4-Carboxyphenylacetic acid supplier

Name
4-CARBOXYPHENYLACETIC ACID
EINECS
CAS No. 501-89-3
Article Data35
CAS DataBase
Density 1.392 g/cm³
Solubility
Melting Point 234-236 °C(Solv: water (7732-18-5))
Formula C₉H₈O₄
Boiling Point 402.5 °C at 760 mmHg
Molecular Weight 180.16
Flash Point 211.4 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms p-Toluicacid, a-carboxy- (6CI,7CI,8CI);(p-Carboxyphenyl)acetic acid;4-(Carboxymethyl)benzoic acid;p-(Carboxymethyl)benzoic acid;p-Carboxyphenoxyacetic acid;Homoterephthalic acid;p-Carboxy-a-toluic acid;a-Carboxy-p-toluic acid;NSC 2109;
PSA 74.60000
LogP 1.01190

Synthetic route

: 512787-38-1
methyl 4-(2-oxo-2-(pyrrolidin-1-yl)ethyl)benzoate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 24h; Heating;	94%

: 50685-26-2
4-(cyanomethyl)benzoic acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sulfuric acid for 6h; Heating;	90%
With sodium hydroxide In hydrogenchloride	11.7%
With sodium hydroxide In hydrogenchloride	11.7%
With sulfuric acid at 80℃; for 10h;
With sodium hydroxide; water In dimethyl sulfoxide at 110℃; for 4.5h;

: 76469-88-0
methyl 4-(cyanomethyl)benzoate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sulfuric acid In water at 5℃;	87%
With sodium hydroxide In methanol at 90℃;	70%
With sodium hydroxide
With sulfuric acid; water at 125℃;
With water; sodium hydroxide In methanol at 90℃; for 12h;

: 201230-82-2
carbon monoxide

: 85267-37-4
(4-Cyano-benzyl)-triethyl-ammonium; bromide

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; dicobalt octacarbonyl at 65℃; Irradiation;	85%

: 5462-71-5
4-cyanophenylacetic acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With water; potassium hydroxide at 110℃; for 4h;	81%

: sodium 4-acetyl-phenylacetate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Stage #1: sodium 4-acetyl-phenylacetate With potassium hydroxide In 1,4-dioxane; water at 0℃; for 0.166667h; Cooling with ice; Stage #2: With bromine In 1,4-dioxane; water at 0℃; for 3h; Cooling with ice;	80.2%

: 1878-66-6
4-chlorophenylacetic Acid

: 201230-82-2
carbon monoxide

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
dicobalt octacarbonyl In sodium hydroxide at 65℃; for 15h;	80%

: 201230-82-2
carbon monoxide

: 85267-35-2
N-(4-bromobenzyl)-N,N,N-triethylammonium bromide

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; dicobalt octacarbonyl at 65℃; Irradiation;	80%

: 201230-82-2
carbon monoxide

: 17201-43-3
4-cyanobenzyl bromide

A: 501-89-3
4-(carboxymethyl)benzoic acid

B: 29903-10-4
4,4'-(2-oxopropane-1,3-diyl)dibenzonitrile

Conditions

Conditions	Yield
With sodium hydroxide; cobalt tricarbonyl nitrosyl; trimethyldodecylammonium chloride In benzene under 760 Torr; Ambient temperature;	A 80% B 2%

...Expand

: 201230-82-2
carbon monoxide

: 5197-90-0
(4-chlorobenzyl)-tri-(ethyl)-ammonium chloride

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; dicobalt octacarbonyl at 65℃; Irradiation;	75%

: 14062-24-9
4-chloro-benzeneacetic acid, ethyl ester

: 201230-82-2
carbon monoxide

: 71-36-3
butan-1-ol

A: 501-89-3
4-(carboxymethyl)benzoic acid

B: n-butyl (4-butoxycarbonylphenyl)acetate

C: (4-butoxycarbonylphenyl)acetic acid

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium carbonate; bis(benzonitrile)palladium(II) dichloride; 1-(dicyclohexylphosphino)-2-[1-(dicyclohexylphosphino)ethyl]ferrocene at 145℃; under 750.06 Torr; for 16h;	A n/a B 68% C n/a

...Expand

: 1528-42-3
ethyl 4-acetylphenylacetate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Stage #1: ethyl 4-acetylphenylacetate With lithium hydroxide monohydrate; sodium hydroxide In tetrahydrofuran at 20℃; Stage #2: With iodine; sodium hydroxide In water at 20 - 90℃; for 2.5h;	50%
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: iodine; aq. NaOH solution View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C 2.1: potassium hydroxide / water; 1,4-dioxane / 0.17 h / 0 °C / Cooling with ice 2.2: 3 h / 0 °C / Cooling with ice View Scheme

