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85-41-6 - Phthalimide, 99% - Benzene-1,2-dicarboxylic acid imide - Isoindole-1,3-dione - A12584 - Alfa Aesar

A12584 Phthalimide, 99%

CAS Number
85-41-6
Synonyms
Benzene-1,2-dicarboxylic acid imide
Isoindole-1,3-dione

Size Price ($) Quantity Availability
500g 29.56
2500g 72.10
10000g 187.93
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Phthalimide, 99%

MDL
MFCD00005881
EINECS
201-603-3

Chemical Properties

Formula
C8H5NO2
Formula Weight
147.14
Melting point
232-236°
Boiling Point
366°
Flash Point
165°(329°F)
Density
1.21
Solubility
Slightly soluble in water. Soluble in aqueous alkali hydroxides

Applications

Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. . It is used as a precursor to other organic compounds as a masked source of ammonia.

Notes

Store at room temperature. Ensure good ventilation.

Literature References

John C. Sheehan.; William A. Bolhofer. An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides. J. Am. Chem. Soc. 1950, 72 (2), 2786-2788.

Lı?dia M Lima.; Paulo Castro.; Alexandre L Machado.; Carlos Alberto M Fraga.; Claire Lugnier.; Vera Lúcia Gonçalves de Moraes.; Eliezer J Barreiro. Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Bioorg. Med. Chem.. 2002, 10 (9),3067-3073.

For use in the Gabriel synthesis of primary amines, see: Potassium phthalimide, A11134. For an example of N-alkylation in the presence of K2CO3, see: Org. Synth. Coll., 2, 83 (1943). The N-alkylation by alkyl halides can be effected using KF, RbF or CsF as base; NaF and LiF are ineffective: J. Am. Chem. Soc., 99, 498 (1977).

The direct conversion of alcohols to N-alkylphthalimides and hence to amines can be effected in the presence of the Mitsunobu reagent: Org. Synth. Coll., 7, 501 (1990):

Other References

Merck
14,7373
Beilstein
118522
Harmonized Tariff Code
2925.19
TSCA
Yes
RTECS
TI3920000

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