1878-66-6

Basic information

• Product Name: 4-Chlorophenylacetic acid
• Synonyms: 13) PARA CHLORO PHENYL ACETIC ACID;2-(4-chlorophenyl)acetic acid;4-CHLOROPHENYLACETIC ACID pure;4-Chlorophenylacetic;P-Chlorophenylacetic acid (4-Chlorophenylacetic acid);4-Chlorophenylacetic acid, 98% 100GR;4-Chlorophenylacetic acid, 98% 5GR;NSC 14285
• CAS NO: 1878-66-6
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 217-521-6
• Product Categories: Phenylacetic acid;Organic acids;C8;Carbonyl Compounds;Carboxylic Acids;Phenylacetic acid series;FINE Chemical & INTERMEDIATES;Aromatic Phenylacetic Acids and Derivatives
• Mol File: 1878-66-6.mol
• Article Data: 72

Chemical Properties

• Melting Point: 102-105 °C(lit.)
• Boiling Point: 241.44°C (rough estimate)
• Flash Point: 131.7 °C
• Appearance: White to cream/Powder
• Density: 1.2315 (rough estimate)
• Vapor Pressure: 0.000751mmHg at 25°C
• Refractive Index: 1.5660 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: soluble100mg/mL, clear, faintly yellow
• PKA: 4.19(at 25℃)
• BRN: 1072816
• CAS DataBase Reference: 4-Chlorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorophenylacetic acid(1878-66-6)
• EPA Substance Registry System: 4-Chlorophenylacetic acid(1878-66-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21-36/37/38
• Safety Statements: 36/37-24/25-36-26
• WGK Germany: 3
• RTECS: AG0590000
• F: 13
• TSCA: Yes
• Hazardous Substances Data: 1878-66-6(Hazardous Substances Data)

Usage

Chemical Properties

white to cream colored powder

Uses

Different sources of media describe the Uses of 1878-66-6 differently. You can refer to the following data:
1. 4-Chlorophenylacetic Acid is a chlorinated phenyl acetic acid that is an antitumor differentiation inducer and may be an effective therapeutic agent in neuroblastoma therapy. 4-Chlorophenylacetic Acid shows plant growth-regulating activity.
2. 4-Chlorophenylacetic Acid is a chlorinated phenyl acetic acid that is an antitumor differentiation inducer and may be an effective therapeutic agent in neuroblastoma therapy. 4-Chlorophenylacetic Acid shows plant growth-regulating activity.
3. 4-Chlorophenylacetic acid was used to study the mechanism of aerobic degradation of 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane by Ralstonia eutropha A5.

Definition

ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-chlorophenyl group.

General Description

4-Chlorophenylacetic acid possess anticancer properties. It is a novel therapeutic agent which can be useful in prevention or treatment of estrogen-sensitive breast cancer. It acts as carbon and energy supplement and is degraded by Pseudomonas sp. strain CBS3.

Purification Methods

Purify it as for 3-chlorophenylacetic acid. [Beilstein 9 III 2263, 9 IV 1674.]

InChI:InChI=1/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Synthetic route

p-chlorobenzyl cyanide (140-53-4) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With water; sodium hydroxide at 110 - 116℃; under 15001.5 Torr; for 0.05h; Concentration; Pressure; Temperature; Flow reactor;	99%
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.1h; Green chemistry;	96%
With potassium hydroxide In toluene at 160℃; for 0.5h; microwave irradiation;	92%

4-chloro-benzeneacetic acid, ethyl ester (14062-24-9) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	98%

carbon monoxide (201230-82-2) + 4-chlorobenzyl bromide (622-95-7) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 60℃; under 760 Torr; for 18h; Carbonylation;	95%
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Temperature; Reagent/catalyst; Autoclave;	95.2%
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;	79%
With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran at 55℃; for 3h;	78%

N-[(E)-2-(4-Chloro-phenyl)-1-cyano-vinyl]-4,N-dimethyl-benzamide (89244-19-9, 89244-20-2) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 6h; Heating;	95%

