4-Hydroxyphenylacetic acid supplier

Name
4-Hydroxyphenylacetic acid
EINECS 205-851-3
CAS No. 156-38-7
Article Data132
CAS DataBase
Density 1.319 g/cm³
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
Appearance white or light yellow crystalline powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 57.53000
LogP 1.01930

Synthetic route

4-Methoxyphenylacetic acid: 4-Methoxyphenylacetic acid

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With zinc In water; paraffin oil	97%

...Expand

: 52449-43-1
(4-chloro-phenyl)-acetic acid methyl ester

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium hydroxide	96%

: BrH*C9H11NO2

A: 156-38-7
4-hydroxyphenylacetate

B: 6876-37-5
methylammonium bromide

Conditions

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

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

: 156-38-7
4-hydroxyphenylacetate

Conditions

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

: 14191-95-8
4-cyanomethylphenol

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.5h; microwave irradiation;	92%
With hydrogenchloride
With potassium hydroxide
With sodium hydroxide In water; toluene

: 182296-61-3
2-bromomethyl-2-(4'-hydroxyphenyl)-1,3-dioxolane

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium hydroxide In water at 95℃; for 0.666667h;	90%

: 2-chloromethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium hydroxide In water at 95℃; for 1h;	88%

: 2-bromomethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium hydroxide In water at 90 - 95℃; for 0.666667h;	88%

: 17194-82-0
2-(4-hydroxyphenyl)acetamide

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 1h; Hydrolysis;	86%

: C15H15NO5S

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium tetrahydroborate; trifluoroacetic acid In dichloromethane at 15 - 25℃;	85.5%

: 4-hydroxymandelic acid sodium salt monohydrate

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With concentrated aqueous hydrochloric acid; palladium In water	85%

: 1798-06-7
(4-iodophenyl)acetic acid

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 100℃; for 6h;	84%
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h;	84%

: 501-94-0
p-hydroxyphenethyl alcohol

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium hydroxide; oxygen; lead acetate; palladium on activated charcoal In water at 90℃; under 3800 Torr; for 3h;	80.5%
With lithium aluminium tetrahydride

: 156-39-8
4-Hydroxyphenylpyruvic acid

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sodium perborate In water for 48h; Ambient temperature;	80%
Multi-step reaction with 2 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme
With oxygen; ascorbic acid

: 6305-04-0
p-hydroxyphenacyl chloride

A: 156-38-7
4-hydroxyphenylacetate

B: 108791-64-6
1,4-bis(4-hydroxyphenyl)butan-1,4-dione

C: 99-93-4
4-Hydroxyacetophenone

Conditions

Conditions	Yield
With methyloxirane In water; acetonitrile for 4h; Irradiation;	A 75% B 10% C 5%

...Expand

: Sodium; (S)-hydroxy-(4-hydroxy-phenyl)-acetate

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With formic acid; phosphoric acid; sodium hydrogensulfite In water at 100℃; under 3750.3 Torr; for 9h; 1.1 mol HCOOH;	73%

: 2-bromomethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane

A: 156-38-7
4-hydroxyphenylacetate

B: 2,2-dimethyl-3-hydroxypropyl (4-hydroxyphenyl acetate)

Conditions

Conditions	Yield
With potassium acetate In water at 95 - 100℃; for 1h;	A 11.7% B 69.3%

: 1198-84-1
4-hydroxymandelic acid

: 156-38-7
4-hydroxyphenylacetate

Conditions

Conditions	Yield
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 40℃; for 48h; Inert atmosphere;	62.2%

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

A: 156-38-7
4-hydroxyphenylacetate

B: 4-hydroxyphenylacetic acid methyl-d3 ester

Conditions

Conditions	Yield
In d(4)-methanol; water-d2 Quantum yield; UV-irradiation;	A 39% B 59%

: N-[2-(4-hydroxyphenyl)-2-oxoethyl]phenylalanine hydrochloride methyl ester

A: 156-38-7
4-hydroxyphenylacetate

B: 99-93-4
4-Hydroxyacetophenone

Conditions

Conditions	Yield
In aq. phosphate buffer pH=5.6; pH-value; Irradiation;	A 46% B 55%

