| Identification | More | [Name]
Phenoxyacetic acid | [CAS]
122-59-8 | [Synonyms]
AKOS BBS-00003724
FEMA 2872
Glycolic acid phenyl ether
O-PHENYLGLYCOLIC ACID
PHENOXYACETIC ACID
PHENOXYETHANOIC ACID
PHENYL ETHER GLYCOLIC ACID
PHENYLIUM(R)
PHENYLIUM(TM)
PHENYLOXYL ACETIC ACID
RARECHEM AL BO 0458
Acide phenoxyacetique
acidephenoxyacetique
Glycollic acid phenyl ether
glycollicacidphenylether
phenoxyacetic
Phenxoyacetic acid
PHENOXYACETIC ACID FREE ACID
PHENOXYACETIC ACID 98+%
Phenoxyacetic acid, purum | [EINECS(EC#)]
204-556-7 | [Molecular Formula]
C8H8O3 | [MDL Number]
MFCD00004296 | [Molecular Weight]
152.15 | [MOL File]
122-59-8.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white powder | [Melting point ]
98-100 °C (lit.) | [Boiling point ]
285 °C
| [density ]
1.2143 (rough estimate) | [FEMA ]
2872 | [refractive index ]
1.4447 (estimate) | [Fp ]
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 | [Stability:]
Stable. Substances to be avoided include strong bases, strong oxidizing agents. Combustible. | [Odor Type]
honey | [Water Solubility ]
0.1-0.5 g/100 mL at 17 ºC | [JECFA Number]
1026 | [Merck ]
14,7254 | [BRN ]
907949 | [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]
122-59-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [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 |
| Hazard Information | Back Directory | [General Description]
Light tan powder or white solid. | [Reactivity Profile]
PHENOXYACETIC ACID(122-59-8) reacts exothermically with all bases, both organic (for example, the amines) and inorganic. | [Air & Water Reactions]
Slightly soluble in water. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: This compound is a mild skin irritant. | [Fire Hazard]
Flash point data for this chemical are not available; however PHENOXYACETIC ACID is probably combustible. | [Chemical Properties]
off-white powder | [Chemical Properties]
Phenoxyacetic acid has a sour, sweet odor and a honey-like taste. | [Occurrence]
Reported found in cocoa beans | [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(122-59-8) 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.
| [Preparation]
By reacting phenol and monochloroacetic acid. | [Synthesis Reference(s)]
Synthetic Communications, 16, p. 479, 1986 DOI: 10.1080/00397918608057726 | [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%.
 | [storage]
Store at -20°C | [Purification Methods]
Crystallise the acid from water or aqueous EtOH. [Beilstein 6 IV 634.] |
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