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N-Aminophthalimide, 94%, Thermo Scientific Chemicals
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Catalog number A19914.18
also known as A19914-18
Price (USD)/ Each
340.65
Online exclusive
378.00 Save 37.35 (10%)
-
Quantity:
50 g
Price (USD)/ Each
340.65
Online exclusive
378.00 Save 37.35 (10%)
N-Aminophthalimide, 94%, Thermo Scientific Chemicals
Catalog numberA19914.18
Price (USD)/ Each
340.65
Online exclusive
378.00 Save 37.35 (10%)
-
Chemical Identifiers
CAS1875-48-5
IUPAC Name2-amino-2,3-dihydro-1H-isoindole-1,3-dione
Molecular FormulaC8H6N2O2
InChI KeyKSILMCDYDAKOJD-UHFFFAOYSA-N
SMILESNN1C(=O)C2=CC=CC=C2C1=O
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Specification SheetIt is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
It is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines
Solubility
Solubility in hot methanol almost transparent.
Notes
Store away from oxidizing agents, strong bases and heat. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Keep it refrigerated.
It is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines
Solubility
Solubility in hot methanol almost transparent.
Notes
Store away from oxidizing agents, strong bases and heat. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Keep it refrigerated.
RUO – Research Use Only
General References:
- Kung-Shou Yang.; Kwunmin Chen. Enantioselective aziridination of alkenes with N-aminophthalimide in the presence of lead tetraacetate-mediated chiral ligand.Org Lett.2002,4(7), 1107-1109.
- David J. Anderson, et al. Reactive intermediates. Part XXII. Formation of 2H-azirines by oxidation of N-aminophthalimide in the presence of alkynes.J. Chem. Soc., Perkin Trans. 1.1973,550-555.
- 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).