: triethyl-[2-(4-hydroxyphenyl)-2-oxoethyl]ammonium bromide

A: 156-38-7
4-hydroxyphenylacetate

B: 75-07-0
acetaldehyde

C: 109-89-7
diethylamine

D: 121-44-8
triethylamine

E: 99-93-4
4-Hydroxyacetophenone

Conditions

Conditions	Yield
In aq. acetate buffer pH=4; pH-value; Irradiation;	A 20% B 24% C 45% D 51% E 18%

...Expand

: 19745-72-3
ω-amino-4-hydroxyacetophenone hydrochloride

A: 156-38-7
4-hydroxyphenylacetate

B: 108791-64-6
1,4-bis(4-hydroxyphenyl)butan-1,4-dione

C: 99-93-4
4-Hydroxyacetophenone

Conditions

Conditions	Yield
In aq. phosphate buffer pH=7.4; pH-value; Irradiation;	A 49% B 8% C 33%

...Expand

: 67-56-1
methanol

: 156-38-7
4-hydroxyphenylacetate

: 14199-15-6
Methyl 4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sulfuric acid Heating;	100%
With sulfuric acid for 8h; Heating;	100%
With sulfuric acid	100%

: 156-38-7
4-hydroxyphenylacetate

: 64-17-5
ethanol

: 17138-28-2
(4-hydroxy-phenyl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid for 1h; Heating / reflux;	100%
With sulfuric acid for 2h; Reflux;	98%
With sulfuric acid In water for 8h; Reflux;	98%

: 156-38-7
4-hydroxyphenylacetate

: 37859-23-7
2-(p-hydroxyphenyl)acetyl chloride

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane	100%
With thionyl chloride Heating;
With oxalyl dichloride In chloroform Ambient temperature;

: 156-38-7
4-hydroxyphenylacetate

: 100-39-0
benzyl bromide

: 6547-53-1
2-[4-(benzyloxy)benzyl]acetic acid

Conditions

Conditions	Yield
With sodium iodide; potassium hydroxide In ethanol for 20h; Reflux;	100%
With potassium carbonate; tetrabutylammomium bromide In tetrahydrofuran at 30℃; for 0.5h;	93%
With potassium hydroxide In ethanol; water Heating;	67.8%

: 67-56-1
methanol

: 156-38-7
4-hydroxyphenylacetate

: 212688-02-3
3,5-dibromo-4-hydroxyphenylacetic acid methyl ester

Conditions

Conditions	Yield
With bromine	100%

: 156-38-7
4-hydroxyphenylacetate

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 2-(4-hydroxyphenyl)-N-methoxy-N-methylacetamide

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;	100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;

: 156-38-7
4-hydroxyphenylacetate

: 102-32-9
3,4-dihydroxyphenylacetate

Conditions

Conditions	Yield
With ascorbic acid In aq. phosphate buffer at 25℃;	99.7%
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7;	98%
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Glovebox;	91%

: 156-38-7
4-hydroxyphenylacetate

: 608-25-3
2-methylbenzene-1,3-diol

: 139256-03-4
2,4,4'-trihydroxy-3-methyldeoxybenzoin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 110℃; for 0.5h; Heating / reflux;	99%
With boron trifluoride diethyl etherate at 60 - 70℃; for 5h;	97%
With boron trifluoride diethyl etherate at 110℃; for 2h; Inert atmosphere;

: 156-38-7
4-hydroxyphenylacetate

: 108-69-0
3,5-dimethylaminoaniline

: 131179-77-6
N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	99%
With boric acid In toluene for 18h; Heating;	95%
With pyridine; FI-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 60℃; for 0.75h; Sealed tube;	86%

: 295320-01-3
(3,4-dichlorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine

: 156-38-7
4-hydroxyphenylacetate

: 295320-03-5
N-(3,4-dichlorophenyl)-2-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl}acetamide

Conditions

Conditions	Yield
With anhydrous phosphorus trichloride In chlorobenzene	99%

: 6602-54-6
2-chloro-3-pyridinecarbonitrile

: 156-38-7
4-hydroxyphenylacetate

: 2-(4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-chloro-3-pyridinecarbonitrile; 4-hydroxyphenylacetate With potassium carbonate In dimethyl sulfoxide at 60℃; for 14h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide	99%

