[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid diethylcarbamoylmethylcarbamoyloxymethyl ester
A
2-amino-N,N-diethylacetamide
B
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With human plasma In phosphate buffer at 37℃; pH=7.4; | A n/a B 100% |
[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid 1-diethylcarbamoyl-2-phenyl-ethylcarbamoyloxymethyl ester
A
[2-(2,6-dichloroanilino)phenyl]acetic acid
B
N-(phenylalanyl)-N,N-diethylamine
Conditions | Yield |
---|---|
With human plasma In phosphate buffer at 37℃; pH=7.4; | A 100% B n/a |
diclofenac sodium
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 20 - 45℃; for 3h; pH=1.4 - 1.6; Solvent; | 99% |
With hydrogenchloride In water Cooling with ice; | 90% |
With hydrogenchloride In water at 0 - 20℃; | 70% |
2,6-Dichlorophenol
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 60 - 100℃; for 8h; Temperature; Reagent/catalyst; | 95% |
N,N-dimethyl-o-(2,6-dichloroanilino)phenylacetamide
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water | 92.9% |
2-[(2,6-dichlorophenyl)-N-benzylamino]-phenylacetic acid
water
1,2-dichloro-benzene
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane; toluene | 91.2% |
2-<(2,6-dichlorophenyl)amino>-α-(methylthio)phenylacetic acid
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With nickel In ethanol Heating; | 85% |
1-(2,6-dichlorophenyl)indolin-2-one
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
In hydrogenchloride; toluene liquid HCl; | 84.4% |
Naprelan
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; | 82.2% |
ortho-bromophenylacetic acid
2,6-Dichloroaniline
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With D-myo-inositol; copper; caesium carbonate In water at 100℃; for 30h; | 82% |
2'-chloro-benzeneacetic acid
2,6-Dichloroaniline
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; potassium iodide In 1,4-dioxane at 130 - 150℃; for 7h; Concentration; Solvent; Inert atmosphere; | 80% |
With copper(l) iodide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 165℃; for 12h; Ullmann Condensation; Sealed tube; | 34% |
With copper(I) chloride; potassium carbonate; potassium iodide In N,N-dimethyl-formamide; xylene at 150 - 152℃; for 5h; |
o-(N-allyl-2,6-dichloroanilino)phenylacetic acid
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; water; benzene | 72% |
ortho-bromophenylacetic acid
2,6-Dichloroaniline
diethylene glycol
A
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate; potassium carbonate at 110℃; for 12h; Inert atmosphere; | A 72% B 17% |
2-(2-iodophenyl)acetonitrile
2,6-Dichloroaniline
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Stage #1: 2-(2-iodophenyl)acetonitrile With potassium hydroxide In ethanol at 80℃; for 12h; Inert atmosphere; Sealed tube; Stage #2: 2,6-Dichloroaniline With copper(l) iodide; potassium carbonate In toluene at 100℃; for 12h; Inert atmosphere; Sealed tube; | 70% |
potassium 2-iodophenylacetate
2,6-Dichloroaniline
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; potassium carbonate at 100℃; Ullmann coupling; | 61% |
2-<(2,6-Dichlorphenacyl)amino>phenylessigsaeure-2-oxopropylester
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With buffer pH 8.0 In 1,4-dioxane; acetonitrile at 57℃; half-life time of hydrolysis at different pH; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
at 37℃; Rate constant; t1/2, simulated gastric fluid, rate plasma, further reagents, temperatures; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
at 37℃; Rate constant; t1/2, simulated gastric fluid, rate plasma, further reagents; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
at 37℃; Rate constant; t1/2, simulated gastric fluid, rate plasma, further reagents; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With NADPH-generating system; rat liver homogenate at 37℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction; |
diclofenac sodium
A
2-oxoindole
B
2,6-Dichlorophenol
C
1-(2,6-dichlorophenyl)indolin-2-one
D
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
In phosphate buffer at 45℃; Kinetics; Thermodynamic data; Further Variations:; pH-values; Temperatures; |
aceclofenac
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 3h; Heating; |
N-phenyl-2,6-dichloroaniline
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: benzene / 6 h / Heating 2: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 3: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 4: 91 percent / 2N NaOH / ethanol / 48 h / Heating 5: 85 percent / Raney nickel / ethanol / Heating View Scheme | |
