Salicylic acid phenyl ester

Structural formula
General
Surname	Salicylic acid phenyl ester
other names	Phenyl salicylate; Salol; 2-Hydroxybenzoic acid phenyl ester; PHENYL SALICYLATE ( INCI ) ;
Molecular formula	C 13 H 10 O 3
Brief description	white solid
External identifiers / databases
EC number	204-259-2
ECHA InfoCard	100.003.873
PubChem	8361
ChemSpider	8058
DrugBank	DB11071
Wikidata	Q421259
properties
Molar mass	214.22 g mol −1
Physical state	firmly
Melting point	41-43 ° C
boiling point	172–173 ° C (16 h Pa )
solubility	bad in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Salicylic acid phenyl ester or phenyl salicylate is the phenyl ester of salicylic acid .

presentation

Phenyl salicylate can be prepared by reaction of Salicylsäurechlorid with phenol can be produced.

properties

Phenyl salicylate is a colorless, crystalline powder that has a slightly aromatic odor and is only very slightly soluble in water, but more soluble in benzene , chloroform , ethanol and ether .

The bromination of phenyl salicylate with elemental bromine in glacial acetic acid initially leads to the 5-bromo derivative. The 3,5-dibromo derivative is formed when 2 moles of bromine are used.

use

Phenyl salicylate has an antiseptic and anti-rheumatic effect and is also used as UV -protection for the skin and for plastics use. It was introduced into therapy in 1886 as Salol ^® ; The main purpose was to disinfect the urinary tract .

Individual evidence

↑ Entry on PHENYL SALICYLATE in the CosIng database of the EU Commission, accessed on May 22, 2020.
↑ ^a ^b ^c ^d ^e data sheet Phenyl salicylate from Sigma-Aldrich , accessed on April 22, 2011 and January 17, 2012 ( PDF ).
↑ Data sheet salicylic acid phenyl ester from Acros, accessed on April 2, 2010.
↑ Günter Jeromin: "Organic Chemistry: A Practice-Related Textbook", Harri Deutsch Verlag, 2006, p. 294, ISBN 978-3-8171-1732-1 . ( limited preview in Google Book search).
↑ P. Kauschke: "About the action of bromine on salicylic and benzoic phenyl, benzoic o-, m- and p-cresyl, and benzoic guaiacol" in J. Prakt. Chem. 1895 , 51 , p. 210ff.
↑ Entry on salicylic acid esters. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
^ Harry Auterhoff , Textbook of Pharmaceutical Chemistry, Wissenschaftliche Verlagsgesellschaft Stuttgart, 1968.

[CosIng-1] Entry on PHENYL SALICYLATE in the CosIng database of the EU Commission, accessed on May 22, 2020.

[SIGMA-2] ↑ ^a ^b ^c ^d ^e data sheet Phenyl salicylate from Sigma-Aldrich , accessed on April 22, 2011 and January 17, 2012 ( PDF ).

[3] Data sheet salicylic acid phenyl ester from Acros, accessed on April 2, 2010.

[Jeromin-4] Günter Jeromin: "Organic Chemistry: A Practice-Related Textbook", Harri Deutsch Verlag, 2006, p. 294, ISBN 978-3-8171-1732-1 . ( limited preview in Google Book search).

[Kauschke-5] P. Kauschke: "About the action of bromine on salicylic and benzoic phenyl, benzoic o-, m- and p-cresyl, and benzoic guaiacol" in J. Prakt. Chem. 1895 , 51 , p. 210ff.

[6] Entry on salicylic acid esters. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[7] Harry Auterhoff , Textbook of Pharmaceutical Chemistry, Wissenschaftliche Verlagsgesellschaft Stuttgart, 1968.