2-(2-chloro-phenyl)-1-pyrrolidin-1-yl-ethanone
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 38h; Heating; | 98% |
2-chlorophenylacetic acid ethyl ester
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14; | 94% |
Conditions | Yield |
---|---|
Stage #1: butan-1-ol With cobalt(II) acetate; cobalt(II) nitrate at 40℃; under 3750.38 Torr; for 2h; Autoclave; Stage #2: 1-chloro-2-(chloromethyl)benzene With sodium hydroxide In water at 40℃; under 2250.23 Torr; for 12h; Concentration; Pressure; Temperature; Autoclave; | 93.7% |
carbon dioxide
1-chloro-2-(chloromethyl)benzene
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; manganese; palladium diacetate; magnesium chloride In N,N-dimethyl-formamide under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique; | 92% |
With (1,2-dimethoxyethane)dichloronickel(II); C15H27P*(x)BF4*H(1+); magnesium chloride; zinc In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; Schlenk technique; | 62% |
With samarium; chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; under 760.051 Torr; for 2h; Electrochemical reaction; Cooling with ice; | 42% |
Stage #1: 1-chloro-2-(chloromethyl)benzene With magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at 25℃; for 1h; Stage #2: carbon dioxide In tetrahydrofuran at 50℃; for 12h; | 272 mg |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate; trifluoroacetic acid In dichloromethane at 15 - 25℃; | 92% |
carbon monoxide
1-bromomethyl-2-chlorobenzene
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Autoclave; | 92% |
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave; | 70% |
carbon monoxide
1-chloro-2-(chloromethyl)benzene
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
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-2-(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; | 88% |
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Reagent/catalyst; Autoclave; | 88% |
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; | 85% |
With sodium hydroxide; cerium(III) chloride; cetyltrimethylammonim bromide; nickel cyanide In toluene at 85 - 95℃; under 1 Torr; for 6.5h; | 76% |
With water; palladium diacetate at 110℃; under 37503.8 Torr; for 4h; Ionic liquid; | 96 %Chromat. |
carbon dioxide
2-(2-chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h; | 57% |
formic acid
1-chloro-2-(chloromethyl)benzene
2'-chloro-benzeneacetic acid
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; | 50% |
1-Phenylethanol
2-(2-chlorophenyl)acetyl chloride
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
In diethyl ether | 47% |
carbon monoxide
2-chlorobenzal bromide
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With potassium hydroxide; dicobalt octacarbonyl; N-benzyl-N,N,N-triethylammonium chloride In benzene under 760 Torr; for 12h; Ambient temperature; | 34% |
2-(2-chlorophenyl)acetamide
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With cis-nitrous acid | |
(saponification); |
Conditions | Yield |
---|---|
With sulfuric acid | |
With potassium hydroxide | |
With potassium hydroxide In ethanol for 24h; Heating; |
4-(2-chlorobenzylidene)-2-phenyl-5-oxazolone
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
nachfolgend Oxydation mit Wasserstoffperoxyd; |
2-acetoxy-2-(2-chlorophenyl)acetic acid
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With Pd-BaSO4; tetralin |
carbon dioxide
(2-chloro-benzyl)-dimethyl-silane
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction; |
2-(2-chlorophenyl)malonic acid
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With AMDase; buffer solution at 15 - 35℃; Kinetics; ΔS(excit.), ΔH(excit.), ΔG(excit.); | |
With AMDase; buffer solution at 15℃; Rate constant; | |
With AMDase; buffer solution at 25℃; Rate constant; | |
With AMDase; buffer solution at 35℃; Rate constant; |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride for 0.5h; Heating; Yield given; |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide Behandlung mit Wasserstoffperoxyd; |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With sulfuric acid |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
at 0℃; Einleiten von Kohlendioxid; |
tetralin
2-acetoxy-2-(2-chlorophenyl)acetic acid
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
Hydrogenation; |
1-(2-chlorophenyl)-2-diazoethan-1-one
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With silver(l) oxide In 1,4-dioxane Rearrangement; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 99 percent / PPh3 / CH2Cl2 / 0.5 h / 0 °C 2: 96 percent / H2O / ethyl acetate / 8 h / 20 °C 3: 98 percent / aq. HCl / dioxane / 38 h / Heating View Scheme |
1-chloro-2-(2,2-dibromovinyl)benzene
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / H2O / ethyl acetate / 8 h / 20 °C 2: 98 percent / aq. HCl / dioxane / 38 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: aq. Ag2O / dioxane View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Heating; | 100% |
With ammonium cerium(IV) nitrate at 20℃; for 12h; | 99% |
sulfuric acid for 16h; Heating / reflux; | 97.5% |
2'-chloro-benzeneacetic acid
2-(2-chlorophenyl)acetyl chloride
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide In toluene | 100% |
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 0 - 25℃; for 1h; | 99% |
With phosphorus pentachloride |
2'-chloro-benzeneacetic acid
4-bromo-2-(2-(dimethylamino)ethoxy)aniline
N-(4-bromo-2-(2-(dimethylamino)ethoxy)phenyl)-2-(2-chlorophenyl)acetamide