: 876-31-3
4-(cyanomethyl)benzonitrile

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide at 95℃; for 2h; Sealed tube;	46%
With sulfuric acid
With hydrogenchloride at 130℃;
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: hydrochloric acid View Scheme

: 26496-94-6
Ethyl 4-(bromomethyl)benzoate

: 201230-82-2
carbon monoxide

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;	43%

: 4395-87-3
(4-isopropylphenyl)acetonitrile

A: 100-21-0
terephthalic acid

B: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With nitric acid

: 7398-52-9
4-acetyl-phenylacetic acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; iodine

: 4476-28-2
(4-isopropylphenyl)acetic acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With nitric acid

: (4-carbamoyl-phenyl)-acetic acid amide

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 4-(3,5-Dimethyl-phenoxycarbonylmethyl)-benzoic acid

A: 501-89-3
4-(carboxymethyl)benzoic acid

B 3,5-Dimethylphenol: 3,5-Dimethylphenol

Conditions

Conditions	Yield
With phosphate buffer In acetonitrile at 21℃; Rate constant; other buffer; different pH; also in the presence of amidine or molecularly imprinted polymers as catalysts;

A

B tert-octylphenol: tert-octylphenol

Conditions

Conditions	Yield
With phosphate buffer In acetonitrile at 21℃; Rate constant; other buffer; different pH; also in the presence of amidine or molecularly imprinted polymers as catalysts;

: 7647-01-0
hydrogenchloride

: 876-31-3
4-(cyanomethyl)benzonitrile

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
at 130℃;

: 4476-28-2
(4-isopropylphenyl)acetic acid

: 7697-37-2
nitric acid

: 501-89-3
4-(carboxymethyl)benzoic acid

: 14062-24-9
4-chloro-benzeneacetic acid, ethyl ester

: 201230-82-2
carbon monoxide

: 71-36-3
butan-1-ol

A: 501-89-3
4-(carboxymethyl)benzoic acid

B: (4-butoxycarbonylphenyl)acetic acid

Conditions

Conditions	Yield
With molecular sieve; 1-(dicyclohexylphosphino)-2-[1-(dicyclohexylphosphino)ethyl]ferrocene; sodium carbonate; bis(benzonitrile)palladium(II) dichloride In butan-1-ol at 145℃; under 750.06 Torr; for 16h;

...Expand

: 1571-08-0
methyl 4-formylbenzoate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / PPh3 / CH2Cl2 / 0.5 h / 0 °C 2: 98 percent / H2O / ethyl acetate / 1 h / 20 °C 3: 94 percent / aq. HCl / dioxane / 24 h / Heating View Scheme

: 253684-21-8
1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / H2O / ethyl acetate / 1 h / 20 °C 2: 94 percent / aq. HCl / dioxane / 24 h / Heating View Scheme

: 99-75-2
4-methyl-benzoic acid methyl ester

Cp2Ti(Cl)CH2Al(CH3)2: Cp2Ti(Cl)CH2Al(CH3)2

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / Br2 / benzene / 2 h / Irradiation 2: 74 percent / ethanol; H2O / 3 h / Heating 3: 87 percent / sulfuric acid / H2O / 5 °C View Scheme

: 2417-72-3
Methyl 4-(bromomethyl)benzoate

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / ethanol; H2O / 3 h / Heating 2: 87 percent / sulfuric acid / H2O / 5 °C View Scheme
Multi-step reaction with 2 steps 1: NaCN 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 1: water; methanol / 5 h / Reflux 2: sodium hydroxide / methanol / 90 °C View Scheme
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / acetonitrile / 12 h / 25 °C 2: sodium hydroxide; water / methanol / 12 h / 90 °C View Scheme

: 1642-81-5
p-(chloromethyl)benzoic acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / aq. NaHCO3 / tetrahydrofuran / 48 h / 20 - 25 °C 2: 90 percent / aq. H2SO4 / 6 h / Heating View Scheme

: 6232-88-8
4-bromomethylbenzoic Acid

: 501-89-3
4-(carboxymethyl)benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / acetonitrile; H2O / 2 h / Heating 2: 50percent H2SO4 / 10 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: methanol. H2SO4 2: NaCN 3: aqueous NaOH View Scheme

: 67-56-1
methanol

: 501-89-3
4-(carboxymethyl)benzoic acid

: 52787-14-1
methyl 4-(2-methoxy-2-oxoethyl)benzoate

Conditions

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 50℃; for 4h;	95%
With sulfuric acid at 90℃; for 19h;	93%
With sulfuric acid a) from 20 deg C to 25 deg C, 3 d, b) reflux, 4.5 h;	91%

