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89796-99-6

Basic Information
CAS No.: 89796-99-6
Name: Aceclofenac
Molecular Structure:
Molecular Structure of 89796-99-6 (Aceclofenac)
Formula: C16H13Cl2NO4
Molecular Weight: 354.18
Synonyms: Aceclofenac [INN:BAN];Glycolic acid, (o-(2,6-dichloroanilino)phenyl)acetate (ester);Benzeneacetic acid, 2-((2,6-dichlorophenyl)amino)-, carboxymethyl ester;Aceclofenacum;Aceclofenaco;2-(o-(2,6-Dichloranilino)phenylacetoxy)essigsaeure;
EINECS: 641-844-5
Density: 1.455 g/cm3
Melting Point: 149-153 °C
Boiling Point: 486 °C at 760 mmHg
Flash Point: 247.7 °C
Solubility: 32mg/L(32 oC)
Appearance: White crystalline solid
Hazard Symbols: T,N
Risk Codes: 25-36-50/53
Safety: 26-45-60-61
Transport Information:
PSA: 75.63000
LogP: 3.98030
Synthetic route
139272-68-7

2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester

89796-99-6

aceclofenac

Conditions
ConditionsYield
With hydrogenchloride; acetic anhydride; acetic acid In water at 60℃; for 3h; Temperature;98.5%
With formic acid In acetone at 65℃; for 0.166667h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;96.3%
With aluminum (III) chloride; acetic anhydride; acetic acid at 60 - 65℃; for 2.5h; Reagent/catalyst; Temperature; Large scale;83%
With trifluoroacetic acid In dichloromethane at 20℃; for 7h;57%
With formic acid at 40℃;

tert-butyl-[2-(2,6-dichloroanilino) phenyl] acetoxy acetate

89796-99-6

aceclofenac

Conditions
ConditionsYield
With formic acid In toluene at 0 - 35℃; for 2h; Product distribution / selectivity;95%
With formic acid; trifluoroacetic acid In toluene at 25 - 40℃; for 2.5 - 5.5h; Product distribution / selectivity;
With formic acid In toluene at 0 - 50℃; for 2 - 4.5h; Product distribution / selectivity;
100499-89-6

aceclofenac benzyl ester

89796-99-6

aceclofenac

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
15307-79-6

diclofenac sodium

89796-99-6

aceclofenac

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide
2: H2 / Pd/C
View Scheme
Multi-step reaction with 2 steps
1: potassium iodide / acetonitrile / 0.25 h / 30 °C / Microwave irradiation
2: formic acid / acetone / 0.17 h / 65 °C / Microwave irradiation
View Scheme
Multi-step reaction with 2 steps
1: potassium iodide / ethanol / 3 h / 61 - 65 °C / Large scale
2: acetic acid; acetic anhydride; aluminum (III) chloride / 2.5 h / 60 - 65 °C / Large scale
View Scheme

C35H29Cl2NO10

89796-99-6

aceclofenac

Conditions
ConditionsYield
With simulated intestinalfluid In methanol at 37℃; pH=7.4; Reagent/catalyst; pH-value; Solvent;
66-71-7

1,10-Phenanthroline

zirconyl nitrate

89796-99-6

aceclofenac

C28H22Cl2N3O6Zr(1+)*NO3(1-)*9H2O

Conditions
ConditionsYield
With potassium hydroxide In acetone for 8h; Reflux;89.35%
89796-99-6

aceclofenac

A

C16H13Cl2NO5

B

C14H11Cl2NO3

C

15307-78-5

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester

Conditions
ConditionsYield
In methanol at 20℃; for 6h; UV-irradiation;A 7%
B 5%
C 88%
66-71-7

1,10-Phenanthroline

6046-93-1

copper(II) acetate monohydrate

89796-99-6

aceclofenac

C28H24Cl2CuN3O6(1+)*C2H3O2(1-)*6H2O

Conditions
ConditionsYield
With potassium hydroxide In acetone for 8h; Reflux;80.04%
66-71-7

1,10-Phenanthroline

6018-89-9

nickel(II) acetate tetrahydrate

89796-99-6

aceclofenac

C28H24Cl2N3NiO6(1+)*C2H3O2(1-)*3H2O

Conditions
ConditionsYield
With potassium hydroxide In acetone for 8h; Reflux;78.08%
66-71-7