Multi-step reaction with 5 steps 1: benzene / 6 h / Heating 2: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature 3: SnCl4 / CCl4 / 0.83 h / Ambient temperature 4: 91 percent / 2N NaOH / ethanol / 48 h / Heating 5: 85 percent / Raney nickel / ethanol / Heating View Scheme |
N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 2: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 3: 91 percent / 2N NaOH / ethanol / 48 h / Heating 4: 85 percent / Raney nickel / ethanol / Heating View Scheme | |
Multi-step reaction with 4 steps 1: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature 2: SnCl4 / CCl4 / 0.83 h / Ambient temperature 3: 91 percent / 2N NaOH / ethanol / 48 h / Heating 4: 85 percent / Raney nickel / ethanol / Heating View Scheme |
1-(2,6-dichlorophenyl)-3-(methylthio)oxindole
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / 2N NaOH / ethanol / 48 h / Heating 2: 85 percent / Raney nickel / ethanol / Heating View Scheme |
N-(2,6-dichlorophenyl)-α-(methylsulfinyl)acetanilide
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 2: 91 percent / 2N NaOH / ethanol / 48 h / Heating 3: 85 percent / Raney nickel / ethanol / Heating View Scheme |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: SnCl4 / CCl4 / 0.83 h / Ambient temperature 2: 91 percent / 2N NaOH / ethanol / 48 h / Heating 3: 85 percent / Raney nickel / ethanol / Heating View Scheme |
4-((3,3-dimethylbutoxy)carbonyloxy)benzyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With water at 37℃; pH=7.4; Kinetics; |
bromoacetic acid tert-butyl ester
[2-(2,6-dichloroanilino)phenyl]acetic acid
2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 20℃; | 100% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
(+)-O-Demethyltramadol
Conditions | Yield |
---|---|
With water In acetonitrile at 20℃; under 760.051 Torr; Product distribution / selectivity; | 100% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
(±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Product distribution / selectivity; | 100% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
O-desmethyltramadol
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Product distribution / selectivity; | 100% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
1-Adamantanamine
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Acylation; | 98% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
(2E)-3-phenyl-2-propen-1-ol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide at 20℃; for 4h; | 98% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
diazomethyl-trimethyl-silane
2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester
Conditions | Yield |
---|---|
In methanol; hexane; benzene at 25℃; for 1h; | 96% |
With methanol In Dimethyl ether |
methanol
[2-(2,6-dichloroanilino)phenyl]acetic acid
2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 0.25h; Reflux; | 96% |
Stage #1: methanol; [2-(2,6-dichloroanilino)phenyl]acetic acid With hydrogenchloride In water for 6h; Reflux; Stage #2: With sodium carbonate In water | 91% |
Stage #1: methanol; [2-(2,6-dichloroanilino)phenyl]acetic acid With hydrogenchloride In water for 6h; Reflux; Stage #2: With sodium hydrogencarbonate In water Cooling with ice; Saturated solution; | 91% |
1-hydroxy-pyrrolidine-2,5-dione
[2-(2,6-dichloroanilino)phenyl]acetic acid
acetic acid N-oxysuccinimide ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In 1,4-dioxane for 8h; Ambient temperature; | 95% |
With dicyclohexyl-carbodiimide In dichloromethane for 1h; | 90% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 5℃; | |
Stage #1: 1-hydroxy-pyrrolidine-2,5-dione; [2-(2,6-dichloroanilino)phenyl]acetic acid In tetrahydrofuran at 0 - 5℃; for 0.166667h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere; | |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
chlorosulfuric acid chloromethyl ester
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 1h; | 95% |
With Bu4HSO4 In dichloromethane; water at 20℃; for 1h; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
(5-methyl-2-phenyl-1,3-dioxan-5-yl)methyl 4-hydroxybenzoate
(5-methyl-2-phenyl-1,3-dioxan-5-yl)methyl 4-(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetoxy)benzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 18h; | 95% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
[(2R)-2-aminopropyl]carbamic acid,1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1.5h; Cooling with ice; | 95% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
