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Diclofenac

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Name

Diclofenac

EINECS 239-348-5
CAS No. 15307-86-5 Density 1.431 g/cm3
PSA 49.33000 LogP 4.43710
Solubility 1.278mg/L(30 oC) Melting Point 156-158oC
Formula C14H11Cl2NO2 Boiling Point 412 ºC at 760 mmHg
Molecular Weight 296.153 Flash Point 203 ºC
Transport Information N/A Appearance White to yellowish crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 15307-86-5 (1-(2,6-Dichlorophenyl)-2-indolinone) Hazard Symbols N/A
Synonyms

Aceticacid, [o-(2,6-dichloroanilino)phenyl]- (8CI);Diclac;Diclofenac acid;Diclofenamic acid;Diclomelan;Dicloreuma;N-(2,6-Dichlorophenyl)-o-aminophenylacetic acid;Pennsaid;Voltaflan;[o-(2,6-Dichloroanilino)phenyl]acetic acid;

Article Data 50

Diclofenac Synthetic route

934548-15-9

[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid diethylcarbamoylmethylcarbamoyloxymethyl ester

A

34105-57-2

2-amino-N,N-diethylacetamide

B

15307-86-5

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

Conditions
ConditionsYield
With human plasma In phosphate buffer at 37℃; pH=7.4;A n/a
B 100%
934548-16-0

[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid 1-diethylcarbamoyl-2-phenyl-ethylcarbamoyloxymethyl ester

A

15307-86-5

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

B

40847-09-4

N-(phenylalanyl)-N,N-diethylamine

Conditions
ConditionsYield
With human plasma In phosphate buffer at 37℃; pH=7.4;A 100%
B n/a
15307-79-6

diclofenac sodium

15307-86-5

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

Conditions
ConditionsYield
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%
87-65-0

2,6-Dichlorophenol

methyl 2-(2-(2-bromopropionamido)phenyl)acetate

15307-86-5

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

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 60 - 100℃; for 8h; Temperature; Reagent/catalyst;95%
21789-06-0

N,N-dimethyl-o-(2,6-dichloroanilino)phenylacetamide

15307-86-5

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

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water92.9%
70690-44-7

2-[(2,6-dichlorophenyl)-N-benzylamino]-phenylacetic acid

95-50-1

1,2-dichloro-benzene

15307-86-5

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

Conditions
ConditionsYield
In tetrahydrofuran; hexane; toluene91.2%
83281-95-2

2-<(2,6-dichlorophenyl)amino>-α-(methylthio)phenylacetic acid

15307-86-5

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

Conditions
ConditionsYield
With nickel In ethanol Heating;85%
15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

15307-86-5

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

Conditions
ConditionsYield
In hydrogenchloride; toluene liquid HCl;84.4%
26159-34-2

Naprelan

15307-86-5

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

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃;82.2%
18698-97-0

ortho-bromophenylacetic acid

608-31-1

2,6-Dichloroaniline

15307-86-5

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

Conditions
ConditionsYield
With D-myo-inositol; copper; caesium carbonate In water at 100℃; for 30h;82%

Diclofenac Specification

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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