: 67-56-1
methanol

: 501-89-3
4-(carboxymethyl)benzoic acid

: 87524-66-1
4-(methoxycarbonylmethyl)benzoic acid

Conditions

Conditions	Yield
With thionyl chloride at 20℃;	91%
With amberlyst-15 at 20℃; for 12h; Esterification;	88%
With thionyl chloride at 20℃; for 5.5h;	88%

: 67-56-1
methanol

: 501-89-3
4-(carboxymethyl)benzoic acid

A: 52787-14-1
methyl 4-(2-methoxy-2-oxoethyl)benzoate

B: 87524-66-1
4-(methoxycarbonylmethyl)benzoic acid

Conditions

Conditions	Yield
With thionyl chloride at 25 - 27℃; for 7h; Esterification;	A 5% B 90%
With nickel dichloride for 10h; Heating;	A 6% B 85%
With phosphorus pentoxide; copper(II) sulfate; sodium sulfate for 4h; Heating;	A 20% B 70%

...Expand

: 501-89-3
4-(carboxymethyl)benzoic acid

: 1642-81-5
p-(chloromethyl)benzoic acid

Conditions

Conditions	Yield
With tert-butylhypochlorite; Ag(Phen)2OTf In acetonitrile at 20℃; for 25h; Inert atmosphere;	90%

: 553-26-4
4,4'-bipyridine

: copper(II) nitrate trihydrate

: 501-89-3
4-(carboxymethyl)benzoic acid

: Cu2(4-carboxymethylbenzoate)(4,4'-bipyridine)2*3H2O

Conditions

Conditions	Yield
With Et3N In water; acetonitrile High Pressure; 1 equiv. of metal-salt, 1 equiv. of the acid and 1 equiv. of the 4,4'-bpy together with a drop of Et3N in 1:9 MeCN:H2O were sealed into a teflon-lined stainless steel vessel, 160 °C for 3 d; slow cooling to room temp., elem. anal.;	89%

...Expand

: 501-89-3
4-(carboxymethyl)benzoic acid

: 63468-90-6
phenylglyoxylic acid potassium salt

: 104594-75-4
2-(4-Carboxyphenyl)-3-phenylmaleic anhydride

Conditions

Conditions	Yield
With acetic anhydride for 3h; Heating;	87%
With acetic anhydride In water	28 g (87 mole %)

: 4916-57-8
1,2-bis(4'-pyridyl)ethane

: 501-89-3
4-(carboxymethyl)benzoic acid

: 5743-04-4
cadmium(II) acetate dihydrate

: [Cd3(homoterephthalate)2(1,2-bis(4-pyridyl)ethane)2(acetate)2]n

Conditions

Conditions	Yield
In ethanol; water at 120℃; for 96h; Autoclave;	85%

...Expand

: 553-26-4
4,4'-bipyridine

: cobalt(II) nitrate hexahydrate

: 501-89-3
4-(carboxymethyl)benzoic acid

: Co(4-carboxymethylbenzoate)(4,4'-bipyridine)(H2O)3*H2O

Conditions

Conditions	Yield
With Et3N In water; acetonitrile High Pressure; 1 equiv. of metal-salt, 1 equiv. of the acid and 1 equiv. of the 4,4'-bpy together with a drop of Et3N in 1:9 MeCN:H2O were sealed into a teflon-lined stainless steel vessel, 120 °C for 3 d; slow cooling to room temp., elem. anal.;	84%

...Expand

: 60-12-8
2-phenylethanol

: 501-89-3
4-(carboxymethyl)benzoic acid

: 2-phenethyl 4-(2-oxo-2-phenethoxyethyl)benzoate

Conditions

Conditions	Yield
With C10H10Zr(2+)2CF3O3S(1-)C4H8O at 80℃; for 24h; Sealed tube;	77%

: 501-89-3
4-(carboxymethyl)benzoic acid

: 4-(carboxymethyl)-2-iodobenzoic acid

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; iodine; silver(I) acetate; triethylamine at 23℃; for 18h; Sealed tube; regioselective reaction;	77%

: 288-88-0
1,2,4-Triazole

: 501-89-3
4-(carboxymethyl)benzoic acid

: 7732-18-5
water

: 5743-04-4
cadmium(II) acetate dihydrate

: {[Cd3(homoterephthalate)(1,2,4-triazolate)3(acetate)(H2O)4]*4H2O}n

Conditions

Conditions	Yield
In ethanol at 120℃; for 96h; Autoclave;	76%

...Expand

: 501-89-3
4-(carboxymethyl)benzoic acid

: 105589-77-3
2-(2-trityloxyethoxy)ethanol

: 1206723-96-7
C55H52O8

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 30℃; for 14h;	71%

: 501-89-3
4-(carboxymethyl)benzoic acid

: 444667-11-2
2-(4-carboxy-2-nitrophenyl)-acetic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 3h;	70%
With nitric acid at 60 - 70℃;
With sulfuric acid; nitric acid at 0℃; for 4h;

