(2R)-2-cyclohexyl-2-hydroxyacetic acid

• ChemBase ID: 150902
• Molecular Formular: C8H14O3
• Molecular Mass: 158.19496
• Monoisotopic Mass: 158.09429431
• SMILES: C1CCC(CC1)[C@H](C(=O)O)O
• Canonical SMILES: O[C@@H](C(=O)O)C1CCCCC1
• InChI: InChI=1S/C8H14O3/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7,9H,1-5H2,(H,10,11)/t7-/m1/s1
• InChIKey: RRDPWAPIJGSANI-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-cyclohexyl-2-hydroxyacetic acid
• IUPAC Traditional name: (R)-cyclohexyl(hydroxy)acetic acid
• Synonyms: (R)-(-)-Cyclohexylhydroxyacetic acid; (R)-(-)-Hexahydromandelic acid; (R)-(-)-环己基羟基乙酸; (R)-(-)-六氢扁桃酸

Database IDs

• CAS Number: 53585-93-6
• MDL Number: MFCD00009824
• Beilstein Number: 3196809
• PubChem SID: 24874489; 24858168; 162245062
• PubChem CID: 819914

CALCULATED PROPERTIES

• Acid pKa: 4.1968994
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.035974357
• LogD (pH = 7.4): -1.749918
• Log P: 1.2856458
• Molar Refractivity: 39.8362 cm^3
• Polarizability: 15.915163 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-129 °C(lit.); 127-130 °C
• Optical Rotation: [α]18/D -23°, c = 1 in acetic acid; [α]20/D -23±1°, c = 1% in acetic acid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (sum of enantiomers, HPLC); 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Linear Formula: C6H11CH(OH)CO2H

DETAILS

Sigma Aldrich - 301140

Packaging
1 g in glass bottle

Sigma Aldrich - 52550

Other Notes
Chiral auxiliary substance for enantioselective aldol-condensations via boron enolates1,2,3,4