C14H21ClNO3P → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogen bromide at 100℃; for 0.166667h;	95%
With water; hydrogen bromide at 100℃; for 0.166667h; Inert atmosphere;	95%

4-Methoxybenzyl 2-(4-chlorophenyl)acetate (1575722-27-8) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With proton-exchanged montmorillonite In dichloromethane at 20℃;	95%

2-(4-chlorophenyl)-1-(pyrrolidin-1-yl)-ethanone (19202-19-8) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 30h; Heating;	94%

1-Chloro-4-(chloromethyl)benzene (104-83-6) + butan-1-ol (71-36-3) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
Stage #1: butan-1-ol With cobalt(II) sulfate at 80℃; under 3750.38 Torr; for 4h; Autoclave; Stage #2: 1-Chloro-4-(chloromethyl)benzene With sodium hydroxide In water at 80℃; under 3750.38 Torr; for 24h; Concentration; Pressure; Temperature; Autoclave;	93.6%

carbon monoxide (201230-82-2) + 1-chloro-4-(dibromomethyl)benzene (62037-06-3) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With potassium hydroxide; dicobalt octacarbonyl; N-benzyl-N,N,N-triethylammonium chloride In benzene under 760 Torr; for 8h; Ambient temperature;	92%

(4-chloro-phenyl)-acetic acid methyl ester (52449-43-1) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	92%
With potassium hydroxide In methanol for 4h; Ambient temperature;	50%
With water for 36h;	50%

4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)phenylglycinonitrile → 4-chlorophenylacetic Acid (1878-66-6) + N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)amine (888963-33-5)

Conditions	Yield
With hydrogen bromide; acetic acid In dichloromethane; water at 20℃; for 1h;	A 92% B n/a

carbon monoxide (201230-82-2) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Temperature; Reagent/catalyst; Solvent; Autoclave;	90%
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry; Stage #2: 1-Chloro-4-(chloromethyl)benzene With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction;	86%
With bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; under 11251.1 Torr; for 20h; Autoclave; regioselective reaction;	86%
With sodium hydroxide; cerium(III) chloride; cetyltrimethylammonim bromide; nickel cyanide In toluene at 85 - 95℃; under 1 Torr; for 6.5h;	82%
With water; palladium diacetate at 110℃; under 37503.8 Torr; for 4h; Ionic liquid;	84 %Chromat.

2-(4-chlorophenyl)-1-(morpholin-4-yl)-ethanethione (42945-85-7) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide for 0.0166667h; microwave irradiation;	90%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 100℃; for 8h;

1-Chloro-4-(chloromethyl)benzene (104-83-6) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide; cobalt tetracarbonyl anion In methanol at 55℃; for 4h;	84%
Multi-step reaction with 2 steps 1: dimethylsulfoxide / 5 h / 45 - 50 °C 2: KOH / aq. ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: alcohol / 120 - 130 °C / im Druckrohr 2: concentrated KOH-solution View Scheme
Multi-step reaction with 2 steps 1: alcohol; water 2: concentrated KOH-solution View Scheme
Multi-step reaction with 2 steps 1: ethanol; H2O / Heating 2: aq. KOH / ethanol / Heating View Scheme

carbon dioxide (124-38-9) + (4-chlorobenzylidene)hydrazine (52372-80-2) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	82%

4-vinylbenzyl chloride (1073-67-2) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With Oxone; iodine In 1,2-dimethoxyethane; water at 20℃; for 3h; regioselective reaction;	77%
With D-glucose; oxygen In aq. phosphate buffer at 30℃; for 10h; pH=8; Green chemistry; Enzymatic reaction; regioselective reaction;	75%

carbon monoxide (201230-82-2) + 1-chloro-4-(dibromomethyl)benzene (62037-06-3) → 4-chlorophenylacetic Acid (1878-66-6) + 4,4'-dichlorostylbene (5121-74-4)

