2-amino-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 85712
• Molecular Formular: C8H6N2O2
• Molecular Mass: 162.14544
• Monoisotopic Mass: 162.04292744
• SMILES: N1(C(=O)c2c(cccc2)C1=O)N
• Canonical SMILES: NN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C8H6N2O2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H,9H2
• InChIKey: KSILMCDYDAKOJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-aminoisoindole-1,3-dione
• Synonyms: N,N-Phthaloylhydrazine, unsym.; N-Aminophthalimide; 2-aminoisoindoline-1,3-dione; 氨基邻苯二甲胺，不对称; N-氨基邻苯二甲酰亚胺

Database IDs

• CAS Number: 1875-48-5
• EC Number: 217-505-9
• MDL Number: MFCD00005895
• Beilstein Number: 383756
• PubChem SID: 24850729; 162072828
• PubChem CID: 74645

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.39687458
• LogD (pH = 7.4): 0.39694643
• Log P: 0.39694735
• Molar Refractivity: 43.7989 cm^3
• Polarizability: 15.594562 Å^3
• Polar Surface Area: 63.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200-202 °C(lit.); ca 195°C dec.

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/37/38-42/43
• Safety Statements: 22-26-36/37-45; 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~90% (HPLC); 90%; 94%; 97%
• Grade: technical; technical grade
• Empirical Formula (Hill Notation): C8H6N2O2

DETAILS

Sigma Aldrich - 178314

Other Notes
Remainder phthalhydrazide
Packaging
25 g in poly bottle
5 g in glass bottle
Application
Employed in the aziridination of chiral N-enoyl sultams.1

Sigma Aldrich - 09251

Analysis Note
typical IR Band 1715 and 1776 cm-1

REFERENCES

• May be oxidized with lead(IV) acetate to "phthalimidonitrene", which adds to alkenes to give aziridines. The phthalimido group can be cleaved with hydrazine hydrate: J. Chem. Soc. (C), 576 (1970); J. Am. Chem. Soc., 92, 1784 (1970); Helv. Chim. Acta,55, 1276 (1972); Org. Synth. Coll., 6, 56 (1988). Addition to cyclopentadienes leads to substituted pyridines after ring-opening with base: Heterocycles, 22, 1369 (1984). Addition to the (racemic) acrylic ester below shows an extremely high facial selectivity, adding to the less hindered side (290:1): Helv. Chim. Acta, 72, 1095 (1989).
  
• Aziridination has also been achieved in high yield by electrochemical oxidation: J. Am. Chem. Soc., 124, 530 (2002).