Phenoxyacetic acid

Structural formula
General
Surname	Phenoxyacetic acid
other names	2-phenoxyacetic acid ( IUPAC )
Molecular formula	C 8 H 8 O 3
Brief description	white to beige powder, needle-shaped crystals
External identifiers / databases
EC number	204-556-7
ECHA InfoCard	100.004.143
PubChem	19188
ChemSpider	18107
Wikidata	Q904253
properties
Molar mass	152.15 g mol −1
Physical state	firmly
Melting point	98-100 ° C
boiling point	285 ° C
pK s value	3.17 (25 ° C)
solubility	12 g l −1 in water; good in glacial acetic acid , ethanol and diethyl ether ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 302 + 352-304 + 340-305 + 351 + 338
Toxicological data	1500 mg kg −1 ( LD 50 , rat , oral ) ; 3750 mg kg −1 ( LD 50 , mouse , oral ) ; > 200 mg kg −1 ( LD 50 , rabbit , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenoxyacetic acid is an organic compound that smells like honey. It forms colorless, needle-shaped crystals that are difficult to dissolve in water and easily soluble in glacial acetic acid, alcohol and ether. The substance is a medium strong acid (pK _s = 3.17) and has a strong antiseptic.

presentation

Phenoxyacetic acid can be obtained from the reaction of phenol and chloroacetic acid with sodium hydroxide solution . The sodium hydroxide solution deprotonates the hydroxyl group of the phenol. The resulting phenolate now attacks nucleophilically on the β - carbon atom of chloroacetic acid, splitting off a chloride ion .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Data sheet phenoxyacetic acid (PDF) from Merck , accessed on December 26, 2019.
↑ ^a ^b Wissenschaft-Online-Lexika: Entry on phenoxyacetic acid in the Lexikon der Chemie , accessed September 6, 2008.
^ Entry on phenoxyacetic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Gigiena i Sanitariya. (HYSAAV) Vol. 46 (1), 1981, p. 25.
^ Food and Cosmetics Toxicology . Vol. 17, 1979, p. 887.
↑ P. Giacosa: Advantageous presentation of phenolglycolic acid and pyrogallol triglycolic acid , in: J. Prakt. Chem. , 1879 , 19 , pp. 396-399.

[Merck-1] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet phenoxyacetic acid (PDF) from Merck , accessed on December 26, 2019.

[woc-2] Wissenschaft-Online-Lexika: Entry on phenoxyacetic acid in the Lexikon der Chemie , accessed September 6, 2008.

[3] Entry on phenoxyacetic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] Gigiena i Sanitariya. (HYSAAV) Vol. 46 (1), 1981, p. 25.

[5] Food and Cosmetics Toxicology . Vol. 17, 1979, p. 887.

[6] P. Giacosa: Advantageous presentation of phenolglycolic acid and pyrogallol triglycolic acid , in: J. Prakt. Chem. , 1879 , 19 , pp. 396-399.