Conditions	Yield
With potassium hydroxide; dicobalt octacarbonyl; 18-crown-6 ether; N-benzyl-N,N,N-triethylammonium chloride In benzene under 760 Torr; for 8h; Product distribution; Ambient temperature; other reagent systems, other temp., various benzal bromides;	A 70% B 12%
With potassium hydroxide; dicobalt octacarbonyl; 18-crown-6 ether In benzene under 760 Torr; for 8h; Ambient temperature;	A 32% B 39%

1-chloro-4-(2,2-dibromovinyl)benzene (77295-59-1) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
Stage #1: 1-chloro-4-(2,2-dibromovinyl)benzene With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h;	67%
With PEG-400; potassium hydroxide; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In dichloromethane at 60 - 65℃; for 17h;	56%
Multi-step reaction with 2 steps 1: 91 percent / H2O / ethyl acetate / 8 h / 20 °C 2: 94 percent / aq. HCl / dioxane / 30 h / Heating View Scheme

p-chlorobenzyl cyanide (140-53-4) → 4-chlorophenylacetic Acid (1878-66-6) + 2-(4-chlorophenyl)acetamide (20101-92-2)

Conditions	Yield
With potassium hydroxide In toluene at 160℃; for 0.166667h; microwave irradiation;	A 65% B 32%
With immobilized activated nitrilase In water Rate constant; Ambient temperature; effect of β-cyclodextrin;

2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (517920-59-1) + carbon dioxide (124-38-9) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h;	65%

1-Chloro-4-iodobenzene (637-87-6) + acetic acid (64-19-7) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With silver(I) acetate; sodium acetate; palladium dichloride at 130℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;	63%

lead(II) thiocyanate (592-87-0) + ((2-(4-chlorophenyl)-1-methoxyvinyl)oxy)trimethylsilane → 4-chlorophenylacetic Acid (1878-66-6) + methyl 2-(4-chlorophenyl)-2-thiocyanatoethanoate

Conditions	Yield
Stage #1: lead(II) thiocyanate With (Dichloroiodo)benzene In dichloromethane at 0℃; for 0.333333h; Stage #2: ((2-(4-chlorophenyl)-1-methoxyvinyl)oxy)trimethylsilane In dichloromethane at 0 - 20℃; Further stages.;	A 10% B 57%

hypofluorous acid trifluoromethyl ester (373-91-1) + 4-(4-chlorobenzylidene)-2,2,6,6-tetramethyl-3,5-dioxa-2,6-disilaheptane (75581-01-0) → 4-chlorophenylacetic Acid (1878-66-6) + 4-chloro-α-fluorobenzeneacetic acid (74590-69-5)

Conditions	Yield
In CFCl3; hexane; water	A 53% B n/a

formic acid (64-18-6) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 24h; Inert atmosphere;	53%

cis-2,3-epoxy-3-(4-chlorophenyl)propanenitrile (33984-97-3, 33984-98-4) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With boron trifluoride diethyl etherate; water In 1,4-dioxane at 175℃; for 0.5h; Microwave irradiation; Green chemistry;	52%

2-(4-Chlorophenyl)ethanol (1875-88-3) → 4-chlorophenylacetic Acid (1878-66-6) + 2-phenylethanol (60-12-8) + benzoic acid (65-85-0) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
With sodium hydroxide; oxygen; lead acetate; palladium on activated charcoal In water at 90℃; under 3800 Torr; for 3h;	A 36.5% B 36.8% C 3% D 4.7%

p-chlorophenacyl chloride (937-20-2) → 4-chlorophenylacetic Acid (1878-66-6) + 1,4-bis(4-chlorophenyl)butane-1,4-dione (24314-35-0) + para-chloroacetophenone (99-91-2)

Conditions	Yield
With methyloxirane In water; acetonitrile for 4h; Irradiation;	A 35% B 18% C 6%
With methyloxirane In water; acetone for 4h; Irradiation;	A 14% B 31% C 10%

carbon dioxide (124-38-9) + para-chlorotoluene (106-43-4) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With bis(2-pyridyl)methane; xanth-9-one; nickel(II) chloride hexahydrate; potassium tert-butylate In benzene at 20℃; under 760.051 Torr; for 4h; Irradiation; Schlenk technique;	33%

