Potassium phthalimide

Potassium phthalimide
Identifiers
CAS Number	1074-82-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	10627162 ;
ECHA InfoCard	100.012.770
PubChem CID	3356745;
UNII	X6KKA27DIL ;
CompTox Dashboard (EPA)	DTXSID5027358 ;
	InChI InChI=1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1 Key: FYRHIOVKTDQVFC-UHFFFAOYSA-N ; InChI=1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1 Key: FYRHIOVKTDQVFC-UHFFFAOYAD; Key: FYRHIOVKTDQVFC-UHFFFAOYSA-N; InChI=1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1/p-1;
	SMILES C1=CC=C2C(=C1)C(=O)[N-]C2=O.[K+];
Properties
Chemical formula	C8H4KNO2
Molar mass	185.221 g/mol
Appearance	Light yellow solid
Melting point	> 300 °C (572 °F; 573 K)
Solubility in water	Soluble in water
Hazards
NFPA 704 (fire diamond)	2 1 0
Related compounds
Related compounds	Phthalimide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Potassium phthalimide is an organic compound with the formula C₆H₄(CO)₂NK. It is the potassium salt of phthalimide, and usually presents as fluffy, very pale yellow crystals. It can be prepared by combining phthalimide and potassium hydroxide.^[1]:

This compound is a commercially available reagent used in the Gabriel synthesis of amines. It is a precursor to anthranilic acid, although sodium phthalimide is a more typical precursor.^[2]

Structure

The structure of solid potassium phthalimide has been determined by X-ray crystallography. It is a salt, the K+ centers being bound to oxygen and nitrogen ligands.^[3]

References

↑ P. L. Salzberg and J. V. Supniewski (1927). "β-Bromoethylphthalimide". Organic Syntheses. 7: 8. doi:10.15227/orgsyn.007.0008.
↑ Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_555. ISBN 3527306730..
↑ Nagel, N.; Bock, H.; Bats, J. W. (1996). "Potassium Phthalimide". Acta Crystallographica Section C Crystal Structure Communications. 52 (6): 1344–1346. doi:10.1107/S0108270196002387.

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[1] P. L. Salzberg and J. V. Supniewski (1927). "β-Bromoethylphthalimide". Organic Syntheses. 7: 8. doi:10.15227/orgsyn.007.0008.

[2] Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_555. ISBN 3527306730..

[3] Nagel, N.; Bock, H.; Bats, J. W. (1996). "Potassium Phthalimide". Acta Crystallographica Section C Crystal Structure Communications. 52 (6): 1344–1346. doi:10.1107/S0108270196002387.

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