774-74-3

Basic information

• Product Name: 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE
• Synonyms: 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE;Acetyl chloride, (2,4-dichlorophenoxy)-;2,4-Dichlorophenoxyacetic acid chloride;Acetyl chloride, 2-(2,4-dichlorophenoxy)-
• CAS NO: 774-74-3
• Molecular Formula: C₈H₅Cl₃O₂
• Molecular Weight: 239.4831
• EINECS: 212-268-8
• Mol File: 774-74-3.mol
• Article Data: 61

Chemical Properties

• Boiling Point: 296.4 °C at 760 mmHg
• Flash Point: 126.3 °C
• Appearance: /
• Density: 1.475 g/cm³
• Vapor Pressure: 0.00168mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE(774-74-3)
• EPA Substance Registry System: 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE(774-74-3)

Safety Data

• Hazardous Substances Data: 774-74-3(Hazardous Substances Data)

Usage

General Description

2-(2,6-Dichlorophenoxy)acetyl chloride is a chemical compound with the molecular formula C10H7Cl3O2. It is a chlorinated acetic acid derivative and is commonly used in the synthesis of herbicides and other agrochemicals. 2-(2,6-DICHLOROPHENOXY)ACETYL CHLORIDE is reactive and may present health hazards if not handled properly. It is also used in the production of pharmaceuticals and dyes. The acetyl chloride group in the compound makes it highly reactive with nucleophiles, allowing for a wide range of applications in organic synthesis. Due to its reactivity and potential health risks, proper precautions should be taken when handling and using 2-(2,6-Dichlorophenoxy)acetyl chloride.

InChI:InChI=1/C8H5Cl3O2/c9-5-2-1-3-6(10)8(5)13-4-7(11)12/h1-3H,4H2

Synthetic route

2,4-Dichlorophenoxyacetic acid (94-75-7) → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
With thionyl chloride at 100℃; for 5h; Substitution;	100%
With thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride In chloroform for 4h; Chlorination; Heating;	85%
With thionyl chloride at 75℃; for 2h;	80%

2,4-dichlorophenol (120-83-2) → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / NaOH / H2O / 3 h / 110 - 120 °C 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: 33percent aq. NaOH / 1 h / Heating 2: SOCl2 / CHCl3 / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: aq. NaOH / 0.5 h / Heating 2: SOCl2 / benzene; ethyl acetate / 6 h / Heating View Scheme

2,4-dichlorophenol (120-83-2) + sodium-salt of/the/ 3-formyl-benzenesulfonic acid → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + silver-salt of/the/ <2,4-dichloro-phenoxy>-acetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: K2CO3; KI; PEG-600 / toluene / 1.5 h / 100 °C 1.2: 94 percent / HCl / H2O / 60 °C 2.1: 85 percent / SOCl2; benzyltriethylammonium chloride / CHCl3 / 4 h / Heating View Scheme

sodium 2,4-dichlorophenolate (3757-76-4) → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate 2: thionyl chloride / 8 h / Heating View Scheme

2,4-dichlorophenol (120-83-2) + (+-)-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / H2O / Heating 2: SOCl2 / ethyl acetate; methanol / 7 h / Heating View Scheme

5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl chloride → 2-hydroxyethyl 5-(2-chloro-4-trifluoromethyl phenoxy)-2-nitrobenzoate (77207-06-8) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
With triethylamine In dichloromethane; ethylene glycol

ethyl 2,4-dichlorophenoxyacetate (533-23-3) → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: thionyl chloride / Reflux View Scheme

methyl 2,4-dichlorophenoxyacetate (1928-38-7) → 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / methanol; water / 12 h / 50 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h / 20 °C View Scheme

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + p,p'-diaminobiphenyl (92-87-5) → 2-(2,4-dichloro-phenoxy)-N-{4'-[2-(2,4-dichloro-phenoxy)-acetylamino]-biphenyl-4-yl}-acetamide

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	99%

o-tolidin (119-93-7) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 2-(2,4-dichloro-phenoxy)-N-{4'-[2-(2,4-dichloro-phenoxy)-acetylamino]-3,3'-dimethyl-biphenyl-4-yl}-acetamide

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	98%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + 1,4-phenylenediamine (106-50-3) → 2-(2,4-dichloro-phenoxy)-N-{4-[2-(2,4-dichloro-phenoxy)-acetylamino]-phenyl}-acetamide

