[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

• ChemBase ID: 148736
• Molecular Formular: C7H14O4
• Molecular Mass: 162.18366
• Monoisotopic Mass: 162.08920893
• SMILES: CC1(O[C@@H]([C@H](O1)CO)CO)C
• Canonical SMILES: OC[C@H]1OC(O[C@@H]1CO)(C)C
• InChI: InChI=1S/C7H14O4/c1-7(2)10-5(3-8)6(4-9)11-7/h5-6,8-9H,3-4H2,1-2H3/t5-,6-/m1/s1
• InChIKey: INVRLGIKFANLFP-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• IUPAC Traditional name: [(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• Synonyms: (4R,5R)-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol; (4R,5R)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane; (-)-2,3-O-Isopropylidene-D-threitol; (-)-2,3-O-Isopropylidene-D-threitol; (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol; (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol; (4R,5R)-(-)-2,2-二甲基-1,3-二氧戊环-4,5-二甲醇; (4R,5R)-4,5-双(羟甲基)-2,2-二甲基-1,3-二氧戊环; (-)-2,3-O-异亚丙基-D-苏糖醇; (-)-2,3-O-异亚丙基-D-苏糖醇; (-)-2,3-O-亚异丙基-D-苏力糖醇; (4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二甲醇; 2,3-O-异亚丙基-D-苏醇

Database IDs

• CAS Number: 73346-74-4
• EC Number: 277-391-1
• MDL Number: MFCD00009761
• Beilstein Number: 1798
• PubChem SID: 24854482; 162242911; 24881574
• PubChem CID: 785244

CALCULATED PROPERTIES

• Acid pKa: 14.281928
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.7669243
• LogD (pH = 7.4): -0.7669244
• Log P: -0.7669243
• Molar Refractivity: 38.6856 cm^3
• Polarizability: 15.614053 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 45-49°C; 46-50 °C; 48-51 °C(lit.)
• Boiling Point: 88-90°C/0.05mm; 91-93 °C/0.01 mmHg(lit.)
• Flash Point: >110°C(230°F)
• Optical Rotation: [α]20/D -3.0±0.5°, c = 5% in ethanol; [α]26/D -3.1°, c = 5 in chloroform; -4.5 (c=5 in ethanol)

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.5% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C7H14O4

DETAILS

Sigma Aldrich - 241415

Packaging
1 g in glass bottle

Sigma Aldrich - 59535

Other Notes
Chiral synthon ex tartaric acid used as chiral building block 1,2,3,4

REFERENCES

• Chiral intermediate: J. Am. Chem. Soc., 94, 6429 (1972).