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4-Hydroxyphenylacetic acid
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Name

4-Hydroxyphenylacetic acid

 EINECS 205-851-3
CAS No. 156-38-7 Density 1.319 g/cm3
PSA 57.53000 LogP 1.01930
Solubility Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water. Melting Point 148-151 °C(lit.)
Formula C8H8O3 Boiling Point 346.6 °C at 760 mmHg
Molecular Weight 152.15 Flash Point 177.6 °C
Transport Information N/A Appearance white or light yellow crystalline powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 156-38-7 (4-Hydroxyphenylacetic acid) Hazard Symbols IrritantXi
Synonyms

Acetic acid, (p-hydroxyphenyl)-;4-HPA;2-(4-hydroxyphenyl)acetate;Para Hydroxy Phenyl Acetic;P-Hydroxyphenyl acetic acid;4-Hydroxy Phenyl Acetic Acid;4-Hydroxyphenylaceticacid;4-Hydroxyphenyl acetic acid;4-Carboxymethylphenol;benzeneacetic acid, 4-hydroxy-;4-10-00-00543 (Beilstein Handbook Reference);(p-Hydroxyphenyl)acetic acid;

Article Data 132

4-Hydroxyphenylacetic acid Synthetic route

4-Methoxyphenylacetic acid

4-Methoxyphenylacetic acid

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - -15℃; for 4h; Inert atmosphere;99%
With boron tribromide In dichloromethane at -78℃; for 0.5h;93%
With hydrogen bromide; cetyltributylphosphonium bromide for 7.5h; Heating;87%
58609-13-5

4-(benzyloxy)phenylacetic acid benzyl ester

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 3h;99%

2-(diethylamino)-1-(4-hydroxyphenyl)ethanone hydrochloride

A

156-38-7

4-hydroxyphenylacetate

B

660-68-4

diethyl amine hydrochloride

Conditions
ConditionsYield
In aq. buffer pH=4 - 7.4; pH-value; Irradiation;A 99%
B 99%

1-(4-hydroxyphenyl)-2-(piperidin-1-yl)ethanone hydrobromide

A

156-38-7

4-hydroxyphenylacetate

B

14066-85-4

piperidine hydrobromide

Conditions
ConditionsYield
In aq. acetate buffer pH=5.6; pH-value; Irradiation;A 99%
B 99%
19745-72-3

ω-amino-4-hydroxyacetophenone hydrochloride

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
In aq. acetate buffer pH=5.6; pH-value; Irradiation;99%
7400-08-0

p-Coumaric Acid

A

156-38-7

4-hydroxyphenylacetate

B

501-94-0

p-hydroxyphenethyl alcohol

Conditions
ConditionsYield
With β-D-glucose; oxygen for 18h; Reagent/catalyst; Enzymatic reaction;A n/a
B 97.3%
aqueous sulphuric acid

aqueous sulphuric acid

4-hydroxymandelic acid sodium salt monohydrate

aqueous chromic chloride

aqueous chromic chloride

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
With zinc In water; paraffin oil97%
52449-43-1

(4-chloro-phenyl)-acetic acid methyl ester

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
With sodium hydroxide96%

BrH*C9H11NO2

A

156-38-7

4-hydroxyphenylacetate

B

6876-37-5

methylammonium bromide

Conditions
ConditionsYield
In water pH=5.6; pH-value; Irradiation;A 95%
B 95%

2-fluoro-1-(4-hydroxyphenyl)ethanone

156-38-7

4-hydroxyphenylacetate

Conditions
ConditionsYield
In acetonitrile Quantum yield; Solvent; UV-irradiation;95%

4-Hydroxyphenylacetic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Hydroxyphenylacetic acid Specification

4-Hydroxyphenylacetic acid, with the CAS NO.156-38-7, is an important intermediate which is used for syntheses of substances useful for pharmaceuticals. Therefore, it is generally beneficial that the acid is advantageously manufactured on an industrial scale. It is also called (p-hydroxyphenyl)-aceticaci; 4-carboxymethylphenol; 4-hydroxy-benzeneaceticaci; 4-hydroxybenzeneaceticacid; 4-hydroxyphenylethanoicacid; Acetic acid, (p-hydroxyphenyl)-; ethanoicacid,4-hydroxyphenyl-.

Physical properties about 4-Hydroxyphenylacetic acid are: (1)ACD/LogP: 0.692; (2)ACD/LogD (pH 5.5): -0.39; (3)ACD/LogD (pH 7.4): -2.19; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5):4.70; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.596; (12)Molar Refractivity: 39.248 cm3; (13)Molar Volume: 115.306 cm3; (14)Polarizability: 15.559 10-24cm3; (15)Surface Tension: 59.8230018615723 dyne/cm; (16)Density: 1.32 g/cm3; (17)Flash Point: 177.631 °C; (18)Enthalpy of Vaporization: 62.351 kJ/mol; (19)Boiling Point: 346.627 °C at 760 mmHg

Preparation of 4-Hydroxyphenylacetic acid: A method in which anisole, which is a starting material, is subjected to chloromethylation and a cyanation to be thereby converted to 4-methoxyphenylacetonitrile (Organikum, Berlin, nine edit., p. 363); and the resultant4-methoxyphenylacetonitrile is saponified to produce an acid, which is subsequently treated with hydriodic acid to eliminate an ether, whereby 4-hydroxyphenylacetic acid is obtained as the desired product.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Avoid contact with skin and eyes;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11);
(2)InChIKey=XQXPVVBIMDBYFF-UHFFFAOYSA-N;
(3)Smilesc1(ccc(O)cc1)CC(O)=O;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3500mg/kg (3500mg/kg)   Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958.

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