Phenoxyacetic acid Chemical Properties

Melting point:

98-100 °C (lit.)

Boiling point:

285 °C

Density 

1.2143 (rough estimate)

refractive index 

1.4447 (estimate)

FEMA 

2872 | PHENOXYACETIC ACID

Flash point:

165 °C

storage temp. 

Store below +30°C.

solubility 

ethanol: soluble10%, clear, colorless

form 

Granular Powder, Granules, or Prills

pka

3.17(at 25℃)

color 

White

Odor

at 1.00 % in propylene glycol. sour sweet

Odor Type

honey

Water Solubility 

0.1-0.5 g/100 mL at 17 ºC

Merck 

14,7254

JECFA Number

1026

BRN 

907949

Stability:

Stable. Substances to be avoided include strong bases, strong oxidizing agents. Combustible.

InChIKey

LCPDWSOZIOUXRV-UHFFFAOYSA-N

LogP

1.34

CAS DataBase Reference

122-59-8(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, phenoxy-(122-59-8)

EPA Substance Registry System

Phenoxyacetic acid (122-59-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 3345 6.1/ PGIII

WGK Germany 

3

RTECS 

AJ2230000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29189090

Toxicity

LD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rabbit > 5000 mg/kg

MSDS

• Language:English Provider:Glycolic acid phenyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Phenoxyacetic acid Usage And Synthesis

Chemical Properties

Phenoxyacetic acid has a sour, sweet odor and a honey-like taste.

Occurrence

Reported found in cocoa beans

Uses

Phenoxyacetic acid is a flavoring ingredient.?Its photodegradation using titanium dioxide as photocatalyst has been studied. Selective separation of penicillin V from phenoxyacetic acid using liquid membranes consisting of 1,2-dichloroethane and Amberlite LA-2 as carrier has been studied.

Uses

Fungicide; keratin exfoliative (to relieve and to soften calluses, corns, and other hard skin surfaces; applied as plasters, pads or in liquids).

Definition

ChEBI: Phenoxyacetic acid is a monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes. It has a role as a human xenobiotic metabolite, an Aspergillus metabolite, a plant growth retardant and an allergen. It is a monocarboxylic acid and an aromatic ether. It is functionally related to a glycolic acid. It is a conjugate acid of a phenoxyacetate.

Synthesis Reference(s)

Synthetic Communications, 16, p. 479, 1986 DOI: 10.1080/00397918608057726

General Description

Light tan powder or white solid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Phenoxyacetic acid reacts exothermically with all bases, both organic (for example, the amines) and inorganic.

Health Hazard

ACUTE/CHRONIC HAZARDS: Phenoxyacetic acid is a mild skin irritant.

Fire Hazard

Flash point data for Phenoxyacetic acid are not available; however Phenoxyacetic acid is probably combustible.

Synthesis

A Schlenk tube was charged with aryl iodides (1) (1.0 mmol), glycolic acid (228 mg, 3.0 mmol), CuI (19.0 mg, 0.1 mmol), Cs2CO3 (1.95 g, 6.0 mmol), and DMSO/H2O (2 mL/1 mL). The mixture was stirred for 24 h at 120 ℃ under Ar. The reaction mixture was allowed to cool to room temperature, poured into 5 mL of water, and then acidified to pH = 1 with 2 N HCl solution. The aqueous phase was extracted twice with EtOAc, and the combined organic layer was washed with H2O and brine, dried over anhydrous MgSO4, and concentrated under vacuum. Purification of the crude product by column chromatography (dichloromethane/methanol) afforded the desired product Phenoxyacetic acid, white solid, yield 133 mg, 88%. 

Purification Methods

Crystallise the acid from water or aqueous EtOH. [Beilstein 6 IV 634.]

Phenoxyacetic acid(122-59-8)Related Product Information

• Glycolic acid
• Ethyl phenylacetate
• Ethyl 2-(Chlorosulfonyl)acetate
• Fluroxypyr
• PHENYL VALERATE
• Ethylbenzene
• Diphenyl ether
• Folic acid
• Stearic acid
• Phenyl salicylate
• Citric acid
• Hyaluronic acid
• 4-Hydroxyphenylacetic acid
• 2-Hydroxyphenylacetic acid
• Triclopyr
• 4-Chlorophenoxyacetic acid
• PHENYL RESIN
• Ascoric Acid
• Phenoxyacetic