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
2'-chloro-benzeneacetic acid
4-bromo-2-(2-methoxyethoxy)aniline
N-(4-bromo-2-(2-methoxyethoxy)phenyl)-2-(2-chlorophenyl)acetamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
2'-chloro-benzeneacetic acid
ethyl-3-benzylamino propionate
Conditions | Yield |
---|---|
Stage #1: 2'-chloro-benzeneacetic acid; ethyl-3-benzylamino propionate With dmap In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane | 99% |
Conditions | Yield |
---|---|
With pyridine; potassium tert-butylate for 12h; Heating; | 98.4% |
2'-chloro-benzeneacetic acid
Conditions | Yield |
---|---|
With nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid | 98% |
2'-chloro-benzeneacetic acid
ethanol
2-chlorophenylacetic acid ethyl ester
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 97% |
With toluene-4-sulfonic acid for 2h; Reflux; | 94% |
With hydrogenchloride Heating; | 90% |
2'-chloro-benzeneacetic acid
trimethyl orthoformate
methyl (2-chlorophenyl)acetate
Conditions | Yield |
---|---|
With sulfuric acid In methanol; water at 20℃; for 4h; | 97% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In acetonitrile at 60℃; for 5h; | 96% |
Conditions | Yield |
---|---|
Stage #1: 2'-chloro-benzeneacetic acid With copper(l) chloride; sodium hydroxide In water at 250℃; for 8h; Autoclave; Stage #2: methanol With sulfuric acid In dichloromethane Temperature; Reflux; | 95% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation; | 94% |
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.25h; Microwave irradiation; | 92% |
With 1H-imidazole; sodium periodate; {Mn(III)[5,10,15,20-tetrakis(4-H2N-Ph)porphyrin]}polystyrene In acetonitrile at 20℃; for 4h; | 90% |
2'-chloro-benzeneacetic acid
5-{1-[(2-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; | 94% |
2'-chloro-benzeneacetic acid
3-methoxy-4-(4-methyloxazol-5-yl)aniline
2-(2-chlorophenyl)-N-(3-methoxy4-(4-methyloxazol-5-yl)phenyl)acetamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 3.5h; | 94% |
2'-chloro-benzeneacetic acid
4-bromo-2-[2-(morpholin-4-yl)ethoxy]aniline
N-(4-bromo-2-(2-morpholinoethoxy)phenyl)-2-(2-chlorophenyl)acetamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 94% |
2'-chloro-benzeneacetic acid
2-Chlorobenzyl alcohol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; caesium carbonate In dichloromethane at 40℃; for 40h; Irradiation; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride In water | 93% |
2'-chloro-benzeneacetic acid
N,0-dimethylhydroxylamine
2-(2-chlorophenyl)-N-methoxy-N-methylacetamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; | 93% |
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 26h; Green chemistry; | 93% |
With iron(III) trifluoromethanesulfonate; sodium nitrite In dimethyl sulfoxide at 50℃; for 10h; Inert atmosphere; Sealed tube; | 46% |
2'-chloro-benzeneacetic acid
(2-aminophenyl)(phenyl)methanone
2-(2-chlorophenyl)-4-phenylquinazoline
Conditions | Yield |
---|---|
With ammonium acetate; oxygen; copper diacetate In 1-methyl-pyrrolidin-2-one at 120℃; under 760.051 Torr; for 20h; | 93% |
With ammonium acetate; oxygen; copper diacetate In 1-methyl-pyrrolidin-2-one at 120℃; under 760.051 Torr; for 20h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2'-chloro-benzeneacetic acid; isopropyl alcohol With sulfuric acid at 90℃; for 12h; Stage #2: With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h; | 92% |
Conditions | Yield |
---|---|
With iron(III) sulfate; bis[(2-pyridyl)methyl]amine In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; | 92% |
Conditions | Yield |
---|---|
With copper(II) oxide; sodium hydroxide In water at 200℃; under 750.075 Torr; for 12h; Autoclave; | 91.2% |
Molecular Structure of 2-Chlorophenylacetic acid (CAS NO.2444-36-2):
IUPAC Name: 2-(2-Chlorophenyl)acetic acid
Molecular Formula: C8H7ClO2
Molecular Weight: 170.59 g/mol
Density: 1.324 g/cm3
Melting Point: 92-95 °C(lit.)
Boiling Point: 294.1 °C at 760 mmHg
Flash Point: 131.7 °C
Index of Refraction: 1.569
Molar Refractivity: 42.26 cm3
Molar Volume: 128.8 cm3
Surface Tension: 49.3 dyne/cm
Enthalpy of Vaporization: 56.37 kJ/mol
Vapour Pressure: 0.000751 mmHg at 25 °C
XLogP3: 2
H-Bond Donor: 1
H-Bond Acceptor: 2
Index of Refraction: 1.569
Molar Refractivity: 42.26 cm3
Molar Volume: 128.8 cm3
Surface Tension: 49.3 dyne/cm
Canonical SMILES: C1=CC=C(C(=C1)CC(=O)O)Cl
InChI: InChI=1S/C8H7ClO2/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4H,5H2,(H,10,11)
InChIKey: IUJAAIZKRJJZGQ-UHFFFAOYSA-N
EINECS: 219-482-0
Product Categories: Phenylacetic acid series; Acids and Derivatives; Aromatic Phenylacetic Acids and Derivatives; Organic acids; C8; Carbonyl Compounds; Carboxylic Acids
2-Chlorophenylacetic acid (CAS NO.2444-36-2) is used as intermediate of diclofenac. It is also used in the synthesis of high efficient anti-inflammatory drugs. 2-Chlorophenylacetic acid can be used as pharmaceutical intermediates.
2-Chlorophenylacetic acid (CAS NO.2444-36-2) is obtained from o-chlorotoluene , o-chlorobenzyl chloride , and o-chlorophenyl acetonitrile .
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 13
Hazard Note: Irritant
2-Chlorophenylacetic acid (CAS NO.2444-36-2) is also named as (2-Chlorophenyl)acetic acid ; (o-Chlorophenyl)acetic acid ; Acetic acid, (o-chlorophenyl)- (8CI) ; Benzeneacetic acid, 2-chloro- (9CI) . It is white to light yellow powder.
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