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A19914 N-Aminophthalimide, 94%

CAS Number
1875-48-5
Synonyms

Stock No. Size Price ($) Quantity Availability
A19914-06 5g 43.30
A19914-09 10g 70.40
A19914-18 50g 296.00
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N-Aminophthalimide, 94%

MDL
MFCD00005895
EINECS
217-505-9

Chemical Properties

Formula
C8H6N2O2
Formula Weight
162.15
Melting point
ca 195° dec.
Storage & Sensitivity
Keep Cold.
Solubility
Solubility in hot methanol almost transparent.

Applications

It is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines

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.

Literature 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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
383756
Harmonized Tariff Code
2933.99
TSCA
No

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