(4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

• ChemBase ID: 147614
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CC1(OC[C@@H](O1)C=O)C
• Canonical SMILES: O=C[C@H]1COC(O1)(C)C
• InChI: InChI=1S/C6H10O3/c1-6(2)8-4-5(3-7)9-6/h3,5H,4H2,1-2H3/t5-/m0/s1
• InChIKey: YSGPYVWACGYQDJ-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• IUPAC Traditional name: (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• Synonyms: (R)-(+)-Glyceraldehyde acetonide; (R)-Isopropylideneglyceraldehyde; NSC 89869; (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde; (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛

Database IDs

• CAS Number: 15186-48-8
• MDL Number: MFCD00269682
• PubChem SID: 24868922; 162241801
• PubChem CID: 259712

CALCULATED PROPERTIES

• Acid pKa: 13.989225
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.025068877
• LogD (pH = 7.4): 0.025068767
• Log P: 0.02506888
• Molar Refractivity: 31.6651 cm^3
• Polarizability: 12.574146 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 139 °C(lit.)
• Flash Point: 143.6 °F; 62 °C
• Density: 1.045 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.454(lit.)
• Optical Rotation: [α]22/D +53.8°, c = 2 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C6H10O3

DETAILS

Sigma Aldrich - 454486

Packaging
500 mg in glass bottle
Application
Reactant involved in organic reactions including:
• Henry condensation reactions1
• Synthesis of highly functionalized chiral aziridines2
• Olefination of aldehydes3
• C-H oxidations4
• Aldol-type condensations5
• Synthesis of hydrophilic pyrazine dyes for use as exogenous fluorescent tracer agents6
• Hosomi-Sakurai reactions7