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Meclofenamic acid

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Name

Meclofenamic acid

EINECS 211-419-5
CAS No. 644-62-2 Density 1.3567 (rough estimate)
PSA 49.33000 LogP 4.81660
Solubility N/A Melting Point 257-259°C
Formula C14H11Cl2NO2 Boiling Point 399.4°C at 760 mmHg
Molecular Weight 296.153 Flash Point 195.3°C
Transport Information N/A Appearance N/A
Safety Poison by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl and NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 644-62-2 (Meclofenamic acid) Hazard Symbols N/A
Synonyms

N-(2, 6-Dichloro-m-tolyl)anthranilic acid;benzoic acid, 2-[(2,6-dichloro-3-methylphenyl)amino]-;Meclofenamic acid (USAN);Benzoic acid,2-[(2,6-dichloro-3-methylphenyl)- amino]-;Acido meclofenamico [INN-Spanish];Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-;2-(2, 6-Dichloro-3-methylphenyl)aminobenzoic acid;1/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19;Benzoic acid, 2-[ (2,6-dichloro-3-methylphenyl)amino]-;Meclofenamate;N-(3-Methyl-2, 6-dichlorophenyl)anthranilic acid;CL 583;Meclomen (free acid);Acide meclofenamique [INN-French];CI-583;Meclofenamic acid [USAN:BAN:INN];N-(2,6-Dichloro-3-methylphenyl)anthranilic acid;N-(2,6-Dichloro-m-tolyl)anthranilic acid;Acidum meclofenamicum [INN-Latin];Anthranilic acid, N-(2,6-dichloro-m-tolyl)-;INF 4668;2-((2,6-Dichloro-3-methylphenyl)amino)benzoic acid;2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid;2-[(2,6-dichloro-3-methyl-phenyl)amino]benzoic acid;Meclophenamic acid;Anthranilic acid, N- (2,6-dichloro-m-tolyl)-;N-(3-Methyl-2,6-dichlorophenyl)anthranilic acid;Arquel;INF-4668;N-(2,6-DICHLORO-m-TOLYL)ANTHRANILIC ACID;2-((2,6-DICHLORO-3-METHYLPHENYL)AMINO)-BENZOIC ACID (9CI);

Article Data 17

Meclofenamic acid Synthetic route

64063-37-2

2,6-dichloro-3-methylaniline

1488-42-2

Diphenyliodonium-2-carboxylate

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With copper diacetate70%
With copper diacetate In isopropyl alcohol for 20h; Heating;0.9 g
64063-37-2

2,6-dichloro-3-methylaniline

118-91-2

ortho-chlorobenzoic acid

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With potassium carbonate; copper In N,N-dimethyl-formamide for 2h; Heating;18%
64063-37-2

2,6-dichloro-3-methylaniline

16497-87-3

potassium 2-bromobenzoate

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With N-ethylmorpholine;; copper diacetate In N,N-dimethyl-formamide at 145℃; for 3h;
13625-29-1

1,3-bis-(2,6-dichloro-3-methyl-phenyl)-1H-quinazoline-2,4-dione

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol
3254-79-3

2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid,methyl ester

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With hydrazine hydrate In methanol
With hydrazine hydrate In methanol
64063-37-2

2,6-dichloro-3-methylaniline

445-29-4

o-fluoro-benzoic acid

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With hydrogenchloride In monoethylene glycol diethyl ether
6385-02-0

meclofenamate sodium

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With hydrogenchloride In water

meclofenamic acid ethyl ester

644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; ethanol
768-94-5

1-Adamantanamine

644-62-2

MECLOFENAMIC ACID

C10H17N*C14H11Cl2NO2

Conditions
ConditionsYield
In methanol at 20℃;100%
79-37-8

oxalyl dichloride

644-62-2

MECLOFENAMIC ACID

3254-79-3

2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid,methyl ester

Conditions
ConditionsYield
In N-methyl-acetamide; methanol; dichloromethane94%
89%

Meclofenamic acid Specification

Meclofenamic acid(CAS NO.644-62-2) is a non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.  With the Chemical Formula of C14H11Cl2NO2, Meclofenamic acid is also called Meclofen; Meclorfenamic; Arquel; INF 4668; N-(2,6-Dichloro-m-tolyl)anthranilic Acid; N-(3-Methyl-2,6-dichlorophenyl)anthranilic Acid; NSC 95309. Meclofenamic acid is a nonsteroidal anti-inflammatory drug (NSAID) with effects similar to those of aspirin. It is prescribed for musculoskeletal pain from soft tissue injury, bone and joint problems, and laminitis.

Physical properties about Meclofenamic acid are: (1)ACD/LogP: 5.438; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.55; (4)ACD/LogD (pH 7.4): 2.37; (5)ACD/BCF (pH 5.5): 103.19; (6)ACD/BCF (pH 7.4): 6.90; (7)ACD/KOC (pH 5.5): 279.32; (8)ACD/KOC (pH 7.4): 18.68; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.663; (13)Molar Refractivity: 77.172 cm3; (14)Molar Volume: 208.18 cm3; (15)Polarizability: 30.594 10-24cm3; (16)Surface Tension: 57.0439987182617 dyne/cm; (17)Density: 1.423 g/cm3; (18)Flash Point: 195.346 °C; (19)Enthalpy of Vaporization: 68.559 kJ/mol; (20)Boiling Point: 399.393 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19);
(2)InChIKey=SBDNJUWAMKYJOX-UHFFFAOYSA-N;
(3)Smilesc1c(c(ccc1)Nc1c(c(ccc1Cl)C)Cl)C(=O)O;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 109mg/kg (109mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 148, Pg. 422, 1965.
rat LD50 oral 100mg/kg (100mg/kg)   Agents and Actions, A Swiss Journal of Pharmacology. Vol. 7, Pg. 481, 1977.

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