6575-24-2

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichlorophenylacetic acid is used as an enzyme inhibitor for isopenicillin N synthase (IPNS) and acyl-CoA: 6-APA acyltransferase, playing a crucial role in the synthesis of certain antibiotics.
Used in Oncology:
2,6-Dichlorophenylacetic acid is used as a cytostatic agent for its activity against tumor cells. It is particularly effective in inhibiting the growth of cancer cells, making it a valuable compound in the development of cancer treatments.
Used in Chemical Research:
Due to its unique chemical properties and enzyme-inhibiting capabilities, 2,6-Dichlorophenylacetic acid is also used as a research compound in various scientific studies, contributing to the advancement of knowledge in biochemistry and pharmacology.

Purification Methods

Crystallise the acid from aqueous EtOH. [Beilstein 9 III 2272.]

InChI:InChI=1/C8H6Cl2O2/c9-6-2-1-3-7(10)5(6)4-8(11)12/h1-3H,4H2,(H,11,12)/p-1

Synthetic route

2,2,6,6-tetrachlorocyclohexanone (3776-30-5) + diethyl malonate (105-53-3) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Stage #1: 2,2,6,6-tetrachlorocyclohexanone; diethyl malonate With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dichloro-ethane at 60 - 65℃; for 3h; Stage #2: With sodium hydroxide In 1,2-dichloro-ethane at 20 - 65℃; for 3h; Solvent; Temperature; Reagent/catalyst;	96.6%

ethyl 2-(2,6-dichlorophenyl)acetate (90793-64-9) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	95%

carbon monoxide (201230-82-2) + 1,3-Dichloro-2-chloromethyl-benzene (2014-83-7) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
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;	93%

2,6-dichlorophenylacetonitrile (3215-64-3) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Stage #1: 2,6-dichlorophenylacetonitrile With potassium hydroxide; water In ethanol at 80℃; for 20h; Stage #2: With hydrogenchloride In ethanol pH=3;	83%
With sodium hydroxide
With potassium hydroxide In ethylene glycol

etheric 2.6-dichloro-benzyl magnesium chloride → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Einleiten von Kohlendioxid;

carbon dioxide (124-38-9) + 2,6-dichlorotoluene (118-69-4) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Stage #1: 2,6-dichlorotoluene With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -75℃; for 0.75h; Stage #2: carbon dioxide In tetrahydrofuran; cyclohexane

carbon dioxide (124-38-9) + 2,6-dichlorotoluene (118-69-4) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 3,5-dichloro-4-methylbenzoic acid (39652-34-1) + 2,4-Dichloro-3-methyl-benzoic acid (83277-23-0)

Conditions	Yield
Stage #1: 2,6-dichlorotoluene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -75℃; for 0.75h; Stage #2: carbon dioxide In tetrahydrofuran; cyclohexane Title compound not separated from byproducts;

1,3-Dichloro-2-chloromethyl-benzene (2014-83-7) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylsulfoxide / 5 h / 40 - 50 °C 2: 25 percent NaOH / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 2: H2SO4 View Scheme

2,6-dichlorotoluene (118-69-4) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 View Scheme

2,6-Dichloroaniline (608-31-1) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite; sulfuric acid; copper(I) bromide; tetrabutylammomium bromide / water / 2 h / -5 - 95 °C 2: hydrogenchloride / 10 h / 80 - 95 °C / Inert atmosphere View Scheme

1-(2,2,2-trichloroethyl)-2,6-dichlorobenzene (30359-34-3) → 2-(2,6-dichlorophenyl)acetic acid (6575-24-2)

Conditions	Yield
With hydrogenchloride at 80 - 95℃; for 10h; Inert atmosphere;	115.3 g

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2,6-dichlorophenylacetylchloride (61875-53-4)

Conditions	Yield
With thionyl chloride In toluene at 20℃; for 12h;	100%
With thionyl chloride at 80℃; for 1h;	90%
With thionyl chloride

thionyl chloride (7719-09-7) + 2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 1-bromo-3-(2,6-dichlorophenyl)propan-2-one (880089-70-3)

Conditions	Yield
Stage #1: thionyl chloride; 2-(2,6-dichlorophenyl)acetic acid With diazomethyl-trimethyl-silane Stage #2: With hydrogen bromide In water	100%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2-(2,6-dichlorophenyl)(1,1-2H2)ethan-1-ol

Conditions	Yield
With borane-d3 In tetrahydrofuran at 0 - 20℃; for 20h;	99%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 4-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol → 1-[(1S,3R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(3-hydroxy-3-methylbutyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-(2,6-dichlorophenyl)ethanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran	98%
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 1h; Stage #2: 4-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol In tetrahydrofuran at 45℃; for 24h; Reagent/catalyst;	376 g
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 1h; Stage #2: 4-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol In tetrahydrofuran at 25 - 45℃; for 24h;	376 g
With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 40℃; for 72h; Inert atmosphere;	250 mg

