(2R,4R)-pentane-2,4-diol

• ChemBase ID: 145783
• Molecular Formular: C5H12O2
• Molecular Mass: 104.14758
• Monoisotopic Mass: 104.08372962
• SMILES: C[C@H](C[C@@H](C)O)O
• Canonical SMILES: C[C@H](C[C@H](O)C)O
• InChI: InChI=1S/C5H12O2/c1-4(6)3-5(2)7/h4-7H,3H2,1-2H3/t4-,5-/m1/s1
• InChIKey: GTCCGKPBSJZVRZ-RFZPGFLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-pentane-2,4-diol
• IUPAC Traditional name: (2R,4R)-pentane-2,4-diol
• Synonyms: (R,R)-(-)-2,4-Pentanediol; (R,R)-(-)-2,4-戊二醇

Database IDs

• CAS Number: 42075-32-1
• MDL Number: MFCD00063893
• Beilstein Number: 4290613
• PubChem SID: 162239985; 24887077; 24854603
• PubChem CID: 2723683

CALCULATED PROPERTIES

• Acid pKa: 15.279934
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.31556928
• LogD (pH = 7.4): -0.3155693
• Log P: -0.31556928
• Molar Refractivity: 28.2566 cm^3
• Polarizability: 11.190113 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 48-50 °C(lit.); 48-51 °C
• Boiling Point: 111-113 °C/19 mmHg(lit.)
• Flash Point: 101 °C; 213.8 °F
• Optical Rotation: [α]20/D -41±2°, c = 10% in chloroform; [α]21/D -40.4°, c = 10 in chloroform

Safety Information

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

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 99%
• Grade: purum
• Optical Purity: ee: 97% (GLC)
• Linear Formula: CH3CH(OH)CH2CH(OH)CH3

DETAILS

Sigma Aldrich - 243175

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application
Acetalization reagent for ketones1 and β-keto esters.2 Used in the synthesis of optically active polyesters.3 C2 symmetric chiral diol with versatile applications as a chiral auxiliary,4,5 building block,6,7,8 and chiral ligand.9,10

Sigma Aldrich - 76897

Other Notes
Chiral dioxane acetals of this diol react diastereoselectively1,2,3; Chiral derivatizing agent for carbonyls4