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

• ChemBase ID: 118994
• Molecular Formular: C6H12O3
• Molecular Mass: 132.15768
• Monoisotopic Mass: 132.07864424
• SMILES: C1(O[C@@H](CO1)CO)(C)C
• Canonical SMILES: OC[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m1/s1
• InChIKey: RNVYQYLELCKWAN-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• IUPAC Traditional name: [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• Synonyms: (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol; 2,3-Isopropylidene-sn-glycerol; L-α,β-Isopropylideneglycerol; L-2,3-O-isopropylidene-sn-glycerol; (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol; (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol; 2,3-Isopropylidene-sn-glycerol; (R)-(-)-2,3-O-Isopropylideneglycerol; 2,3-异亚丙基-sn-甘油; L-α,β-异亚丙基甘油; L-2,3-O-异亚丙基-sn-甘油; (R)-(-)-甘油醇缩丙酮; (R)-(-)-2,2-二甲基-1,3-二氧戊环-4-甲醇; 2,3-异亚丙基-sn-甘油; (R)-(-)-2,3-O-异亚丙基甘油

Database IDs

• CAS Number: 14347-78-5
• MDL Number: MFCD00003213
• Beilstein Number: 80117
• Merck Index: 145213
• PubChem SID: 24854331; 162107372
• PubChem CID: 736056

CALCULATED PROPERTIES

• Acid pKa: 14.596533
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.13658941
• LogD (pH = 7.4): -0.13658944
• Log P: -0.13658941
• Molar Refractivity: 32.7231 cm^3
• Polarizability: 13.110614 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 72-73 °C/8 mmHg(lit.); 75-78 °C/12 mmHg; 82-83°C/14mm
• Flash Point: 174.2 °F; 79 °C; 80°C(176°F)
• Density: 1.062 g/mL at 25 °C(lit.); 1.064 g/mL at 20 °C(lit.); 1.066
• Refractive Index: 1.4350; n20/D 1.434; n20/D 1.434(lit.)
• Optical Rotation: [α]/D -13.5±1°, neat; [α]20/D -13.7°, neat; -11.5 (c=5 in methanol)

Safety Information

• RTECS: JI0400000
• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); 96%; 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C6H12O3

DETAILS

Sigma Aldrich - 241806

Application
Both (R)- and (S)-forms are chiral synthons used in the preparation of tetraoxaspiroundecanes,1 diglycerides,2 and glyceryl phosphates.3
Used in a new, efficient route to spiropyrans.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 59446

Other Notes
Important key intermediate for the synthesis of GABOB, glycerides and many other compounds1; See also 59445 D-enantiomer

REFERENCES

• Chiral starting material. Review: Tetrahedron, 42, 447 (1986).