(1R,2R)-1,2-dicyclohexylethane-1,2-diol

• ChemBase ID: 149867
• Molecular Formular: C14H26O2
• Molecular Mass: 226.35504
• Monoisotopic Mass: 226.19328007
• SMILES: C1CCC(CC1)[C@H]([C@@H](C1CCCCC1)O)O
• Canonical SMILES: O[C@@H]([C@@H](C1CCCCC1)O)C1CCCCC1
• InChI: InChI=1S/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
• InChIKey: CKHLARJSOMXDKL-ZIAGYGMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-1,2-dicyclohexylethane-1,2-diol
• IUPAC Traditional name: (1R,2R)-1,2-dicyclohexylethane-1,2-diol
• Synonyms: (1R,2R)-1,2-Dicyclohexylethylene glycol; (1R,2R)-1,2-Dicyclohexyl-1,2-ethanediol; (1R,2R)-1,2-二环己基乙二醇; (1R,2R)-(-)-1,2-二环己基-1,2-乙二醇

Database IDs

• CAS Number: 120850-92-2
• MDL Number: MFCD00145236
• PubChem SID: 162244029; 24864898
• PubChem CID: 10633028

CALCULATED PROPERTIES

• Acid pKa: 13.655697
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.1394217
• LogD (pH = 7.4): 3.1394215
• Log P: 3.1394217
• Molar Refractivity: 65.384 cm^3
• Polarizability: 26.29487 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 138-142 °C; 138-142 °C(lit.)
• Optical Rotation: [α]20/D -2.2°, c = 0.8 in chloroform; [α]20/D -2.3±0.3°, c = 1% in chloroform stab. with amylenes

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95%
• Grade: purum
• Linear Formula: [C6H11CH(OH)-]2

DETAILS

Sigma Aldrich - 400149

Application
C2 symmetric chiral diol with versatile applications as a chiral auxiliary,1,2 building block,3,4,5 and chiral ligand.6,7 Chiral auxiliary for preparing highly diastereomerically pure alkyl boronates.8
Packaging
1 g in glass bottle

Sigma Aldrich - 36617

Other Notes
Auxiliary used in highly enantio- and diastereoselective syntheses via boronic esters1,2