1,10-Phenanthroline

lanthanide(III)chloride heptahydrate

89796-99-6

aceclofenac

C28H24Cl2LaN3O6(2+)*9H2O*2Cl(1-)

Conditions
ConditionsYield
With potassium hydroxide In acetone for 8h; Reflux;76.11%
103-90-2

4-acetaminophenol

89796-99-6

aceclofenac

1452834-52-4

C24H20Cl2N2O5

Conditions
ConditionsYield
With trichlorophosphate In pyridine at 5℃; for 4h;73%
66-71-7

1,10-Phenanthroline

5970-45-6

zinc(II) acetate dihydrate

89796-99-6

aceclofenac

C28H24Cl2N3O6Zn(1+)*C2H3O2(1-)*3H2O

Conditions
ConditionsYield
With potassium hydroxide In acetone for 8h; Reflux;72.53%
64-17-5

ethanol

89796-99-6

aceclofenac

2-(2-[(2',6'-dichlorophenyl)amino]phenyl)acetoxyacetate

Conditions
ConditionsYield
With sulfuric acid for 6h; Reflux;65%
67-56-1

methanol

89796-99-6

aceclofenac

139272-66-5

C17H15Cl2NO4

Conditions
ConditionsYield
With tert.-butylnitrite at 40℃; for 48h;63%
With sulfuric acid Reflux;
89796-99-6

aceclofenac

4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

1,2,3,4-di-O-isopropylidene-D-α-galactopyranose-6-yl 2-(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetoxy)acetic acid

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;62%
38780-40-4, 52691-24-4, 61848-70-2, 61848-66-6, 61848-62-2

{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)

89796-99-6

aceclofenac

C22H26Cl3N3O4Pt

Conditions
ConditionsYield
With sodium carbonate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;50%
103362-70-5

potassium ethyl methylmalonate

89796-99-6

aceclofenac

ethyl 4-(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetoxy)-2-methyl-3-oxobutanoate

Conditions
ConditionsYield
Stage #1: aceclofenac With 1,1'-carbonyldiimidazole Inert atmosphere;
Stage #2: potassium ethyl methylmalonate With magnesium chloride Inert atmosphere;
43%
1576-87-0

trans-2-pentenal

119072-55-8, 7188-38-7

tert-butylisonitrile

105838-14-0

tert-butyl N-tosyloxycarbamate

89796-99-6

aceclofenac

tert-butyl (2S,3R)-2-{2-(tert-butylamino)-1-[2-(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetoxy)acetoxy]-2-oxoethyl}-3-ethylaziridine-1-carboxylate

Conditions
ConditionsYield
Stage #1: trans-2-pentenal; tert-butyl N-tosyloxycarbamate With (S)-α,α-bis(4-hexylphenylthio)-2-pyrrolidinemethanol trimethylsilylether; sodium carbonate In ethanol; water at 20℃; for 0.666667h; Green chemistry;
Stage #2: tert-butylisonitrile; aceclofenac In ethanol; water at 20℃; for 24h; Passerini Condensation; Green chemistry; diastereoselective reaction;
33%
4665-58-1

2-nitroxyethylammonium nitrate

89796-99-6

aceclofenac

183195-09-7

(N-(2-(nitrooxy)ethyl)carbamoyl)methyl 2-(2-((2,6-dichlorophenyl)-amino)phenyl)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride13%
89796-99-6

aceclofenac

15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

Conditions
ConditionsYield
With sodium hydroxide for 3h; Heating;
89796-99-6

aceclofenac

4'-hydroxy aceclofenac

Conditions
ConditionsYield
With NADPH-generating system In acetonitrile at 37℃; for 3h; pH=7.4; aq. phosphate buffer;
89796-99-6

aceclofenac

β-cyclodextrine

aceclofenac-β-cyclodextrin (1:1) inclusion complex

Conditions
ConditionsYield
In methanol; water for 0.75h;
50-00-0

formaldehyd

3244-54-0

3,6-dinitro-9H-carbazole

89796-99-6

aceclofenac

1246212-64-5

C29H20Cl2N4O8

Conditions
ConditionsYield
In methanol Mannich reaction; Cooling with ice; Reflux;
3244-54-0

3,6-dinitro-9H-carbazole

100-52-7

benzaldehyde

89796-99-6

aceclofenac

1246212-56-5

C35H24Cl2N4O8

Conditions
ConditionsYield
In methanol Mannich reaction; Cooling with ice; Reflux;
3244-54-0

