41022-54-2

Basic information

• Product Name: ETHYL 2,4-DICHLOROPHENYL ACETATE
• Synonyms: BUTTPARK 37\11-71;ETHYL 2,4-DICHLOROPHENYL ACETATE;(2,4-DICHLORO-PHENYL)-ACETIC ACID ETHYL ESTER;2-(2,4-dichlorophenyl)acetic acid ethyl ester;ethyl 2-(2,4-dichlorophenyl)ethanoate;2,4-Dichlorophenyl butyrate
• CAS NO: 41022-54-2
• Molecular Formula: C₁₀H₁₀Cl₂O₂
• Molecular Weight: 233.09
• EINECS: 1533716-785-6
• Mol File: 41022-54-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 88/0.05mm
• Flash Point: 121.8 °C
• Appearance: /
• Density: 1.266 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL 2,4-DICHLOROPHENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,4-DICHLOROPHENYL ACETATE(41022-54-2)
• EPA Substance Registry System: ETHYL 2,4-DICHLOROPHENYL ACETATE(41022-54-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 41022-54-2(Hazardous Substances Data)

Usage

General Description

ETHYL 2,4-DICHLOROPHENYL ACETATE is a chemical compound that belongs to the class of organic compounds known as phenyl acetates. It is composed of a phenyl group with two chlorine atoms attached to the benzene ring, and an acetate group attached to the benzene ring, making it a derivative of acetic acid. ETHYL 2,4-DICHLOROPHENYL ACETATE is commonly used in the synthesis of pharmaceuticals and agrochemicals. It is also used as a flavoring agent and fragrance ingredient in the manufacture of cosmetics and personal care products.ETHYL 2,4-DICHLOROPHENYL ACETATE is an important intermediate in organic synthesis and has various industrial applications.

Synthetic route

ethanol (64-17-5) + 2,4-dichlorophenylacetic acid (19719-28-9) → ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2)

Conditions	Yield
With sulfuric acid In benzene	95%
With sulfuric acid In benzene Reflux;

4-chloro-benzeneacetic acid, ethyl ester (14062-24-9) → ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2)

Conditions	Yield
With sodium persulfate; N-chloro-succinimide; trifluorormethanesulfonic acid; palladium diacetate In 1,2-dichloro-ethane at 70℃; for 7h; Sealed tube; regioselective reaction;	66%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + 2,4-dichlorobenzyl mercaptan (59293-67-3) → ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2)

Conditions	Yield
With dicobalt octacarbonyl; water at 190℃; under 43957.6 - 46543.3 Torr; for 24h;	25%

ethyl α-bromo-2,4-dichlorophenylacetate (41022-55-3) → ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + 2,3-Bis-(2,4-dichloro-phenyl)-succinic acid diethyl ester (129430-58-6, 129430-59-7)

Conditions	Yield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → ethyl α-bromo-2,4-dichlorophenylacetate (41022-55-3)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane for 5h; Irradiation;	98.7%

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + Diethyl carbonate (105-58-8) → diethyl 2-(2,4-dichlorophenyl)propanedioate (111544-93-5)

Conditions	Yield
With sodium hydride In toluene at 20 - 100℃; for 1h; Inert atmosphere;	78%

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + nitrobenzene (98-95-3) → (2,4-dichlorophenyl)(4-nitrophenyl)methanone (855194-85-3)

Conditions	Yield
With potassium tert-butylate In benzene at 20℃; regiospecific reaction;	68%

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 5-hydroxy-2,4,6-tris(2,4-dichlorophenyl)-1,3-phenylene bis(dihydrogen phosphate) + 2,4,6-tris(2,4-dichlorophenyl)benzene-1,3,5-triyl tris(dihydrogen phosphate)

Conditions	Yield
With phosphorus pentoxide at 130℃; for 0.833333h;	A 64% B 10%
With pyrophosphoric acid at 130℃; for 0.833333h;	A n/a B 64%
With phosphorus pentoxide at 130℃; for 0.916667h;	A 52% B 16%
With pyrophosphoric acid at 130℃; for 0.833333h;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + ethyl trifluoroacetate, (383-63-1) → ethyl 2-(2,4-dichlorophenyl)-4,4,4-trifluoro-3-oxobutanoate

Conditions	Yield
With sodium In diethyl ether for 12h; Reflux;	7%

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + cinnamonitrile (4360-47-8) → 2-(2,4-dichlorophenyl)-4-cyano-3-phenylbutanoate d'ethyle threo (134823-36-2, 134823-37-3) + 2-(2,4-dichlorophenyl)-4-cyano-3-phenylbutanoate d'ethyle erythro (134823-36-2, 134823-37-3)

Conditions	Yield
With sodium amide 1.) Et2O, -5 deg C, 2.) a) Et2O, -5 deg C, 3 h, b) 15 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With sodium amide 1.) Et2O, -5 deg C, 2.) a) Et2O, -5 deg C, 3 h, b) 15 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2,3-Bis-(2,4-dichloro-phenyl)-succinic acid diethyl ester (129430-58-6, 129430-59-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98.7 percent / NBS / CCl4 / 5 h / Irradiation 2: dimethylformamide / Ambient temperature; electrolysis View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2-(2,4-Dichlorophenyl)-1-pyridin-4-yl-1-ethanone (902170-69-8)