5-p-chlorophenyl-2-phenyl-4-tosyl-2-oxazoline (80225-01-0) → 4-chlorophenylacetic Acid (1878-66-6) + 5-(4-chlorophenyl)-2-phenyl-1,3-oxazole (80224-89-1) + p-toluene sulfinic acid (536-57-2) + benzamide (55-21-0)

Conditions	Yield
With potassium carbonate In methanol for 1.5h; Heating; Yields of byproduct given;	A n/a B 14% C n/a D n/a

3-(5-aminomethyl-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione hydrochloride + 2-picolinoyl chloride hydrochloride (39901-94-5) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.25h;	10%

4-chlorophenylacetic Acid (1878-66-6) + methanol (67-56-1) → (4-chloro-phenyl)-acetic acid methyl ester (52449-43-1)

Conditions	Yield
With hydrogenchloride for 1h; Heating;	100%
With monoammonium 12-tungstophosphate for 12h; Heating;	98%
With sulfuric acid at 0 - 5℃; for 4.16667h; Reflux;	98%

4-chlorophenylacetic Acid (1878-66-6) + ethanol (64-17-5) → 4-chloro-benzeneacetic acid, ethyl ester (14062-24-9)

Conditions	Yield
With sulfuric acid In benzene for 6h; Reflux;	100%
sulfuric acid at 20℃;	99%
With monoammonium 12-tungstophosphate for 12h; Heating;	98%

4-chlorophenylacetic Acid (1878-66-6) → 4-chlorophenacetyl chloride (25026-34-0)

Conditions	Yield
With thionyl chloride In dichloromethane	100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 23℃;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 18h;	90%

4-chlorophenylacetic Acid (1878-66-6) + benzaldehyde (100-52-7) → (2E)-2-(4-chlorophenyl)-3-phenylprop-2-enoic acid (10465-70-0, 73720-02-2, 20432-20-6)

Conditions	Yield
With acetic anhydride; triethylamine	100%
In acetic anhydride

4-chlorophenylacetic Acid (1878-66-6) + 2,4-diaminophenol dihydrochloride (137-09-7) → 2-(4-chlorobenzyl)-5-aminobenzoxazole (381200-35-7)

Conditions	Yield
With PPA at 195 - 198℃; for 1.5h;	100%
With polyphosphoric acid at 200℃; for 1.5h;	75%
With PPA Heating;

4-chlorophenylacetic Acid (1878-66-6) + 2,4-diaminophenol (95-86-3) → 2-(4-chlorobenzyl)-5-aminobenzoxazole (381200-35-7)

Conditions	Yield
With PPA at 195 - 198℃; for 1.5h;	100%

4-chlorophenylacetic Acid (1878-66-6) + methyl iodide (74-88-4) → (4-chloro-phenyl)-acetic acid methyl ester (52449-43-1)

Conditions	Yield
With potassium carbonate In acetone at 60℃;	100%
With potassium carbonate In acetone at 60℃;	100%
Stage #1: 4-chlorophenylacetic Acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 1h; Stage #2: methyl iodide In toluene at 20℃; for 48h;	50%

4-chlorophenylacetic Acid (1878-66-6) + N-cyclohexyl-cyclohexanamine (101-83-7) → C8H7ClO2*C12H23N

Conditions	Yield
In methanol at 20℃;	100%

4-chlorophenylacetic Acid (1878-66-6) + ethyl iodide (75-03-6) → 4-chloro-benzeneacetic acid, ethyl ester (14062-24-9)

Conditions	Yield
With 1,5-diazabicyclo[5.4.0]-undec-7-ene In N,N-dimethyl-formamide at 0℃;	99%