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	98%

1,2-diamino-benzene (95-54-5) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 2-(2,4-dichloro-phenoxy)-N-{2-[2-(2,4-dichloro-phenoxy)-acetylamino]-phenyl}-acetamide

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	96%

dimethyl (1-hydroxyethyl)phosphonate (10184-66-4) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (215655-76-8)

Conditions	Yield
With dmap; triethylamine In chloroform; toluene at -40 - -30℃; for 4h; Temperature; Solvent; Reagent/catalyst; Autoclave; Large scale;	95.8%
With organic base In chloroform at 20 - 40℃; for 5h;	90.7%
With pyridine In chloroform at 10 - 42℃;	89%

(Z)-2-chloro-N'-hydroxyethanimidamide (3272-96-6) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → O-(2,4-dichlorophenoxy)acetylchloroacetamidoxime (31912-19-3)

Conditions	Yield
With triethylamine In toluene	95.1%

6-hydroxy-4'-methylaurone + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 6-(2,4-dichlorophenoxyacetoxy)-4'-methylaurone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	94.6%

2-(N,N-dimethylamino)ethanol (108-01-0) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → (2,4-dichloro-phenoxy)-acetic acid-(2-dimethylamino-ethyl ester); hydrochloride (64046-52-2)

Conditions	Yield
In chloroform	94%
With chloroform
With benzene

hydroquinone (123-31-9) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → (2,4-Dichloro-phenoxy)-acetic acid 4-[2-(2,4-dichloro-phenoxy)-acetoxy]-phenyl ester

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	93%

6-amino-4-methyl-2-(4-morpholinyl)quinoline (656243-32-2) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 2-(2,4-dichloro-phenoxy)-N-(4-methyl-2-morpholin-4-yl-quinolin-6-yl)-acetamide

Conditions	Yield
In dichloromethane for 3h;	93%

1,6-Hexanediamine (124-09-4) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 2-(2,4-dichloro-phenoxy)-N-{6-[2-(2,4-dichloro-phenoxy)-acetylamino]-hexyl}-acetamide

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	92%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + 2,4-dichlorophenoxyacetylhydrazine (28236-62-6) → 2-(2,4-dichlorophenoxy)-N'-(2-(2,4-dichlorophenoxy)acetyl)acetohydrazide

Conditions	Yield
In tetrahydrofuran for 0.166667h; Time; Reagent/catalyst; Temperature; Microwave irradiation;	92%

3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)propenone (142531-17-7) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 4'-(2,4-dichlorophenoxyacetoxy)-2,4-dichlorochalcone

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 12h;	91.5%

6-hydroxy-4'-methoxylaurone (20727-61-1) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 6-(2,4-dichlorophenoxyacetoxy)-4'-methoxylaurone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	91.2%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + 3-methyl-2,4-decadienyl alcohol → 3-methyl-2ξ,4E-decadienyl (2,4-dichlorophenoxy)acetate

Conditions	Yield
In benzene for 0.5h;	91%

dimethyl α-hydroxy-α-(2-thienyl)methanephosphonate (98335-90-1) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(thien-2-yl)methylphosphonate

Conditions	Yield
In chloroform	91%
With organic base In chloroform at 20 - 40℃; for 5h;	86.2%
With pyridine In dichloromethane at 5℃; for 4h;
With pyridine In dichloromethane at 5℃; for 4h;

4-hydroxy-3-ethoxybenzaldehyde (121-32-4) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → C17H14Cl2O5 (933675-45-7)

Conditions	Yield
With pyridine In benzene at 20 - 23℃;	91%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + diethyl malonate (105-53-3) → diethyl-2',4'-dichloro-phenoxy-acetyl-malonate

Conditions	Yield
With hydrogenchloride; magnesium chloride; triethylamine In acetonitrile	91%

6-hydroxy-4'-dimethylaminoaurone (637753-80-1) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 6-(2,4-dichlorophenoxyacetoxy)-4'-dimethylaminoaurone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	90.8%

2-benzylidene-6-hydroxybenzofuran-3(2H)-one (4940-56-1) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 6-(2,4-dichlorophenoxyacetoxy)aurone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	90.1%

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → (2,4-Dichloro-phenoxy)-acetic acid 6-hydroxymethyl-4-oxo-4H-pyran-3-yl ester (128998-08-3)

