Product Name

  • Name

    Meclofenamic acid

  • EINECS 211-419-5
  • CAS No. 644-62-2
  • Article Data17
  • CAS DataBase
  • Density 1.3567 (rough estimate)
  • Solubility
  • 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
  • Appearance
  • Safety Poison by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl− and NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 644-62-2 (Meclofenamic acid)
  • Hazard Symbols
  • 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);
  • PSA 49.33000
  • LogP 4.81660

Synthetic route

2,6-dichloro-3-methylaniline
64063-37-2

2,6-dichloro-3-methylaniline

Diphenyliodonium-2-carboxylate
1488-42-2

Diphenyliodonium-2-carboxylate

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With copper diacetate70%
With copper diacetate In isopropyl alcohol for 20h; Heating;0.9 g
2,6-dichloro-3-methylaniline
64063-37-2

2,6-dichloro-3-methylaniline

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With potassium carbonate; copper In N,N-dimethyl-formamide for 2h; Heating;18%
2,6-dichloro-3-methylaniline
64063-37-2

2,6-dichloro-3-methylaniline

potassium 2-bromobenzoate
16497-87-3

potassium 2-bromobenzoate

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With N-ethylmorpholine;; copper diacetate In N,N-dimethyl-formamide at 145℃; for 3h;
1,3-bis-(2,6-dichloro-3-methyl-phenyl)-1H-quinazoline-2,4-dione
13625-29-1

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

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol
2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid,methyl ester
3254-79-3

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

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With hydrazine hydrate In methanol
With hydrazine hydrate In methanol
2,6-dichloro-3-methylaniline
64063-37-2

2,6-dichloro-3-methylaniline

o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

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

meclofenamate sodium

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

Conditions
ConditionsYield
With hydrogenchloride In water
meclofenamic acid ethyl ester

meclofenamic acid ethyl ester

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

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

1-Adamantanamine

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

C10H17N*C14H11Cl2NO2

C10H17N*C14H11Cl2NO2

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

oxalyl dichloride

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid,methyl ester
3254-79-3

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

Conditions
ConditionsYield
In N-methyl-acetamide; methanol; dichloromethane94%
89%
thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C26H18Cl2NO2S2(1+)*C2F3O2(1-)

C26H18Cl2NO2S2(1+)*C2F3O2(1-)

Conditions
ConditionsYield
With Thianthrene In acetonitrile at -78 - 25℃;87%
...Expand
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

acetic acid
64-19-7

acetic acid

N-(2-(diethylamino)ethyl)-2-[(2,6-dichloro-3-methylphenyl)amino]benzamide acetate

N-(2-(diethylamino)ethyl)-2-[(2,6-dichloro-3-methylphenyl)amino]benzamide acetate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID; N,N-diethylethylenediamine With dicyclohexyl-carbodiimide In chloroform at 20℃; for 3h;
Stage #2: acetic acid In chloroform		85.8%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

2-(2,6-dichloro-3-methylphenylamino)benzohydrazide

2-(2,6-dichloro-3-methylphenylamino)benzohydrazide

Conditions
ConditionsYield
With hydrazine hydrate at 250℃; under 12929 Torr; for 0.0833333h; Microwave irradiation; Neat (no solvent);85%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

methyl 2-aminobutanoate hydrochloride
7682-18-0

methyl 2-aminobutanoate hydrochloride

(RS)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]butanoate

(RS)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]butanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: methyl 2-aminobutanoate hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		77%
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: methyl 2-aminobutanoate hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		62%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

3,4-dichlorobenzyl amine
102-49-8

3,4-dichlorobenzyl amine

N-(3,4-dichlorobenzyl)-2-(2,6-dichloro-3-methylphenylamino)-benzamide

N-(3,4-dichlorobenzyl)-2-(2,6-dichloro-3-methylphenylamino)-benzamide

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: 3,4-dichlorobenzyl amine In dichloromethane at 20℃;		70%
(R)-2-Phenoxy-1-propylamine
6437-49-6

