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

• ChemBase ID: 88147
• Molecular Formular: C6H12O3
• Molecular Mass: 132.15768
• Monoisotopic Mass: 132.07864424
• SMILES: O1C(C)(C)OC[C@@H]1CO
• 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-/m0/s1
• InChIKey: RNVYQYLELCKWAN-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• IUPAC Traditional name: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• Synonyms: D-(+)-Solketal; (S)-(+)-1,2-Isopropylideneglycerol; 1,2-Isopropylidene-sn-glycerol; D-1,2-O-isopropylidene-sn-glycerol; (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol; D-α,β-Isopropylideneglycerol; (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol; 1,2-Isopropylidene-sn-glycerol; (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol; (S)-(+)-1,2-Isopropylideneglycerol, [(4S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol; (S)-Solketal; (4S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane 98%; (S)-(+)-2,3-O-Isopropylideneglycerol; [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol; (S)-(+)-1,2-Isopropylideneglycerol; (S)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醇; D-α,β-异亚丙基甘油; D-(+)-丙酮缩甘油; (S)-(+)-1,2-异亚丙基甘油; 1,2-异亚丙基-sn-甘油; (S)-(+)-2,3-异亚丙基甘油

Database IDs

• CAS Number: 22323-82-6
• EC Number: 244-910-8
• MDL Number: MFCD00063239
• Beilstein Number: 80118
• Merck Index: 145213
• PubChem SID: 24881509; 162075179; 24854267
• PubChem CID: 736057

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: 75-78 °C/12 mmHg; 82-83 °C/14 mmHg(lit.); 82-83°C/14mm; 82-83°C/14mm
• Flash Point: 194 °F; 80°C; 80°C(176°F); 90 °C
• Density: 1.066; 1.066 g/mL at 20 °C; 1.07; 1.07 g/mL at 25 °C(lit.)
• Refractive Index: 1.4350; n20/D 1.434; n20/D 1.434(lit.)
• Optical Rotation: [α]/D +13.5±1°, neat; [α]20/D +13.5°, neat; +11.5 (c=5 in methanol)
• Hydrophobicity(logP): 0.252

Safety Information

• Storage Warning: Irritant/Keep Cold
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95%; 97%; 98%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C6H12O3

DETAILS

Sigma Aldrich - 237744

Application
Used in a synthesis of a chiral allylic triol via extrusion of SO2 from an α,β-epoxysulfone.1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 59445

Other Notes
Key intermediate in the synthesis of enantiomerically pure compounds, EPC, review1; Preparation of glycerides2,3,4,5