ChemicalBook--->CAS DataBase List--->644-62-2

644-62-2

644-62-2 Structure

644-62-2 Structure
IdentificationBack Directory
[Name]

Meclofenamic acid
[CAS]

644-62-2
[Synonyms]

Arquel
INF 4668
Meclofen
NSC 95309
Meclorfenamic
Meclofenamic acid
Meclophenamic acid
Meclofenamic acid Solution, 100ppm
N-(2,6-Dichloro-m-tolyl)anthranilic Acid
2-(2,6-dichloro-3-methylanilino)benzoic acid
2-(2,6-dichloro-3-methyl-anilino)benzoic acid
N-(3-Methyl-2,6-dichlorophenyl)anthranilic Acid
2-[(2,6-Dichloro-3-methylphenyl)amino]benzoic acid
[EINECS(EC#)]

211-419-5
[Molecular Formula]

C14H11Cl2NO2
[MDL Number]

MFCD00072053
[MOL File]

644-62-2.mol
[Molecular Weight]

296.15
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

257-259°C
[Boiling point ]

399.4±42.0 °C(Predicted)
[density ]

1.3567 (rough estimate)
[refractive index ]

1.6070 (estimate)
[storage temp. ]

Refrigerator
[solubility ]

Chloroform (Slightly), Methanol (Slightly, Heated)
[form ]

Solid
[pka]

pKa 4.0 (Uncertain)
[color ]

Off-White to Light Orange
[EPA Substance Registry System]

Benzoic acid, 2-[(2,6-dichloro-3-methylphenyl)amino]- (644-62-2)
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Uses]

Anti-inflammatory; antipyretic
[Definition]

ChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoe (painful periods), osteoarthritis and rheumatoid arthritis.
[Originator]

Meclomen,Warner Lambert,US,1980
[Manufacturing Process]

A mixture consisting of 22.7 g potassium o-bromobenzoate, 16.6 g 2,6- dichloro-3-methylaniline, 12 ml N-ethylmorpholine, 60 ml diethylene glycol dimethyl ether, and 1.0 g anhydrous cupric bromide is heated in a nitrogen atmosphere at 145°C to 155°C for 2 hours. The reaction mixture is diluted with 60 ml diethylene glycol dimethyl ether and acidified with 25 ml concentrated hydrochloric acid. The acidic mixture is diluted with 100 ml of water and the liquid phase decanted from the insoluble oil. The insoluble oil is stirred with methanol and the crystalline N-(2,6-dichloro-3-methylphenyl) anthranilic acid which separates is collected and washed with methanol. The product, after recrystallization from acetone-water mixture, melts at 248°C to 250°C.
[Brand name]

Meclomen (Parke-Davis).
[Therapeutic Function]

Antiinflammatory
[Clinical Use]

Meclofenamat is a nonsteroidal anti-inflammatory drug used for the treatment of mild to moderate pain, musculoskeletal, and joint disorders like rheumatoid arthritis and osteoarthritis as well as dysmenorrhoea. Meclofenamate inhibits COX-1 and COX-2 and modifies ion channels.
[Side effects]

Meclofenamic acid is available as its sodium salt hydrate. This drug is indicated for the relief of acute and chronic rheumatoid arthritis and osteoarthritis. Gastrointestinal distress, including diarrhea, nausea, vomiting, and abdominal pain, is the most commonly reported adverse effect.
[Synthesis]

Meclofenamic acid, N-(2,6-dichloro-m-tolyl)anthranylic acid (3.2.20), is synthesized analogous to flufenamic acid, by the reaction of potassium salt of 2-bromobenzoic acid with 2,6-dichloro-3-methylaniline in the presence of copper (II) bromide in a mixture of N-ethylmorpholine and diglyme [82,83].

Synthesis_644-62-2

[Toxics Screening Level]

The ITSL for meclofenamic acid has been changed from 0.04 μg/m3 to 0.1 μg/m3 based on an annual averaging time.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

2-Chlorobenzoic acid-->4-Chloro-3-nitrotoluene-->N-Ethylmorpholine-->2,6-Dichloro-3-methylaniline
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