2-(oxiran-2-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 85247
• Molecular Formular: C11H9NO3
• Molecular Mass: 203.19406
• Monoisotopic Mass: 203.05824315
• SMILES: N1(C(=O)c2ccccc2C1=O)CC1OC1
• Canonical SMILES: O=C1N(CC2OC2)C(=O)c2c1cccc2
• InChI: InChI=1S/C11H9NO3/c13-10-8-3-1-2-4-9(8)11(14)12(10)5-7-6-15-7/h1-4,7H,5-6H2
• InChIKey: DUILGEYLVHGSEE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(oxiran-2-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: N-(2,3-epoxypropyl)phthalimide
• Synonyms: 2-Amino-2-deoxy-D-gluconic Acid; D-Glucosamic Acid; Glucosaminic acid; NSC 37779; NSC 404265; D-Glucosaminic Acid; 2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione; N-Glycidylphthalimide; N-(2,3-Epoxypropyl)phthalimide; 2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione; 2-(2-Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione; N-(2,3-Epoxypropyl)phthalimide; 2,3-Epoxypropylphthalimide; 2-(Phthalimidomethyl)oxirane; NSC 7244; N-Glycidyl Phthalimide; N-环氧丙基邻苯二甲酰亚胺; N-(2,3-环氧丙基)邻苯二甲酰亚胺

Database IDs

• CAS Number: 3646-68-2; 5455-98-1
• EC Number: 226-710-2
• MDL Number: MFCD00005896
• Beilstein Number: 171277
• PubChem SID: 162072363; 24868838; 24883316
• PubChem CID: 21601

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.75836575
• LogD (pH = 7.4): 0.75836575
• Log P: 0.75836575
• Molar Refractivity: 52.9562 cm^3
• Polarizability: 19.67128 Å^3
• Polar Surface Area: 49.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: White Solid; White to Off-White Solid
• Melting Point: >200°C (dec.); 92-98 °C(lit.); 98 - 100°C
• Hydrophobicity(logP): 0.958

Safety Information

• Storage Condition: Refrigerator
• RTECS: TI4950000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; ≥95.0% (GC); 90%; 95%
• Empirical Formula (Hill Notation): C11H9NO3

DETAILS

Sigma Aldrich - 644110

Packaging
10 g in glass bottle

Toronto Research Chemicals - G523000

A useful starting material for the synthesis of aldonic acids containing a free carboxyl group and having all hydroxyl functions esterified with a simple carboxylic acid are well established deriviatives.

Toronto Research Chemicals - G615995

Reagent used for the simultaneous preparation of a primary amine and secondary alcohol.

REFERENCES

• Major, R.T., et al.: J.A.C.S., 58, 2474 (1936)
• Hurd, C.D., et al.: J.A.C.S., 60, 235 (1936)
• Wolfrom, M., et al.: J.A.C.S., 61, 574 (1939)
• Carruthers, N., et al.: Bioorg. Med. Chem. Lett., 8, 3059 (1998)
• Nasreen, A., et al.: Res. J. Chem. Environ., 4, 63 (1998)