Conditions	Yield
With sodium hydroxide In water; acetone for 2h; Ambient temperature;	90%

1,7,7-trimethyl-bicyclo[2.2.1]heptane-2-one-oxime (37939-80-3) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → C18H21NCl2O3

Conditions	Yield
With pyridine In benzene at 20 - 23℃;	90%

C10H22N2O + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → N-(2-dimethylaminoethyl)-N-(trans-2-hydroxycyclohexyl)-2,4-dichlorophenoxyacetamide

Conditions	Yield
With sodium hydroxide In water; benzene	90%

2-(3,4-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one (32396-83-1) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 6-(2,4-dichlorophenoxyacetoxy)-3',4'-dimethoxyaurone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	89.4%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + 5-Phenoxymethyl-3H-[1,3,4]oxadiazol-2-one (77052-40-5) → 3-[2-(2,4-Dichloro-phenoxy)-acetyl]-5-phenoxymethyl-3H-[1,3,4]oxadiazol-2-one

Conditions	Yield
for 0.5h;	89%

Diethyl-α-hydroxyethylphosphinoxid (30343-16-9) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → C14H19Cl2O4P

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	89%

3-(furan-2-yl)-1-pyrimidin-1H-pyrazol-5-amine + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → 2-(2,4-dichlorophenoxy)-N-(3-(furan-2-yl)-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)acetamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	88.96%

2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) + O,O-dimethyl-1-hydroxy-1-(pyridin-2-yl)methylphosphonate → O,O-dimethyl 1-[(2,4-dichlorophenoxy)acetoxy]-1-(pyridin-2-yl)methylphosphonate (845899-06-1)

Conditions	Yield
With triethylamine In chloroform at 0 - 40℃;	88%
With organic base In chloroform at 20 - 40℃; for 5h;	82.5%

dimethyl(furan-2-yl(hydroxy)methyl)phosphonate (1883-27-8) + 2-(2,4-dichlorophenoxy)acetyl chloride (774-74-3) → O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(furan-2-yl)methylphosphonate (263722-89-0)

Conditions	Yield
In chloroform	87%
With organic base In chloroform at 20 - 40℃; for 5h;	81.4%

Upstream product

• 1928-38-7 methyl 2,4-dichlorophenoxyacetate 
• 533-23-3 ethyl 2,4-dichlorophenoxyacetate 
• 120-83-2 2,4-dichlorophenol 
• 3757-76-4 sodium 2,4-dichlorophenolate 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 

Downstream Products

• 21443-42-5 1-diazo-3-(2,4-dichloro-phenoxy)-propan-2-one 
• 128998-08-3 (2,4-Dichloro-phenoxy)-acetic acid 6-hydroxymethyl-4-oxo-4H-pyran-3-yl ester 
• 83143-98-0 2,4-dichlorophenoxymethyl 2,4-dichlorophenoxyacetate 
• 50648-98-1 1-[(2,4-dichloro-phenoxy)-acetyl]-DL-proline 
• 50648-98-1 1-[(2,4-dichloro-phenoxy)-acetyl]-L-proline 
• 98556-40-2 2-(2,4-dichlorophenoxy)ethenone ketene 
• 5253-45-2 2,4-dichlorophenyl 2,4-dichlorophenoxyacetate 
• 5253-44-1 (2,4-dichloro-phenoxy)-acetic acid phenyl ester 
• 80913-70-8 N-[(2,4-dichloro-phenoxy)-acetyl]-DL-serine 
• 72836-61-4 (2,4-dichloro-phenoxy)-acetic acid-(2-diethylamino-ethyl ester); hydrochloride 
• 17186-73-1 2-[(2,4-dichloro-phenoxy)-acetoxy]-benzoic acid 
• 109037-66-3 (2,4-dichloro-phenoxy)-acetic acid-[5-(4-nitro-phenoxy)-pentylamide] 
• 10441-30-2 (2,4-dichloro-phenoxy)-acetic acid-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethylamide] 
• 109598-88-1 N-[(2,4-dichloro-phenoxy)-acetyl]-N-p-tolyl-glycine 

Relevant articles and documents

Direct electrochemical oxidation of a pesticide, 2,4-dichlorophenoxyacetic acid, at the surface of a graphite felt electrode: Biodegradability improvement

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