: 156-38-7
4-hydroxyphenylacetate

: 108-46-3
recorcinol

: 17720-60-4
2,4,4'-trihydroxy deoxybenzoin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;	98%
With boron trifluoride diethyl etherate for 0.25h; Acylation; Friedel-Crafts reaction; Heating;	90%
With boron trifluoride diethyl etherate for 0.166667h; Heating;	88%

: 156-38-7
4-hydroxyphenylacetate

: 501-94-0
p-hydroxyphenethyl alcohol

Conditions

Conditions	Yield
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;	98%
With sodium tetrahydroborate; iodine In tetrahydrofuran for 2h; Heating;	88%
With lithium aluminium tetrahydride In tetrahydrofuran at 67℃; for 2.5h;	88%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 156-38-7
4-hydroxyphenylacetate

: 73158-83-5
4-hydroxyphenylacetic acid N-hydroxysuccinimide ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate	98%
With benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane; N,N-dimethyl-formamide	78%
With dicyclohexyl-carbodiimide In 1,4-dioxane	41%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Ambient temperature;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;

: 156-38-7
4-hydroxyphenylacetate

: 50541-93-0
4-amino-1-benzylpiperidine

: N-(1-benzylpiperidin-4-yl)-2-(4-hydroxyphenyl)-acetamide

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane for 2h; Ambient temperature;	98%
Stage #1: 4-hydroxyphenylacetate With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 3h; Stage #2: 4-amino-1-benzylpiperidine In tetrahydrofuran at 20℃; for 24h;	40%

: 156-38-7
4-hydroxyphenylacetate

: 106-95-6
allyl bromide

: 851318-54-2
allyl (p-allyloxyphenyl)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;	86%
Stage #1: 4-hydroxyphenylacetate With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2h; Stage #2: allyl bromide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 4.5h;	65%

: 3610-42-2
5-bromotryptamine

: 156-38-7
4-hydroxyphenylacetate

: 1201916-18-8
C18H17BrN2O2

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	98%

: 156-38-7
4-hydroxyphenylacetate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 114774-40-2
2-(4-((tert-butyldimethylsilyl)oxy)phenyl)acetic acid

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 16h;	98%
With 1H-imidazole In tetrahydrofuran at 0 - 25℃; for 2h;	82%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 2h;	66%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 1h;	60.7%
Stage #1: 4-hydroxyphenylacetate; tert-butyldimethylsilyl chloride With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With sodium carbonate In tetrahydrofuran at 20℃; for 1h;	60.7%

: 156-38-7
4-hydroxyphenylacetate

: 19039-15-7
(4-hydroxy-3-iodophenyl)acetic acid

Conditions

Conditions	Yield
With Iodine monochloride; acetic acid In dichloromethane at 20℃; for 50h;	98%

: 156-38-7
4-hydroxyphenylacetate

: 24744-58-9
(3,5-dibromo-4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With bromine In acetic acid at 15℃; for 96h;	97%
With bromine; acetic acid
With bromine; acetic acid
With bromine In acetic acid

: 156-38-7
4-hydroxyphenylacetate

: 67-63-0
isopropyl alcohol

: 41997-33-5
iso-propyl 4-hydroxyphenylacetate

Conditions

Conditions	Yield
With sulfuric acid Heating;	97%
With tetrachlorosilane for 7h; Heating;	92%
With Fe(3+)-K-10 montmorillonite clay for 8h; Heating;	90%
With sodium hydrogen sulfate; silica gel at 20℃; for 5.5h; Esterification;	89%
With hydrogenchloride Heating;

: 156-38-7
4-hydroxyphenylacetate

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 10214-84-3
N-(2-(3,4-dimethoxyphenyl)ethyl)-2-(4-hydroxyphenyl)acetamide

Conditions

Conditions	Yield
at 215℃; for 5h;	97%
In neat (no solvent) at 200℃; for 2h; Sealed tube; Inert atmosphere;	91%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	80.5%

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.

Product Name

4-Hydroxyphenylacetic acid

Synthetic route

4-Hydroxyphenylacetic acid Consensus Reports

4-Hydroxyphenylacetic acid Specification

Related Products

Hot Products