(2S,5S)-hexane-2,5-diol

• ChemBase ID: 148795
• Molecular Formular: C6H14O2
• Molecular Mass: 118.17416
• Monoisotopic Mass: 118.09937969
• SMILES: C[C@@H](CC[C@H](C)O)O
• Canonical SMILES: C[C@@H](CC[C@@H](O)C)O
• InChI: InChI=1S/C6H14O2/c1-5(7)3-4-6(2)8/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1
• InChIKey: OHMBHFSEKCCCBW-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S)-hexane-2,5-diol
• IUPAC Traditional name: (2S,5S)-hexane-2,5-diol
• Synonyms: (2S,5S)-2,5-Hexanediol; [S-(R*,R*)]-2,5-Hexanediol; 1,3,4,6-Tetradeoxy-L-threo-hexitol; (+)-2,5-Hexanediol; (2S,5S)-(+)-Hexanediol; (2S,5S)-Hexanediol; (S,S)-2,5-Hexanediol; (2S,5S)-2,5-Hexanediol; (2S,5S)-2,5-已二醇; (2S,5S)-2,5-己二醇

Database IDs

• CAS Number: 34338-96-0
• MDL Number: MFCD00082583
• Beilstein Number: 4652444
• PubChem SID: 24874657; 162242969; 24864681
• PubChem CID: 6950288

CALCULATED PROPERTIES

• Acid pKa: 15.358763
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.20179337
• LogD (pH = 7.4): 0.20179337
• Log P: 0.20179337
• Molar Refractivity: 32.9012 cm^3
• Polarizability: 13.0251875 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 50-53 °C(lit.); 50-53°C; 52-54 °C; 52-54°C
• Boiling Point: 212-215 °C(lit.); 212-215°C; 216-218°C
• Flash Point: 101°C(215°F); 102 °C; 215.6 °F
• Optical Rotation: [α]20/D +34.5°, c = 9 in chloroform; [α]20/D +35±2°, c = 9% in chloroform

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 99%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: CH3CH(OH)CH2CH2CH(OH)CH3

DETAILS

Sigma Aldrich - 396729

Application
Used in the synthesis of phospholanes.1 A building block in the synthesis of trans-2,5-dimethylpyrrolidine.2 C2 symmetric chiral diol with versatile applications as a chiral auxiliary,3,4 building block,5,6,7 and chiral ligand.8,9
Packaging
1 g in glass bottle

Sigma Aldrich - 52793

Other Notes
Chiral auxiliary; acetals react diastereoselectively with cuprates1; Starting material for the preparation of (R,R)-2,5-dimethylpyrrolidine2

Toronto Research Chemicals - H292150

Used in the synthesis of new phospholanes. Reagent used for asymmetric syntheses.

REFERENCES

• Uppenberg, J., et al.: Biochemistry, 34, 16838 (1995)
• Mezzetti, A., et al.: Chem. Biol., 12, 427 (1995)
• Martin-Matute, B., et al.: Chem. Eur. J., 12, 6053 (1995)