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22509-74-6 - N-(Ethoxycarbonyl)phthalimide, 97% - N-(Carbethoxy)phthalimide - Nefkens' Reagent - A14822 - Alfa Aesar

A14822 N-(Ethoxycarbonyl)phthalimide, 97%

CAS Number
22509-74-6
Synonyms
N-(Carbethoxy)phthalimide
Nefkens' Reagent

Size Price ($) Quantity Availability
25g 29.68
100g 113.40
500g 452.80
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N-(Ethoxycarbonyl)phthalimide, 97%

MDL
MFCD00005893
EINECS
245-048-5

Chemical Properties

Formula
C11H9NO4
Formula Weight
219.20
Melting point
78-84°
Solubility
Insoluble in water.

Applications

N-(Ethoxycarbonyl)phthalimide is used to protect amine functional groups. Reagent for the conversion of amines and amino acids to their phthaloyl derivatives under mild conditions

Notes

Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.

Literature References

Paul M. Worster.; Clifford C. Leznoff.; Colin R. McArthur. N-(Ethoxycarbonyl)phthalimide. An improved procedure. J. Org. Chem. 1980, 45, (1), 174-175.

M. Niyaz Khan. Suggested Improvement in the Ing-Manske Procedure and Gabriel Synthesis of Primary Amines:? Kinetic Study on Alkaline Hydrolysis of N-Phthaloylglycine and Acid Hydrolysis of N-(o-Carboxybenzoyl)glycine in Aqueous Organic Solvents. J. Org. Chem. 1980, 61, (23), 8063-8068.

Reagent for the conversion of amines and amino acids to their phthaloyl derivatives under mild conditions: Nature, 185, 309 (1960); J. Heterocycl. Chem., 29, 707 (1992). For improved procedures involving reaction of an aqueous solution of the Na salt of an amino acid with a solution of the reagent in ethyl acetate, see: Rec. Trav. Chim., 97, 260 (1978), or using triethylamine in THF giving excellent yields without racemization: Can. J. Chem., 60, 1836 (1982). See also Appendix 6.

Other References

Beilstein
196340
Harmonized Tariff Code
2925.19
TSCA
Yes
RTECS
NR3459500

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