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122-59-8

Basic Information
CAS No.: 122-59-8
Name: Phenoxyacetic acid
Article Data: 195
Molecular Structure:
Molecular Structure of 122-59-8 (Phenoxyacetic acid)
Formula: C8H8O3
Molecular Weight: 152.15
Synonyms: A328 Phenoxyacetic acid;Aceticacid, phenoxy- (8CI,9CI);2-Phenoxyacetic acid;Glycolic acid phenyl ether;NSC9810;Phenoxyethanoic acid;
EINECS: 204-556-7
Density: 1.221 g/cm3
Melting Point: 98-100 °C(lit.)
Boiling Point: 285 °C at 760 mmHg
Flash Point: 115.1 °C
Solubility: water: 0.1-0.5 g/100 mL at 17 °C
Appearance: off-white powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-36-37/39
PSA: 46.53000
LogP: 1.15000
Synthetic route
79-11-8

chloroacetic acid

108-95-2

phenol

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With 18-crown-6 ether; trimethyldodecylammonium chloride; tetra-n-butylphosphonium chloride; sodium hydroxide In water for 3h; pH=12; Reagent/catalyst; Williamson Ether Synthesis; Reflux;99.2%
With sodium hydroxide In water at 60 - 80℃; for 2h;98.5%
With sodium hydroxide Irradiation;97%
621-88-5

phenoxyacetamide

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With potassium hydrogensulfate; water In methanol at 100℃; for 48h;100%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.5h; microwave irradiation;79%
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 1.5h; Hydrolysis;75%
3926-62-3

sodium monochloroacetic acid

108-95-2

phenol

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20 - 60℃;75%
Stage #1: phenol With sodium hydroxide In ethanol; water at 20℃; for 0.333333h;
Stage #2: sodium monochloroacetic acid In ethanol; water at 102℃; for 5h;
75%
With sodium hydroxide In ethanol; water for 1h; Reflux;70.2%
With sodium hydroxide In ethanol; water at 105℃; for 5h;67%
2555-49-9

phenoxyacetic acid ethyl ester

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 20℃; for 12h;95%
Stage #1: phenoxyacetic acid ethyl ester With sodium hydroxide In tetrahydrofuran at 20℃; for 24h;
Stage #2: With acetic acid In tetrahydrofuran; water
94%
With sodium hydroxide In ethanol Reflux;81%
3926-62-3

sodium monochloroacetic acid

139-02-6

sodium phenoxide

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
Stage #1: sodium monochloroacetic acid; sodium phenoxide In water at 90℃; for 2h;
Stage #2: With hydrogenchloride In water at 30℃; pH=0;
95%
122-99-6

2-Phenoxyethanol

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 5h; pH=9.8 - 10.1; Electrolysis;91%
With Jones reagent In acetone at 0℃; for 1h;75%
With potassium hydroxide In tert-butyl alcohol at 50℃; Electrochemical reaction;43%
With NADH oxidase; nicotinamide adenine dinucleotide; 2-phenylethanol dehydrogenase; phenylacetaldehyde dehydrogenase at 25℃; under 760.051 Torr; for 12h; pH=9.0;35 % Chromat.
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; sodium hydrogencarbonate; sodium carbonate In water; acetonitrile pH=10; Electrochemical reaction; chemoselective reaction;91 %Spectr.
7493-74-5

allyl 2-phenoxyacetate

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With formic acid; triethylamine In acetonitrile at 80℃; for 2.5h; Inert atmosphere;86%
With iodine; dimethyl sulfoxide for 0.5h; Heating;80%
With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere;70%
93-76-5

