2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

• ChemBase ID: 33076
• Molecular Formular: C10H7NO4
• Molecular Mass: 205.16688
• Monoisotopic Mass: 205.03750771
• SMILES: N1(C(=O)c2c(C1=O)cccc2)CC(=O)O
• Canonical SMILES: OC(=O)CN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C10H7NO4/c12-8(13)5-11-9(14)6-3-1-2-4-7(6)10(11)15/h1-4H,5H2,(H,12,13)
• InChIKey: WQINSVOOIJDOLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid
• IUPAC Traditional name: (1,3-dioxoisoindol-2-yl)acetic acid
• Synonyms: 1,3-Dihydro-1,3-dioxo-2h-isoindole-2-aceticacid; N-Phthaloylglycine; 1,3-Dioxo-2-isoindolineacetic acid; Phthalimidoacetic acid; N-Phthaloylglycine; N-Phthaloylglycine; (1,3-Dioxoisoindolin-2-yl)acetic acid; N-(Carboxymethyl)phthalimide; 2-(Carboxymethyl)-1,3-dioxoisoindoline; (1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetic acid 98%; (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid; (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-acetic acid; 1,3-二氧-2-异吲哚啉乙酸; 邻苯二甲酰甘氨酸; N-邻苯二甲酰甘氨酸; N-酞酰甘氨酸

Database IDs

• CAS Number: 4702-13-0
• EC Number: 225-177-3
• MDL Number: MFCD00005900
• Beilstein Number: 184174
• PubChem SID: 24887506; 24898488; 160996383
• PubChem CID: 20825

CALCULATED PROPERTIES

• Acid pKa: 2.9864202
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -2.0798545
• LogD (pH = 7.4): -3.0810993
• Log P: 0.3950824
• Molar Refractivity: 50.2961 cm^3
• Polarizability: 18.4634 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 193-196 °C; 193-196 °C(lit.); 193-196°C; 194-198°C
• Partition Coefficient: 0.576

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: NR3439000
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (T); 95+%; 97%; 98%; 98+%
• Grade: puriss.
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C10H7NO4

DETAILS

Sigma Aldrich - P40506

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 79850

Other Notes
Protected glycine. The acid chloride is employed in (2+2) ketene-imine-cycloadditions1

REFERENCES

• Starting material for chiral azetidinone synthesis: Org. Synth. Coll., 9, 13 (1998).