclohexanecarbaldehyde 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 27819-71-2 2-chloro-3',4'-dimethoxybenzoin 
• 41841-04-7 2-(2-chlorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone 
• 931-50-0 cyclohexylmagnesium bromide 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 84072-32-2 1-[(Z)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 
• 144-79-6 chloromethyldiphenylsilane 
• 52340-78-0 (R,R)-hydroxybenzoin 
• 120850-91-1 (S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol 
• 181515-46-8 (R,R)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate 

Downstream Products

• 393166-59-1 [R-(4α,5β)]-4,5-dicyclohexyl-2-[(triphenylmethoxy)methyl]-1,3,2-dioxaborolane 
• 157307-27-2 [(4S,5S)-4,5-Dicyclohexyl-2-(3-cyclopropylidene-propyl)-[1,3]dioxolan-2-ylethynyl]-trimethyl-silane 
• 325141-81-9 (4R,5R)-2-[2-[[(1,1-dimethylethyl)oxy]carbonyl]ethyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane 
• 257861-22-6 acrolein (R,R)-1,2-dicyclohexylethylene acetal 
• 616227-07-7 2-aminophenylboronic acid (-)-1,2-dicyclohexyl-1,2-ethanediol ester 
• 159656-91-4 -2-methyl-4,5-dicyclohexyl-1,3,2-dioxaborolane 
• 152428-72-3 (4R,5R)-4,5-dicyclohexyl-2-ethyl-1,3,2-dioxaborolane 
• 869218-52-0 (R,R)-1,2-dicyclohexylethane-1,2-diol tert-butyl alcohol borate 
• 238088-20-5 (4R,5R)-4,5-dicyclohexyl-α-methyl-1,3,2-dioxaborolane-2-butanenitrile 
• 238088-21-6 (4R,5R)-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-butanenitrile 
• 238088-33-0 (4R,5R)-4,5-dicyclohexyl-1,3,2-dioxaborolane-2-propanenitrile 
• 238088-34-1 (4R,5R)-4,5-dicyclohexyl-α-methyl-1,3,2-dioxaborolane-2-propanenitrile 

Relevant articles and documents

Asymmetric Synthesis of Serricornin via Boronic Esters

Highly stereoselective boronic ester chemistry has been used for the synthesis of (4S,6S,7S)-7- hydroxy-4,6-dimethylnonanone (1), the pheromone of the cigarette beetle. 2-Bromo-1-butene (8) was made from 1-butyne via bromoboration and protodeboronation, and was converted to 1-ethylethenylmagnesium bromide. (R,R)-1,2-Dicyclohexyl-1,2-ethanediol ["(R)-DICHED"] methylboronate was treated with (dichloromethyl)lithium to yield (R)-DICHED (S)-1-chloroethylboronate (9), which with 1-ethylethenylmagnesium bromide yielded (R)-DICHED (R)-(2-ethyl-1-methyl-2- propenyl)boronate (10). Further chain extensions with (chloromethyl)lithium, (dichloromethyl)- lithium followed by methylmagnesium bromide, and (dichloromethyl)lithium followed by ethyl- magnesium bromide completed assembly of the carbon skeleton. Deboronation with hydrogen peroxide yielded (3S,5S,6S)-2-ethyl-3,5-dimethylocten-6-ol (14), which with osmium tetraoxide and sodium periodate yielded 1.

Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species

Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species.

Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME

The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields.

Stereospecific Pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides

We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.

Mechanistic study of half-titanocene-based reductive pinacol coupling reaction

The reductive pinacol coupling reaction of aldehydes or ketones creating a new C-C bond has been a major tool to produce 1,2-diol compounds. The reaction mechanism is known to be composed of sequential three steps (activation, coupling, and dissociation). In this work, we studied the dissociation step of half-titanocene-based catalytic systems. Cp and Cp* derivatives of the pinacolato-bridged dinuclear complex were synthesized and evaluated as possible models for intermediates from the coupling step. We monitored 1H-NMR spectra of the reaction between the metalla-pinacol intermediates and D2O. New reaction routes of the dissociation step including oxo- and pinacolato-dibridged dinuclear complexes and oxo-bridged multinuclear complexes have been suggested. Copyright

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

Reductive self-coupling reaction of imines and aldehydes induced by strontium metal

Aromatic aldimines reacted with Sr in the presence of a catalytic amount of iodine to give self-coupling products in good yields, whereas aromatic and aliphatic aldehydes underwent a similar reaction effected by the combined use of Sr and Al(OEt)3. Copyright

Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: A formal synthesis

Prins cyclization using an electron-rich benzaldehyde and a homoallylic alcohol efficiently delivered the fully substituted C-aryl tetrahydropyranoside of kendomycin. The Royal Society of Chemistry 2006.

Samarium diiodide-catalyzed diastereoselective pinacol couplings

(Chemical Equation Presented) A complex of samarium diiodide (Sml 2) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me2SiCl2 and Mg. Diastereoselectivity of up to 95/5 (±/meso) has been achieved for aliphatic aldehydes and up to 19/81 (±/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the Sml 2/tetraglyme/Mg/Me2SiCl2 catalytic system.

Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand

A new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is developed. Its chromium complex, TBOxCrCl (3 mol %), effectively catalyzes the pinacol coupling reaction of aromatic aldehydes at room temperature with high yield (up to 94%), high diast