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
• Article Data: 22

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

Chemical Properties

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Uses

C2 symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand. Chiral auxiliary for preparing highly diastereomerically pure alkyl boronates.

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

• 2043-61-0 cyclohexanecarbaldehyde 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 931-50-0 cyclohexylmagnesium bromide 
• 7647-01-0 hydrogenchloride 
• 41841-04-7 2-(2-chlorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone 
• 64-17-5 ethanol 
• 27819-71-2 2-chloro-3',4'-dimethoxybenzoin 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 55409-09-1 1,2-dicyclohexyl-2-hydroxy-ethanone 
• 144-79-6 chloromethyldiphenylsilane 
• 84072-32-2 1-[(Z)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 
• 152428-82-5 (4R,5R)-4,5-dicyclohexyl-2-methyl-1,3,2-dioxaborolane 
• 106-51-4 p-benzoquinone 
• 316139-54-5 [2(1S),4R,5R]-4,5-dicyclohexyl-2-(1-chloro-2-phenylethyl)-1,3,2-dioxaborolane 

Downstream Products

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

Relevant articles and documents

An efficient preparation of (R *,R *)-1,2-dicyclohexylethane-1,2-diol, a superior chiral director for synthesis with boronic esters

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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.

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.

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.