(3R,4R)-4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate

• ChemBase ID: 145706
• Molecular Formular: C8H8O7
• Molecular Mass: 216.14492
• Monoisotopic Mass: 216.0270026
• SMILES: CC(=O)O[C@@H]1[C@H](C(=O)OC1=O)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C
• InChI: InChI=1S/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3/t5-,6-/m1/s1
• InChIKey: XAKITKDHDMPGPW-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate
• IUPAC Traditional name: (3R,4R)-4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate
• Synonyms: (+)-Diacetyl-L-tartaric anhydride; (+)-O,O′-Diacetyl-L-tartaric anhydride; (3R,4R)-2,5-Dioxotetrahydrofuran-3,4-diyl diacetate; (+)-二乙酰基-L-酒石酸酐; (+)-O,O′-二乙酰基-L-酒石酸酐

Database IDs

• CAS Number: 6283-74-5
• EC Number: 228-502-7
• MDL Number: MFCD00037918
• Beilstein Number: 87315
• PubChem SID: 162239909; 24862037
• PubChem CID: 513914

CALCULATED PROPERTIES

• Acid pKa: 13.77944
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.57904375
• LogD (pH = 7.4): -0.5790439
• Log P: -0.81237704
• Molar Refractivity: 41.311 cm^3
• Polarizability: 17.496927 Å^3
• Polar Surface Area: 95.97 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 130-135 °C; 130-135 °C(lit.)
• Optical Rotation: [α]20/D +59°, c = 6 in acetone; [α]20/D +60±2°, c = 6% in acetone

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (NT); 95+%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C8H8O7

DETAILS

Sigma Aldrich - 358924

Packaging
50 g in glass bottle

Sigma Aldrich - 31587

Other Notes
Reagent for the chiral derivatization of amino alcohols1,2; Preparation of tartramide chiral stationary phase for HPLC3; Partial kinetic resolution of alcohols4