Phthalimide

Structural formula
General
Surname	Phthalimide
other names	1,2-benzene dicarboximide
Molecular formula	C 8 H 5 NO 2
Brief description	white, crystalline powder or flakes
External identifiers / databases
EC number	201-603-3
ECHA InfoCard	100.001.458
PubChem	6809
Wikidata	Q412784
properties
Molar mass	147.13 g mol −1
Physical state	firmly
density	1.21 g cm −3 (20 ° C)
Melting point	238 ° C
boiling point	310 ° C
pK s value	8.3
solubility	very poor in water (0.6 g l −1 at 20 ° C), benzene and petroleum ether , poor in ethanol ; soluble in alkaline solutions and glacial acetic acid ;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phthalimide is a chemical compound with the molecular formula C ₈ H ₅ NO ₂ . The white, crystalline compound is the imide of phthalic acid .

Extraction and presentation

The phthalic acid imide is synthesized by reacting phthalic anhydride with ammonia .

properties

Under normal conditions, phthalimide is an air-insensitive solid that can oxidize under the action of light. Due to the electron-withdrawing (–M) effect of the two carbonyl groups, phthalimide has a pronounced NH acidity . The flash point is 150 ° C, the ignition temperature is> 500 ° C.

Usage and reactions

The imide group has an acidic reaction (pK _a = 8.3) and can easily be converted to potassium phthalimide with alcoholic potassium hydroxide solution .

Potassium phthalimide is a reagent for the synthesis of primary amines according to the principle of the Gabriel synthesis . Phthalimide is also required in pesticides (e.g. folpet ), dyes and as a raw material for anthranilic acid .

Individual evidence

↑ ^a ^b ^c ^d Entry on phthalimide. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
↑ ^a ^b ^c ^d ^e ^f Entry on phthalimide in the GESTIS substance database of the IFA , accessed on December 20, 2019(JavaScript required) .
^ ^A ^b ^c Hans Beyer and Wolfgang Walter : Organische Chemie , S. Hirzel Verlag, Stuttgart, 1984, page 521, ISBN 3-7776-0406-2 .
^ Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, p. 490, ISBN 3-342-00280-8 .

[roempp-1] Entry on phthalimide. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f Entry on phthalimide in the GESTIS substance database of the IFA , accessed on December 20, 2019(JavaScript required) .

[Beyer-3] A ^b ^c Hans Beyer and Wolfgang Walter : Organische Chemie , S. Hirzel Verlag, Stuttgart, 1984, page 521, ISBN 3-7776-0406-2 .

[Hauptmann-4] Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, p. 490, ISBN 3-342-00280-8 .