2,4,5-Trichlorophenoxyacetic acid

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With borane-ammonia complex In water; isopropyl alcohol at 50℃; for 5h; Sealed tube;87%
In methanol; water at 18 - 20℃; for 4h; electrochemical reactions; electrolyte: n-Bu4NBr, CF3COOH; cathode 5percent Pd/FE-600 carbon felt, anode Pt-foil; Yield given;
Stage #1: 2,4,5-Trichlorophenoxyacetic acid With 1,2-diphenyl-1,2-disodiumethane In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water chemoselective reaction;
Multi-step reaction with 2 steps
1: sodium hydroxide; hydrogen; / 25 °C / pH 11 / Inert atmosphere
2: sodium hydroxide; hydrogen; / 25 °C / pH 11 / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide; hydrogen; / 25 °C / pH 11 / Inert atmosphere
2: sodium hydroxide; hydrogen; / 25 °C / pH 11 / Inert atmosphere
3: sodium hydroxide; hydrogen; / 25 °C / pH 11 / Inert atmosphere
View Scheme
105-36-2

ethyl bromoacetate

108-95-2

phenol

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
Stage #1: ethyl bromoacetate; phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;
Stage #2: With potassium hydroxide In methanol; water at 80℃; for 4h;
65%
Stage #1: ethyl bromoacetate; phenol With potassium carbonate In dimethyl sulfoxide at 50℃; for 6h;
Stage #2: With water; sodium hydroxide In acetone at 50℃; for 3h;
Stage #3: With hydrogenchloride In water at 25℃; pH=1 - 2;
2065-23-8

methyl 2-phenoxyacetate

122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 25℃; for 72h;97%
With potassium hydroxide In methanol at 35℃; for 1h;96%
With potassium fluoride; thiophenol In various solvent(s) at 190℃; for 0.166667h;90%
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    Product Name: Phenoxyacetic acid CAS: 122-59-8 MF: C8H8O3 MW: 152.15 EINECS: 204-556-7 Mol File: 122-59-8.mol Phenoxyacetic acid Structure Phenoxyacetic acid Chemical Properties Melting point 98-100 °C (lit.) Boiling point

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Phenoxyacetic acid is an organic compound with the formula C8H8O3. The IUPAC name of this chemical is 2-phenoxyacetic acid. With the CAS registry number 122-59-8, it is also named as acetic acid, 2-phenoxy-. The product's classification code is Skin / Eye Irritant. Besides, it should be stored in a closed cool and dry place. It is mainly used for the manufacture of dyes, drugs, pesticides, fungicides and so on.

Physical properties about Phenoxyacetic acid are: (1)ACD/LogP: 1.34; (2)ACD/LogD (pH 5.5): -0.98; (3)ACD/LogD (pH 7.4): -2.29; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 35.53 Å2; (12)Index of Refraction: 1.54; (13)Molar Refractivity: 39.12 cm3; (14)Molar Volume: 124.5 cm3; (15)Polarizability: 15.51×10-24cm3; (16)Surface Tension: 46.6 dyne/cm; (17)Density: 1.221 g/cm3; (18)Flash Point: 115.1 °C; (19)Enthalpy of Vaporization: 55.35 kJ/mol; (20)Boiling Point: 285 °C at 760 mmHg; (21)Vapour Pressure: 0.00135 mmHg at 25°C.

Preparation: this chemical can be prepared by chloroacetic acid and phenol. This reaction will need reagent NaOH and solvent H2O by heating.



Uses of Phenoxyacetic acid: it can be used to produce phenoxymethyl phenoxyacatete. It will need reagent I2, HgO and solvent CCl4 with reaction time of 5 hours. The yield is about 100%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)COc1ccccc1
(2)InChI: InChI=1/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
(3)InChIKey: LCPDWSOZIOUXRV-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
(5)Std. InChIKey: LCPDWSOZIOUXRV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 unreported 1400mg/kg (1400mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(1), Pg. 25, 1981.
mouse LD50 intravenous 1gm/kg (1000mg/kg)   Pharmazie. Vol. 18, Pg. 642, 1963.
mouse LD50 oral 3750mg/kg (3750mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(1), Pg. 25, 1981.
rabbit LD50 oral > 200mg/kg (200mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 887, 1979.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 887, 1979.
rat LD50 intraperitoneal 323mg/kg (323mg/kg)   Travaux de la Societe de Pharmacie de Montpellier. Vol. 34, Pg. 121, 1974.
rat LD50 oral 1500mg/kg (1500mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 94, 1990.