methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

• ChemBase ID: 145482
• Molecular Formular: C7H12O4
• Molecular Mass: 160.16778
• Monoisotopic Mass: 160.07355886
• SMILES: CC1(OC[C@H](O1)C(=O)OC)C
• Canonical SMILES: COC(=O)[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1
• InChIKey: DOWWCCDWPKGNGX-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• IUPAC Traditional name: methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• Synonyms: α,β-Isopropylidene-L-glyceric acid methyl ester; Methyl α,β-isopropylidene-L-glycerate; Methyl 2,3-O-isopropylidene-L-glycerate; (-)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate; (S)-methyl2,2-dimethyl-1,3-dioxolane-4-carboxylate; (S)-Methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate; α,β-异亚丙基-L-甘油酸甲酯; 2,3-O-异亚丙基-L-甘油酸甲酯; 甲基α,β-异亚丙基-L-甘油酸酯; (S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯

Database IDs

• CAS Number: 60456-21-5
• MDL Number: MFCD00066526
• Beilstein Number: 4292352
• PubChem SID: 162239687; 24855396; 24881513
• PubChem CID: 853165

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.32957917
• LogD (pH = 7.4): 0.32957917
• Log P: 0.32957917
• Molar Refractivity: 37.3596 cm^3
• Polarizability: 15.146889 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 84-86 °C/15 mmHg(lit.)
• Flash Point: 172.4 °F; 78 °C
• Density: 1.106 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.425(lit.); n20/D 1.426
• Optical Rotation: [α]20/D -10.5±1°, neat; [α]20/D -8.5°, c = 1.5 in acetone

Safety Information

• German water hazard class: 3
• 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: ≥97.0% (sum of enantiomers, GC); 95+%; 96%; 97%
• Grade: purum
• Optical Purity: ee: ≥96.0% (GLC); enantiomeric ratio: ≥98.0:2.0 (GC)
• Empirical Formula (Hill Notation): C7H12O4

DETAILS

Sigma Aldrich - 254606

Application
Chiral building block used to make the key tetrahydrofuran subunit of (-)-gymnodimine a marine agal toxin.1
Packaging
5 g in glass bottle