6575-24-2

Basic information

• Product Name: 2,6-Dichlorophenylacetic acid
• Synonyms: RARECHEM AL BO 0115;TIMTEC-BB SBB003503;2-(2,6-DICHLOROPHENYL)ACETIC ACID;2,6-DICHLORO BENZENEACETIC ACID;2,6-DICHLOROPHENYLACETIC ACID;Benzeneacetic acid, 2,6-dichloro-;2,6-Dichlorophenyl acetic acid 98%;2,6-Dichlorophenylacetic acid, 98+%
• CAS NO: 6575-24-2
• Molecular Formula: C₈H₆Cl₂O₂
• Molecular Weight: 205.04
• EINECS: 229-504-0
• Product Categories: Acids and Derivatives;Aromatic Phenylacetic Acids and Derivatives;Phenylacetic acid;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 6575-24-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 159-162 °C
• Boiling Point: 294.45°C (rough estimate)
• Flash Point: 150.5 °C
• Appearance: white crystalline powder
• Density: 1.3806 (rough estimate)
• Vapor Pressure: 9.54E-05mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.80±0.10(Predicted)
• BRN: 1952744
• CAS DataBase Reference: 2,6-Dichlorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichlorophenylacetic acid(6575-24-2)
• EPA Substance Registry System: 2,6-Dichlorophenylacetic acid(6575-24-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-26/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 6575-24-2(Hazardous Substances Data)

Usage

Uses

2,6-Dichlorophenylacetic acid is an inhibitor of isopenicillin N synthase (IPNS) and acyl-CoA: 6-APA acyltransferase. 2,6-Dichlorophenylacetic acid is also part of a group of phenylacetate derivatives that have cytostatic activity against tumour cells.

Chemical Properties

white crystalline powder

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

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

Downstream Products

• 1450833-50-7 C₁₈H₂₆Cl₂N₂O₅ 
• 116316-58-6 1-chloro-3-(2,6-dichlorophenyl)propan-2-one 
• 46999-59-1 N''-[2-(2,6-Dichloro-phenyl)-acetyl]-N,N,N',N'-tetramethyl-guanidine 
• 29110-50-7 N-(2,6-dichlorophenyl)acetyl-S-methylisothiourea 
• 125334-49-8 3-(2,6-dichlorophenyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione 
• 138914-79-1 methyl 2-chloro-6-(4-methoxycarbonylphenoxy)phenylacetate 
• 138914-71-3 methyl 2-chloro-6-(4-methoxyphenoxy)phenylacetate 
• 138914-80-4 2-chloro-(4-carboxyphenoxy)phenylacetic acid 
• 138914-72-4 2-chloro-6-(4-methoxyphenoxy)phenyl acetic acid 

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