: 553-26-4
4,4'-bipyridine

: 501-89-3
4-(carboxymethyl)benzoic acid

: 6156-78-1
manganese (II) acetate tetrahydrate

: Mn(4-carboxymethylbenzoate)2(4,4'-bipyridine)2(H2O)2

Conditions

Conditions	Yield
With Et3N In water; acetonitrile High Pressure; 1 equiv. of metal-salt, 1 equiv. of the acid and 1 equiv. of the 4,4'-bpy together with a drop of Et3N in 1:9 MeCN:H2O were sealed into a teflon-lined stainless steel vessel, 120 °C for 3 d; slow cooling to room temp., elem. anal.;	67%

...Expand

: 69506-86-1
1,1'-(1,4-butanediyl)bis(imidazole)

: zinc nitrate tetrahydrate

: 501-89-3
4-(carboxymethyl)benzoic acid

: 1207858-69-2
(4-carboxymethylbenzoate)(1,1'-(1,4-butanediyl)bis(imidazole))zinc(II) monohydrate

Conditions

Conditions	Yield
With Et3N In water; acetonitrile High Pressure; Zn salt, 4-carboxymethylbenzoic acid, 1,1'-(1,4-butanediyl)bis(imidazole), Et3N (1:1:1:1.2) in CH3CN and H2O heated in an autoclave at 120°C for 3 d; slowly cooled to room temp., washed (CH3OH), elem. anal.;	67%

...Expand

: 501-89-3
4-(carboxymethyl)benzoic acid

: 5743-04-4
cadmium(II) acetate dihydrate

: 1135-32-6
trans-1,2-bis(4-pyridyl)ethylene

: [Cd(homoterephthalate)(1,2-bis(4-pyridyl)ethylene)]n

Conditions

Conditions	Yield
In ethanol; water at 120℃; for 96h; Autoclave;	65%

...Expand

: 501-89-3
4-(carboxymethyl)benzoic acid

: 1111-72-4
carbon dioxide

: C8(13)CH8O4

Conditions

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 0.5h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;	65%

: 501-89-3
4-(carboxymethyl)benzoic acid

: 619-65-8
4-cyanobenzoic Acid

Conditions

Conditions	Yield
With iron(III) trifluoromethanesulfonate; sodium nitrite In dimethyl sulfoxide at 50℃; for 10h; Inert atmosphere; Sealed tube;	61%

4-Carboxyphenylacetic acid Specification

The Benzeneacetic acid, 4-carboxy-, with the CAS registry number 501-89-3, is also known as Carboxyphenylaceticacid. This chemical's molecular formula is C₉H₈O₄and molecular weight is 180.16. What's more, its IUPAC name is called 4-(carboxymethyl)benzoic acid.

Physical properties of Benzeneacetic acid, 4-carboxy-: (1)ACD/LogP: 1.18; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 52.6 Å²; (11)Index of Refraction: 1.6; (12)Molar Refractivity: 44.29 cm³; (13)Molar Volume: 129.4 cm³; (14)Surface Tension: 65.2 dyne/cm; (15)Density: 1.392 g/cm³; (15)Flash Point: 211.4 °C; (16)Enthalpy of Vaporization: 68.94 kJ/mol; (17)Boiling Point: 402.5 °C at 760 mmHg; (18)Vapour Pressure: 3.34E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by4-cyanomethyl-benzoic acid methyl ester. This reaction will need reagent sulfuric acid and solvent water. The yield is about 87%.

Uses of Benzeneacetic acid, 4-carboxy-: it can be used to produce (4-methoxycarbonyl-phenyl)-acetic acid methyl ester at temperature of 20 - 25 °C. This reaction will need reflux for 4.5 hours. It will need reagent sulphuric acid. The yield is about 91%.

You can still convert the following datas into molecular structure:
(1)SMILES: C1=CC(=CC=C1CC(=O)O)C(=O)O
(2)InChI: InChI=1S/C9H8O4/c10-8(11)5-6-1-3-7(4-2-6)9(12)13/h1-4H,5H2,(H,10,11)(H,12,13)
(3)InChIKey: DMEDOWYXHVUPMO-UHFFFAOYSA-N

Product Name

4-CARBOXYPHENYLACETIC ACID

Synthetic route

4-Carboxyphenylacetic acid Specification

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