Phthalide

Structural formula
General
Surname	Phthalide
other names	3H -isobenzofuran-1-one; 1-phthalanone;
Molecular formula	C 8 H 6 O 2
Brief description	colorless to yellowish powder
External identifiers / databases
EC number	201-744-0
ECHA InfoCard	100.001.586
PubChem	6885
Wikidata	Q7188203
properties
Molar mass	134.14 g mol −1
Physical state	firmly
density	1.1613 g cm −3
Melting point	71 - 73 ° C
boiling point	290 ° C
solubility	slightly soluble in water (18.4 g l −1 at 25 ° C)
Refractive index	1.536 (99 ° C)
safety instructions
GHS labeling of hazardous substances
H and P phrases	H: 319
	P: 305-351-338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Phthalide is a chemical that is produced synthetically and also occurs as a secondary plant substance. The phthalide derivatives 3-butylphthalide and sedanolide are found in celery and lovage , for example .

Extraction and presentation

Phthalide can be obtained by reacting phthalimide with sodium hydroxide with an admixture of zinc and copper sulfate and then reacting the intermediate product with hydrogen chloride.

In general, phthalides can be obtained from 2-formyl aryl ketones in dimethyl sulfoxide (DMSO) either by a Cannizarro-Tischtschenko reaction under nucleophilic catalysis (NaCN) or under photochemical conditions .

use

Phthalide is a raw material for many other syntheses, e.g. B. from kresoxim-methyl and picoxystrobin . In 2013, the usability of phthalide in the Suzuki coupling was demonstrated for the first time .

Derivatives

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry for CAS no. 87-41-2 in the GESTIS substance database of the IFA , accessed on April 17, 2013(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-308.
↑ ^a ^b Phthalide data sheet from Sigma-Aldrich , accessed on April 17, 2013 ( PDF ).

^ Butyl Phthalide

↑ Textbook food chemistry and nutrition in the Google book search.

^ JH Gardner and CA Naylor jr .: Phthalide In: Organic Syntheses . 16, 1936, p. 71, doi : 10.15227 / orgsyn.016.0071 ; Coll. Vol. 2, 1943, p. 26 ( PDF ).

↑ DC Gerbino, D. Augner, N. Slavoy, H.-G. Schmalz: Phthalide synthesis . In: Org. Lett. , 2012, 14, 2338-2341.

↑ James McNulty, Kunal Keskar: Phthalide: a direct building block towards P, O and P, N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides. In: Organic & Biomolecular Chemistry. 11, 2013, p. 2404, doi : 10.1039 / C3OB40198G .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry for CAS no. 87-41-2 in the GESTIS substance database of the IFA , accessed on April 17, 2013(JavaScript required) .

[CRC90_3_308-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-308.

[Sigma-3] Phthalide data sheet from Sigma-Aldrich , accessed on April 17, 2013 ( PDF ).

[4] Butyl Phthalide

[5] Textbook food chemistry and nutrition in the Google book search.

[6] JH Gardner and CA Naylor jr .: Phthalide In: Organic Syntheses . 16, 1936, p. 71, doi : 10.15227 / orgsyn.016.0071 ; Coll. Vol. 2, 1943, p. 26 ( PDF ).

[organic-chemistry-7] DC Gerbino, D. Augner, N. Slavoy, H.-G. Schmalz: Phthalide synthesis . In: Org. Lett. , 2012, 14, 2338-2341.

[DOI10.1039/C3OB40198G-8] James McNulty, Kunal Keskar: Phthalide: a direct building block towards P, O and P, N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides. In: Organic & Biomolecular Chemistry. 11, 2013, p. 2404, doi : 10.1039 / C3OB40198G .