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2-(2,6-dichlorophenyl)ethan-1-ol (30595-79-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 12h; Heating;	97%
With lithium aluminium tetrahydride In diethyl ether for 16h; Heating / reflux;	85%
With borane In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	73%
With lithium aluminium tetrahydride In diethyl ether
With borane In tetrahydrofuran

endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2) + 2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2,6-Dichloro-benzoic acid (1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide	97%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2-(2,6-dichlorophenyl)(2H2)acetic acid

Conditions	Yield
With deuteriated sodium hydroxide; tetrabutylammomium bromide In water-d2 at 105℃; for 40h;	97%

methanol (67-56-1) + 2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → methyl 2-(2,6-dichlorophenyl)acetate (54551-83-6)

Conditions	Yield
With sulfuric acid	96%
With hydrogenchloride Reflux;	92%
With thionyl chloride at 0℃; Reflux;	10 g
With sulfuric acid for 8h; Reflux;

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + ethyl 4-(piperazin-1-yl)benzoate (80518-57-6) → C21H22Cl2N2O3 (1092069-59-4)

Conditions	Yield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	95%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + (1S,3R)-5-bromo-3-(((tertbutyldiphenylsilyl) oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline → 1-[(1S,3R)-5-bromo-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2,6-dichlorophenyl)ethanone

Conditions	Yield
Stage #1: 2-(2,6-dichlorophenyl)acetic acid; (1S,3R)-5-bromo-3-(((tertbutyldiphenylsilyl) oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline With trimethylamine In acetonitrile for 0.0833333h; Stage #2: With propylphosphonic anhydride In ethyl acetate; acetonitrile at 5 - 20℃; for 1.25h;	93%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2-(2,6-dichlorophenyl)acetohydrazide (129564-34-7)

Conditions	Yield
With 1,1'-carbonyldiimidazole; hydrazine In tetrahydrofuran	92%
With 1,1'-carbonyldiimidazole; hydrazine In tetrahydrofuran	92%
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran Stage #2: With hydrazine In tetrahydrofuran Further stages.;

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 1,2-diamino-benzene (95-54-5) → 2-(2,6-dichlorobenzyl)-1H-benzo[d]imidazole (743451-08-3)

Conditions	Yield
With polyphosphoric acid at 175℃; for 4h; Inert atmosphere;	92%
With polyphosphoric acid for 4h; Inert atmosphere; Heating;	92%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-2-(2,6-dichlorobenzyl)-1H-benzo[d]imidazole (1274937-60-8)

Conditions	Yield
With polyphosphoric acid for 4h; Inert atmosphere; Heating;	92%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2,6-dichlorobenzaldehyde (83-38-5)

Conditions	Yield
With 1H-imidazole; C17H16ClMnN2O2; tetrabutylammonium periodite In chloroform at 20℃; for 0.666667h;	90%
With 1H-imidazole; [bis(acetoxy)iodo]benzene; Co(AAOPD) In acetonitrile at 20℃; for 6.33333h;	89%
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;	76%
With oxygen; mercury(II) oxide In methanol; acetonitrile at 25℃; UV-irradiation;	64%
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;	12.5 %Chromat.

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 2,6-Dichlorobenzyl bromide (20443-98-5)

Conditions	Yield
With silver triflate-bis(1,10-phenanthroline) complex; dibromoisocyanuric acid In 1,2-dichloro-ethane at 20℃; for 22h; Inert atmosphere; Schlenk technique;	88%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + (1S)-5-bromo-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride → 1-[(1S)-5-bromo-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-(2,6-dichlorophenyl)ethanone

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	86%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 1,3-Dichloro-2-chloromethyl-benzene (2014-83-7)

Conditions	Yield
With tert-butylhypochlorite; silver triflate-bis(1,10-phenanthroline) complex In acetonitrile at 20℃; for 26h; Inert atmosphere;	85%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 4-[(1S,3R)-3-(hydroxymethyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol → 2-(2,6-dichlorophenyl)-1-((1S,3R)-5-(3-hydroxy-3-methylbutyl)-3-(hydroxymethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Conditions	Yield
Stage #1: 4-[(1S,3R)-3-(hydroxymethyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In acetonitrile at 0℃; for 0.5h; Stage #2: 2-(2,6-dichlorophenyl)acetic acid In acetonitrile at 0℃; for 1h;	85%
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In acetonitrile at 0℃; for 1h; Stage #2: 4-[(1S,3R)-3-(hydroxymethyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol With potassium carbonate In water; acetonitrile at 0℃; for 4h; Solvent;	85%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 2-fluoro-6-[(4,6-dimethoxy-1,3,5-triazin-2-yl)methyl]benzenamine → 2-(2,6-dichlorophenyl)-N-{2-fluoro-6-[(4,6-dimethoxy-1,3,5-triazin-2-yl)methyl]phenyl}acetamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 20℃; for 2h; Alkaline conditions;	85%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + (1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline → 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 2h;	84%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + (1S,3R)-5-bromo-3-(([tert-butyl(dimethyl)silyl]oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline → 1-[(1S,3R)-5-bromo-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2,6-dichlorophenyl)ethan-1-one