Conditions	Yield
Stage #1: ethyl 2-(2, 4-dichlorophenyl)acetate With lithium diisopropyl amide In tetrahydrofuran at -60℃; for 0.333333h; Stage #2: ethyl 2-(2, 4-dichlorophenyl)acetate In tetrahydrofuran at 20℃; for 20h; Stage #3: With hydrogenchloride; sodium hydrogencarbonate more than 3 stages;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) + oxalic acid diethyl ester (95-92-1) → diethyl 2-(2,4-dichlorophenyl)-3-oxosuccinate (1188446-43-6)

Conditions	Yield
With sodium ethanolate In ethanol; mineral oil at 70℃; for 2h;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2,4-dichlorophenylacetylhydrazide

Conditions	Yield
With hydrazine hydrate In ethanol Reflux;
With hydrazine hydrate at 80℃; for 6h;

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2-mercapto-5-(2,4-dichlorobenzyl)-1,3,4-oxadiazole (1023575-67-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 6 h / 80 °C 2.1: carbon disulfide; potassium hydroxide / diethyl ether; ethanol / 16 h / 20 °C 2.2: 20 h / 65 °C View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 4-(2,4-dichlorophenyl)-1,2-tetramethylene-5-trifluoromethyl-4-pyrazolin-3-one

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium / diethyl ether / 12 h / Reflux 2: triethylamine / 1,4-dioxane / 2 h / Reflux View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → ethyl 3-(2,4-dichlorophenyl)-2-oxopropanoate (1188446-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol; mineral oil / 2 h / 70 °C 2: water; sodium chloride / dimethyl sulfoxide / 1 h / 120 °C View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → ethyl 5-(2,4-dichlorophenyl)-1,2,3-thiadiazole-4-carboxylate (1188446-46-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium ethanolate / ethanol; mineral oil / 2 h / 70 °C 2: water; sodium chloride / dimethyl sulfoxide / 1 h / 120 °C 3: toluene / 5 h / 100 °C 4: thionyl chloride / 18 h / 60 °C View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → ethyl 2-(3-(2,4-dichlorophenyl)-1-ethoxy-1-oxopropan-2-ylidene)hydrazinecarboxylate (1188446-45-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol; mineral oil / 2 h / 70 °C 2: water; sodium chloride / dimethyl sulfoxide / 1 h / 120 °C 3: toluene / 5 h / 100 °C View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2-(2,4-dichlorophenyl)propane-1,3-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / toluene / 1 h / 20 - 100 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Inert atmosphere View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl] methanesulfonate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / toluene / 1 h / 20 - 100 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Inert atmosphere 3: triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere View Scheme

ethyl 2-(2, 4-dichlorophenyl)acetate (41022-54-2) → 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-ylacetonitrile

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / toluene / 1 h / 20 - 100 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Inert atmosphere 3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 4.1: potassium hydroxide / dimethyl sulfoxide / 10 - 20 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere View Scheme

Upstream product

• 64-17-5 ethanol 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 41022-55-3 ethyl α-bromo-2,4-dichlorophenylacetate 
• 201230-82-2 carbon monoxide 
• 59293-67-3 2,4-dichlorobenzyl mercaptan 
• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 

Downstream Products

• 41022-55-3 ethyl α-bromo-2,4-dichlorophenylacetate 
• 129430-58-6 2,3-Bis-(2,4-dichloro-phenyl)-succinic acid diethyl ester 
• 902170-69-8 2-(2,4-Dichlorophenyl)-1-pyridin-4-yl-1-ethanone 
• 1188446-43-6 diethyl 2-(2,4-dichlorophenyl)-3-oxosuccinate 
• 1023575-67-8 2-mercapto-5-(2,4-dichlorobenzyl)-1,3,4-oxadiazole 
• 855194-85-3 (2,4-dichlorophenyl)(4-nitrophenyl)methanone 
• 1188446-44-7 ethyl 3-(2,4-dichlorophenyl)-2-oxopropanoate 
• 1188446-46-9 ethyl 5-(2,4-dichlorophenyl)-1,2,3-thiadiazole-4-carboxylate 
• 1188446-45-8 ethyl 2-(3-(2,4-dichlorophenyl)-1-ethoxy-1-oxopropan-2-ylidene)hydrazinecarboxylate 
• 111544-93-5 diethyl 2-(2,4-dichlorophenyl)propanedioate 
• 25173-21-1 2-(2,4-dichlorophenyl)propanoic acid 

Relevant articles and documents

2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists

A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.

Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors

A series of thiadiazole-based thioglycosides were synthesized as SGLT2 inhibitors from D-glucose, D-galactose and a variety of phenylacetic acids via a convenient protocol in 8 steps and evaluated in vivo with an oral glucose tolerance test (OGTT), and 5-benzyl-1,3,4-thiadiazol-2-yl 1-thio-β-D-glucopyranoside (1a) was the most efficacious to suppress the blood glucose excursion during OGTT.

Desulfurization and Carbonylation of Mercaptans

The first examples of the carbonylation of mercaptans are described: cobalt carbonyl catalyzes the desulfurization and carbonylation of mercaptans to carboxylic esters by means of carbon monoxide in aqueous alcohol.