4-chlorophenylacetic Acid (1878-66-6) + 4-chlorophenylethylamine (156-41-2) → 2-(4-chlorophenyl)-N-[2-(4-chlorophenyl)ethyl]acetamide (325164-96-3)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	89%

4-chlorophenylacetic Acid (1878-66-6) + diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate (94746-87-9) → diethyl 3-(p-chlorophenyl)-4-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6,7-dicarboxylate (111877-27-1)

Conditions	Yield
With triethylamine In dichloromethane; acetic anhydride	99%

4-chlorophenylacetic Acid (1878-66-6) + DIMCARB (4137-10-4) → 2-(4-chlorophenyl)-N,N-dimethylacetamide (33297-39-1)

Conditions	Yield
With zirconium(IV) chloride In toluene at 120℃; for 24h; Inert atmosphere; Molecular sieve;	99%

4-chlorophenylacetic Acid (1878-66-6) + phenethylamine (64-04-0) → 2-(4-chlorophenyl)-N-(2-phenylethyl)acetamide (83303-96-2)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

4-chlorophenylacetic Acid (1878-66-6) + 4-Methoxyphenethylamine (55-81-2) → 2-(4-chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide (340218-64-6)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

p-chlorobenzyl cyanide (140-53-4) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With water; sodium hydroxide at 110 - 116℃; under 15001.5 Torr; for 0.05h; Concentration; Pressure; Temperature; Flow reactor;	99%
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.1h; Green chemistry;	96%
With potassium hydroxide In toluene at 160℃; for 0.5h; microwave irradiation;	92%

4-chloro-benzeneacetic acid, ethyl ester (14062-24-9) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	98%

carbon monoxide (201230-82-2) + 4-chlorobenzyl bromide (622-95-7) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 60℃; under 760 Torr; for 18h; Carbonylation;	95%
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Temperature; Reagent/catalyst; Autoclave;	95.2%
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;	79%
With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran at 55℃; for 3h;	78%

N-[(E)-2-(4-Chloro-phenyl)-1-cyano-vinyl]-4,N-dimethyl-benzamide (89244-19-9, 89244-20-2) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 6h; Heating;	95%

C14H21ClNO3P → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogen bromide at 100℃; for 0.166667h;	95%
With water; hydrogen bromide at 100℃; for 0.166667h; Inert atmosphere;	95%

4-Methoxybenzyl 2-(4-chlorophenyl)acetate (1575722-27-8) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With proton-exchanged montmorillonite In dichloromethane at 20℃;	95%

2-(4-chlorophenyl)-1-(pyrrolidin-1-yl)-ethanone (19202-19-8) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 30h; Heating;	94%

1-Chloro-4-(chloromethyl)benzene (104-83-6) + butan-1-ol (71-36-3) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
Stage #1: butan-1-ol With cobalt(II) sulfate at 80℃; under 3750.38 Torr; for 4h; Autoclave; Stage #2: 1-Chloro-4-(chloromethyl)benzene With sodium hydroxide In water at 80℃; under 3750.38 Torr; for 24h; Concentration; Pressure; Temperature; Autoclave;	93.6%

carbon monoxide (201230-82-2) + 1-chloro-4-(dibromomethyl)benzene (62037-06-3) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With potassium hydroxide; dicobalt octacarbonyl; N-benzyl-N,N,N-triethylammonium chloride In benzene under 760 Torr; for 8h; Ambient temperature;	92%

(4-chloro-phenyl)-acetic acid methyl ester (52449-43-1) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	92%
With potassium hydroxide In methanol for 4h; Ambient temperature;	50%
With water for 36h;	50%

4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)phenylglycinonitrile → 4-chlorophenylacetic Acid (1878-66-6) + N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)amine (888963-33-5)

Conditions	Yield
With hydrogen bromide; acetic acid In dichloromethane; water at 20℃; for 1h;	A 92% B n/a

carbon monoxide (201230-82-2) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Temperature; Reagent/catalyst; Solvent; Autoclave;	90%
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry; Stage #2: 1-Chloro-4-(chloromethyl)benzene With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction;	86%
With bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; under 11251.1 Torr; for 20h; Autoclave; regioselective reaction;	86%
With sodium hydroxide; cerium(III) chloride; cetyltrimethylammonim bromide; nickel cyanide In toluene at 85 - 95℃; under 1 Torr; for 6.5h;	82%
With water; palladium diacetate at 110℃; under 37503.8 Torr; for 4h; Ionic liquid;	84 %Chromat.