(R)-2-Phenoxy-1-propylamine

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

2-(2,6-dichloro-3-methyl-phenylamino)-N-(2-phenoxy-propyl)-benzamide

2-(2,6-dichloro-3-methyl-phenylamino)-N-(2-phenoxy-propyl)-benzamide

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: (R)-2-Phenoxy-1-propylamine In dichloromethane at 20℃;		70%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

cyclohexylamine
108-91-8

cyclohexylamine

N-cyclohexyl-2-(2,6-dichloro-3-methylphenylamino)-benzamide

N-cyclohexyl-2-(2,6-dichloro-3-methylphenylamino)-benzamide

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: cyclohexylamine In dichloromethane at 20℃;		68%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

methyl (L)-leucinate hydrochloride
7517-19-3

methyl (L)-leucinate hydrochloride

(S)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-4-methylpentanoate

(S)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-4-methylpentanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: methyl (L)-leucinate hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		67%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]acetate

ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]acetate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: glycine ethyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		67%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzyl)-2-(2,6-dichloro-3-methylphenylamino)-benzamide

N-(4-chlorobenzyl)-2-(2,6-dichloro-3-methylphenylamino)-benzamide

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: 4-chlorobenzylamine In dichloromethane at 20℃;		67%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

benzylamine
100-46-9

benzylamine

N-benzyl-2-(2,6-dichloro-3-methyl-phenylamino)-benzamide
1347886-86-5

N-benzyl-2-(2,6-dichloro-3-methyl-phenylamino)-benzamide

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: benzylamine In dichloromethane at 20℃;		65%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

L-alanine methyl ester hydrochloride
2491-20-5

L-alanine methyl ester hydrochloride

(S)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]propanoate

(S)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]propanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: L-alanine methyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		63%
lead(II) nitrate

lead(II) nitrate

MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

catena-poly[bis[μ2-2-((2,6-dichloro-3-methylphenyl)amino)benzoate-κ2O,O']lead(II)]

catena-poly[bis[μ2-2-((2,6-dichloro-3-methylphenyl)amino)benzoate-κ2O,O']lead(II)]

Conditions
ConditionsYield
In methanol; water for 1.5h;57%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

L-leucine ethyl ester hydrochloride
2743-40-0

L-leucine ethyl ester hydrochloride

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-4-methylpentanoate

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-4-methylpentanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: L-leucine ethyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		52%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

S-benzyl-cysteine ethyl ester hydrochloride

S-benzyl-cysteine ethyl ester hydrochloride

ethyl 3-(benzylthio)-2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]propanoate

ethyl 3-(benzylthio)-2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]propanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: S-benzyl-cysteine ethyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		51%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

L-Valine ethyl ester hydrochloride
17609-47-1

L-Valine ethyl ester hydrochloride

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-methylbutanoate

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-methylbutanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: L-Valine ethyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		45%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

(L)-phenylalanine ethyl ester hydrochloride
3182-93-2

(L)-phenylalanine ethyl ester hydrochloride

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-phenyl propanoate

(S)-ethyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-phenyl propanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: (L)-phenylalanine ethyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		42%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

dimethyl L-aspartate hydrochloride
32213-95-9

dimethyl L-aspartate hydrochloride

(S)-dimethyl-2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]succinate

(S)-dimethyl-2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]succinate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: dimethyl L-aspartate hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		39%
MECLOFENAMIC ACID
644-62-2

MECLOFENAMIC ACID

D-Valine methyl ester hydrochloride
7146-15-8

D-Valine methyl ester hydrochloride

(R)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-methylbutanoate

(R)-methyl 2-[2-(2,6-dichloro-3-methylphenylamino)benzamido]-3-methylbutanoate

Conditions
ConditionsYield
Stage #1: MECLOFENAMIC ACID With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: D-Valine methyl ester hydrochloride With triethylamine In dichloromethane at 0 - 20℃;		37%

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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