1-(2,6-dichlorophenyl)indolin-2-one
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; | 94% |
With thionyl chloride In dichloromethane; ethyl acetate at 50℃; for 2h; Concentration; Temperature; | 92% |
With hydrogenchloride In acetonitrile at 78.85℃; for 5h; Rate constant; Kinetics; Mechanism; energy data: ΔH(activ.), ΔS(activ.); ΔE(activ.)var. amount of acetonitrile, var. temp.; |
[2-(2,6-dichloroanilino)phenyl]acetic acid
3-{Methyl{[(nitrosothio)cyclohexyl]methyl}amino)propan-1-ol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Acylation; | 94% |
Conditions | Yield |
---|---|
In acetone at 50 - 55℃; for 2h; pH=8.5 - 10.0; | 93.7% |
2,2-dimethyl-1,3-dioxolane
[2-(2,6-dichloroanilino)phenyl]acetic acid
A
1-(2,6-dichlorophenyl)indolin-2-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol Cyclization; | A n/a B 93% |
1-pyrrolidineethanol
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
In acetone | 92% |
Magnolol
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 92% |
With dmap In dichloromethane at 25 - 30℃; | 92% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere; Molecular sieve; | 92% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
2-ethyl-2-(nitrosothio)butan-1-ol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Acylation; | 91% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
ethanolamine
Conditions | Yield |
---|---|
In acetone | 90% |
[2-(2,6-dichloroanilino)phenyl]acetic acid
2-(2-tert-butyloxycarbonylaminoethoxy)ethanol
[2-(2,6-dichlorophenylamino)phenyl]acetic acid 2-(2-tert-butoxycarbonylaminoethoxy)ethyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; | 90% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h; Cooling with ice; | 1.166 g |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 35℃; for 2h; | 2.44 g |
The IUPAC name of Benzeneacetic acid,2-[(2,6-dichlorophenyl)amino]- is 2-[2-(2,6-dichloroanilino)phenyl]acetic acid. With the CAS registry number 15307-86-5, it is also named as Diclofenac. The product's categories are Indoles and Derivatives; Pharmacetical. It is a non-steroidal anti-inflammatory drug which originated from Ciba-Geigy (now Novartis) in 1973. And it was first introduced in the UK in 1979. Additioanlly, this drug may be supplied as either the sodium or potassium salt in the United Kingdom, India, Brazil and the United States. And most often as the sodium salt in China.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.206; (4)ACD/LogD (pH 7.4): 1.437; (5)ACD/BCF (pH 5.5): 76.63; (6)ACD/BCF (pH 7.4): 1.305; (7)ACD/KOC (pH 5.5): 322.878; (8)ACD/KOC (pH 7.4): 5.501; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.662; (13)Molar Refractivity: 76.531 cm3; (14)Molar Volume: 206.819 cm3; (15)Polarizability: 30.339×10-24 cm3; (16)Surface Tension: 57.998 dyne/cm; (17)Enthalpy of Vaporization: 70.067 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 295.016684; (21)MonoIsotopic Mass: 295.016684; (22)Topological Polar Surface Area: 49.3; (23)Heavy Atom Count: 19; (24)Complexity: 304.
Uses of Benzeneacetic acid,2-[(2,6-dichlorophenyl)amino]-: It is used to reduce inflammation and as an analgesic reducing pain in conditions such as arthritis or acute injury. It can also be used to reduce menstrual pain, dysmenorrhea. What's more, this drug is often used to treat chronic pain associated with cancer, particularly if inflammation is also present. It is used for musculoskeletal complaints. The Benzeneacetic acid,2-[(2,6-dichlorophenyl)amino]- is better tolerated NSAIDs. Though 20% of patients on long-term treatment experience side effects, only 2% have to discontinue the drug.
People can use the following data to convert to the molecule structure.
1. SMILES:c1ccc(c(c1)CC(=O)O)Nc2c(cccc2Cl)Cl
2. InChI:InChI=1/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | intramuscular | 1070ug/kg (1.07mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Annals of Internal Medicine. Vol. 117, Pg. 1058, 1992. |
man | TDLo | oral | 29mg/kg (29mg/kg) | BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" | Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 173, 1995. |
mouse | LD50 | intraperitoneal | 345mg/kg (345mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 43, Pg. 44, 1993. | |
mouse | LD50 | oral | 170mg/kg (170mg/kg) | Pharmazie. Vol. 37, Pg. 148, 1982. | |
rat | LD50 | oral | 62500ug/kg (62.5mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980. |
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