2-(4-chlorophenyl)-1-(morpholin-4-yl)-ethanethione (42945-85-7) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide for 0.0166667h; microwave irradiation;	90%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 100℃; for 8h;

1-Chloro-4-(chloromethyl)benzene (104-83-6) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With sodium hydroxide; cobalt tetracarbonyl anion In methanol at 55℃; for 4h;	84%
Multi-step reaction with 2 steps 1: dimethylsulfoxide / 5 h / 45 - 50 °C 2: KOH / aq. ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: alcohol / 120 - 130 °C / im Druckrohr 2: concentrated KOH-solution View Scheme
Multi-step reaction with 2 steps 1: alcohol; water 2: concentrated KOH-solution View Scheme
Multi-step reaction with 2 steps 1: ethanol; H2O / Heating 2: aq. KOH / ethanol / Heating View Scheme

carbon dioxide (124-38-9) + (4-chlorobenzylidene)hydrazine (52372-80-2) → 4-chlorophenylacetic Acid (1878-66-6)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	82%

4-vinylbenzyl chloride (1073-67-2) → 4-chlorophenylacetic Acid (1878-66-6)

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 
• 1197-55-3 4-aminophenylacetic acid 
• 15601-44-2 (Z/E)-4-(4-chlorobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one 
• 140-53-4 p-chlorobenzyl cyanide 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 
• 201230-82-2 carbon monoxide 
• 622-95-7 4-chlorobenzyl bromide 
• 58784-40-0 4-chlorophenyl isocyanate 
• 4251-65-4 (4-chlorophenyl)acetaldehyde 
• 103-82-2 phenylacetic acid 
• 7782-50-5 chlorine 
• 56-23-5 tetrachloromethane 

Downstream Products

• 109286-41-1 8-(4-chloro-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 5586-88-9 1-(4-chlorophenyl)propan-2-one 
• 18951-46-7 (E)-4-<2-(4-chlorophenyl)ethenyl>phenol 
• 10465-91-5 3-(4-chlorophenyl)-2H-chromen-2-one 
• 71512-20-4 2-(4-chlorophenyl)-N-phenylacetamide 
• 68557-33-5 2'-phenyl-(4-chlorophenyl)acetohydrazide 
• 10268-55-0 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-chlorophenyl)-acetamide 
• 138356-76-0 2-(4-Chloro-phenyl)-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-acetamide 
• 55138-47-1 (E)-2-(4-Chloro-phenyl)-3-furan-2-yl-acrylic acid 
• 55138-48-2 (Z)-2-(4-Chloro-phenyl)-3-furan-2-yl-acrylic acid 
• 50626-16-9 (E)-2-(4-Chloro-phenyl)-3-thiophen-2-yl-acrylic acid 
• 75581-01-0 4-(4-chlorobenzylidene)-2,2,6,6-tetramethyl-3,5-dioxa-2,6-disilaheptane 
• 17293-69-5 methyl 2-(4-chlorophenyl)ethanethionate 
• 127063-63-2 4-[(E)-2-(4-Chloro-phenyl)-vinyl]-2,6-dimethyl-phenol 

Relevant articles and documents

Asymmetric Catalytic Alkylation of 4-Chlorophenylacetic Acid

Using N-(monoalkyl)-α,β-diphenyl-β-hydroxy ethylamine as chiral ligands, 46.2percent enantiomeric excess was obtained in the asymmetric catalytic alkylation of 4-chlorophenylacetic acid.

Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst

A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.

Desulfonylative Electrocarboxylation with Carbon Dioxide

Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.

Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.