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide	83%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	55%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	4.70 g
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	4.7 g

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 2-(2,6-dichloro-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide (318294-29-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Condensation; Heating;	82%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 4-amino-N-(4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide → 4-(2-(2,6-dichlorophenyl)acetamido)-N-(4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	81%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + benzylamine (100-46-9) → 1-benzyl-4-chloro-1,3-dihydroindol-2-one (849098-26-6)

Conditions	Yield
Stage #1: 2-(2,6-dichlorophenyl)acetic acid; benzylamine at 150℃; for 0.5h; microwave irradiation; Stage #2: With sodium hydroxide; XPhos; palladium diacetate In water; toluene at 100℃; for 0.5h; microwave irradiation;	80%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + β-(3-chlorobenzyl)mercaptoethylamine (106670-33-1) → N-[2-(3-chlorobenzylsulfanyl)ethyl]-2-(2,6-dichlorophenyl)acetamide (1234381-00-0)

Conditions	Yield
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Inert atmosphere; Stage #2: β-(3-chlorobenzyl)mercaptoethylamine With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	80%
Stage #1: 2-(2,6-dichlorophenyl)acetic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Inert atmosphere; Stage #2: β-(3-chlorobenzyl)mercaptoethylamine With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	80%

2-(2,6-dichlorophenyl)acetic acid (6575-24-2) + 4-(4-aminobenzyl)-5-(dibromomethylene)furan-2(5H)-one → N-(4-((2-(dibromomethylene)-5-oxo-2,5-dihydrofuran-3-yl)methyl)phenyl)-2-(2,6-dichlorophenyl)acetamide

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	78%

Upstream product

• 3215-64-3 2,6-dichlorophenylacetonitrile 
• 124-38-9 carbon dioxide 
• 118-69-4 2,6-dichlorotoluene 
• 608-31-1 2,6-Dichloroaniline 
• 30359-34-3 1-(2,2,2-trichloroethyl)-2,6-dichlorobenzene 
• 3776-30-5 2,2,6,6-tetrachlorocyclohexanone 
• 105-53-3 diethyl malonate 
• 201230-82-2 carbon monoxide 
• 2014-83-7 1,3-Dichloro-2-chloromethyl-benzene 
• 90793-64-9 ethyl 2-(2,6-dichlorophenyl)acetate 

Downstream Products

• 84279-12-9 2-(2,6-Dichloro-phenyl)-N-[6-(2,6-dichloro-phenyl)-2-methyl-pyrido[2,3-d]pyrimidin-7-yl]-acetamide 
• 90793-64-9 ethyl 2-(2,6-dichlorophenyl)acetate 
• 221121-34-2 (2,6-dichlorophenylacetyl)imidazolide 
• 29110-47-2 guanfacine 
• 2012-78-4 2-(2,6-dichlorophenyl)propionic acid 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 129564-34-7 2-(2,6-dichlorophenyl)acetohydrazide 

Relevant academic research and scientific papers

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The present invention is directed to compounds useful for the regulation of cholesterol of Formula I, methods for using them and pharmaceutical compositions thereof, STR1 wherein X and Y are oxygen, sulfur, or (CR'R")n wherein n is 1 to 4; R is hydrogen, alkyl, or benzyl; R1 and R2 are phenyl, substituted phenyl, naphthyl, substituted naphthyl, an aralkyl group, an alkyl chain, adamantyl, or a cycloalkyl group.

METABOLISM OF CHLOROPHENYLALANINES IN CROP AND WEED PLANTS IN RELATION TO THE FORMATION OF POTENTIAL HERBICIDAL END PRODUCTS

Metabolism of 12 synthetic D,L-chlorophenylalanines has been examined in several crop and weed plants.Twenty-five gram samples of excised shoots or leaves of bushbean, soybean, corn, pigweed, lambsquarters, and giant foxtail were allowed to metabolize 10-4 M solutions of the D,L-chlorophenylalanines for 24 hr in continuous light.The plant samples were then extracted in 80percent methanol and the soluble acidic metabolites fractionated into ether.Each ether concentrate was partially purified by fractional elution from a PrepSep C18 coloumn and then analysed by HPLC.Collected fractions were esterified with pentafluorobenzylbromide and examined by GC-MS to demonstrate the presence of PFB-esters of chlorophenylacetic, chlorobenzoic and/or chlorocinnamic acids.Since certain of these metabolites are known to be potent plant growth-regulators and herbicides, the results are discussed in relation to the potantial herbicidal action of certain chlorophenylalanines by the mechanism of 'lethal synthesis'.Key Word Index - Phaseolus vulgaris; Glycine max.; Leguminosae; Zea mays; Amaranthus retroflexus; Chenopodium album; Setaria faberii; metabolism; D,L-chlorophenylalanines; chlorophenylacetic acids; chlorobenzoic acids; chlorocinnamic acids; growth regulators.