3,6-dinitro-9H-carbazole

89796-99-6

aceclofenac

75-07-0

acetaldehyde

1246212-52-1

C30H22Cl2N4O8

Conditions
ConditionsYield
In methanol Mannich reaction; Cooling with ice; Reflux;
3244-54-0

3,6-dinitro-9H-carbazole

89796-99-6

aceclofenac

100-10-7

4-dimethylamino-benzaldehyde

1246212-60-1

C37H29Cl2N5O8

Conditions
ConditionsYield
In methanol Mannich reaction; Cooling with ice; Reflux;
89796-99-6

aceclofenac

1227857-41-1

2-chloro-2-oxoethyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate

Conditions
ConditionsYield
With thionyl chloride In benzene
With thionyl chloride at 20℃; for 18h; Temperature;
With thionyl chloride In tetrahydrofuran for 1.5h; Microwave irradiation;
89796-99-6

aceclofenac

1262333-96-9

2-[(2,6-dichlorophenyl)amino]-N1-(phenyl)-N4-phenylacetoxyacetamidobenzenesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / benzene
2: N,N-dimethyl-formamide / 24 h / 10 - 130 °C
View Scheme
Downstream Products
139272-66-5
15307-86-5
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    Specification: 1.Chemical name:[O - (2,6 - dichloro-aniline) - phenyl] acetoacetate 2.CAS: 89796-99-6 3.Molecular Formula:C16H13Cl2NO4 4.Molecular Weight:354.18 5.Purity: 99% 6.Appearance: White or white crystalline powd

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    English name: Aceclofenac Specification: BP2011/EP7.0 98% CAS NO.:89796-99-6 Appearance: White crystalline powder Molecular weight:354.18 Molecular formula:C16H13Cl2NO4 Appearance:White powder Storage:Store in cool and dry place, a

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Specification

The Aceclofenac, with the CAS registry number 89796-99-6,is also known as 2-[2-[2-(2,6-Dichlorophenyl)aminophenyl]acetyl]oxyacetic acid. It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Lipid signaling;Aromatics. Its EINECS number is 202-852-0. This chemical's molecular formula is C16H13Cl2NO4 and molecular weight is 354.19. What's more,Its systematic name is Aceclofenac.It is a White Crystalline Solid which is  a non-steroidal anti-inflammatory drug and it is manufactured by Intas Biopharmaceuticals.. Aceclofenac can be used for the relief of pain and inflammation in rheumatoid arthritis, osteoarthritis and ankylosing spondylitis.

Physical properties about Aceclofenac are:
(1)ACD/LogP:  3.807; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  0.96; (4)ACD/LogD (pH 7.4):  0.09; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  4.00; (8)ACD/KOC (pH 7.4):  1.00; (9)#H bond acceptors:  5; (10)#H bond donors:  2; (11)#Freely Rotating Bonds:  7; (12)Index of Refraction:  1.639; (13)Molar Refractivity:  87.572 cm3; (14)Molar Volume:  243.314 cm3; (15)Polarizability:  34.716 10-24cm3 ; (16)Surface Tension:  59.2470016479492 dyne/cm; (17)Density:  1.456 g/cm3; (18)Flash Point:  247.75 °C; (19)Enthalpy of Vaporization:  79.171 kJ/mol; (20)Boiling Point:  486.043 °C at 760 mmHg; (21)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Clc2cccc(Cl)c2Nc1ccccc1CC(=O)OCC(=O)O;
(2)Std. InChI:InChI=1S/C16H13Cl2NO4/c17-11-5-3-6-12(18)16(11)19-13-7-2-1-4-10(13)8-15(22)23-9-14(20)21/h1-7,19H,8-9H2,(H,20,21);
(3)Std. InChIKey:MNIPYSSQXLZQLJ-UHFFFAOYSA-N.

The toxicity data of Aceclofenac are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 130mg/kg (130mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 41, Pg. 1265, 1991.
women TDLo oral 20mg/kg/5D-I (20mg/kg) VASCULAR: STRICTIRA; CJAMGES OM VESSE;S

LUNGS, THORAX, OR RESPIRATION: SPUTUM

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Annals of Pharmacotherpy. Vol. 29, Pg. 1168, 1995.