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

• ChemBase ID: 149429
• Molecular Formular: C6H6O5
• Molecular Mass: 158.10884
• Monoisotopic Mass: 158.02152329
• SMILES: CC(=O)O[C@@H]1CC(=O)OC1=O
• Canonical SMILES: CC(=O)O[C@@H]1CC(=O)OC1=O
• InChI: InChI=1S/C6H6O5/c1-3(7)10-4-2-5(8)11-6(4)9/h4H,2H2,1H3/t4-/m1/s1
• InChIKey: SSWJHSASZZAIAU-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2,5-dioxooxolan-3-yl acetate
• IUPAC Traditional name: (3R)-2,5-dioxooxolan-3-yl acetate
• Synonyms: (R)-3-Acetoxy-dihydro-2,5-furandione; O-Acetyl-D-malic anhydride; (R)-(+)-2-Acetoxysuccinic anhydride; D-O-Acetylmalic anhydride; (3R)-3-(Acetyloxy)dihydro-2,5-furandione; (+)-Acetoxysuccinic Anhydride; (R)-(+)-2-Acetoxysuccinic Anhydride; (R)-Acetoxysuccinic Anhydride; (R)-2-O-Acetylmalic Anhydride; (3S)-3-(Acetyloxy)dihydro-2,5-furandione; (-)-Acetoxysuccinic Anhydride; (S)-(-)-2-Acetoxysuccinic Anhydride; (S)-Acetoxysuccinic Anhydride; (S)-2-O-Acetylmalic Anhydride; (R)-3-乙酰氧基二氢-2,5-呋喃二酮; O-乙酰基-D-苹果酸酐; (R)-(+)-2-乙酰氧基琥珀酸酐; (R)-(+)-2-乙酰氧基丁二酸酐

Database IDs

• CAS Number: 79814-40-7; 59025-03-5
• MDL Number: MFCD00145214
• Beilstein Number: 130824
• PubChem SID: 24867669; 162243594
• PubChem CID: 9815264

CALCULATED PROPERTIES

• Acid pKa: 17.33598
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.30501068
• LogD (pH = 7.4): -0.30501068
• Log P: -0.538344
• Molar Refractivity: 30.8213 cm^3
• Polarizability: 12.925526 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMF; Ethyl Acetate
• Apperance: Powder; White Crystalline Solid
• Melting Point: 53-54°C; 56-58 °C(lit.); 56-58°C
• Optical Rotation: [α]20/D +27°, c = 1 in chloroform

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 96%; 98%
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C6H6O5

DETAILS

Sigma Aldrich - 441570

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - A185865

Used as intermediates for detergents via O-acetylmalic acid amides. Regioselective ring opening of malic acid anhydrides by carbon nucleophiles.

Toronto Research Chemicals - A185870

Used as intermediates for detergents via O-acetylmalic acid amides. Regioselective ring opening of malic acid anhydrides by carbon nucleophiles.

REFERENCES

• Clutterbuck, P., et al.: Biochem. J., 29, 300 (1935)
• Birkinshaw, J., et al.: J. Biochem., 74, 369 (1935)
• Sato, M., et al.: Chem. Pharm. Bull., 38, 94 (1935)
• Clutterbuck, P., et al.: Biochem. J., 29, 300 (1935)
• Birkinshaw, J., et al.: J. Biochem., 74, 369 (1935)
• Sato, M., et al.: Chem. Pharm. Bull., 38, 94 (1935)