acemetacin supplier | CasNO.53164-05-9

Name
Acemetacin
EINECS 258-403-4
CAS No. 53164-05-9
Article Data14
CAS DataBase
Density 1.36 g/cm³
Solubility
Melting Point 151.5 °C
Formula C₂₁H₁₈ClNO₆
Boiling Point 565.5 °C at 760 mmHg
Molecular Weight 415.83
Flash Point 295.8 °C
Transport Information UN 2811
Appearance Light yellow solid
Safety 22-25-36/37/39-45
Risk Codes 26/27/28
Molecular Structure
Hazard Symbols T+
Synonyms 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-aceticacid carboxymethyl ester;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-aceticacid carboxymethyl ester;2-[2-[1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl]acetyloxy]aceticacid;Acemet;Acemethacin;Acemix;Emflex;K 708;Rantudil;Rheumibis;Rheutrop;Solart;TV 1322;TVX 1322;
PSA 94.83000
LogP 3.47050

Synthetic route

: 75302-98-6
acemetacin tert-butyl ester

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
With hydrogenchloride; acetic anhydride In acetic acid at 80℃; for 5h; Large scale;	99.45%
With trifluoroacetic acid In dichloromethane at 20℃; for 48h;	80%

: 1601-20-3
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid tert-butyl ester

: 64-19-7
acetic acid

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride at 60℃; for 5h; Reagent/catalyst; Temperature; Large scale;	98.8%

: 53164-04-8
<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy>essigsaeurebenzylester

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 80℃; for 24h; Temperature;	97.8%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 20h;	95%
With hydrogen; palladium on activated charcoal In ethyl acetate at 40℃; for 1h;	93%

: 75302-98-6
acemetacin tert-butyl ester

A: 53-86-1
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

B: 53164-05-9
acemetacin

Conditions

Conditions	Yield
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction;	A 30% B 66%

: 19501-58-7
4-methoxyphenylhydrazine hydrochloride

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 53164-08-2
(5-Methoxy-2-methylindol-3-acetoxy)essigsaeurebenzylester

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 53-86-1
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) K2CO3 / 1.) DMF, 45 min, 50 deg C, 2.) 3 h, 50 deg C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 123-76-2
levulinic acid

phosphorus pentasulfide: phosphorus pentasulfide

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) K2CO3 / 1.) DMF, 70 min, 40 deg C, 2.) 4 h, 50 deg C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 53164-03-7
Laevulinoyloxyessigsaeurebenzylester

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 4-Methoxyphenylhydrazin-β-sulfonsaeure Natriumsalz

: 53164-05-9
acemetacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 68 percent / conc. HCl / H2O / 2 h / 20 °C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme

: 145459-16-1
N-methyl-N-(2-nitrooxyethyl)ammonium nitrate

: 53164-05-9
acemetacin

: 646511-41-3
(N-methyl-N-(2-(nitrooxy)ethyl)carbamoyl)methyl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate

Conditions

Conditions	Yield
With 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; dmap; triethylamine In dichloromethane at 20℃;	85%

: 4665-58-1
2-nitroxyethylammonium nitrate

: 53164-05-9
acemetacin

: 646511-43-5
(N-(2-(nitrooxy)ethyl)carbamoyl)methyl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate

Conditions

Conditions	Yield
With 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 2-(Dimethylamino)pyridine	60%

: 38780-40-4, 52691-24-4, 61848-70-2, 61848-66-6, 61848-62-2
{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)

: 53164-05-9
acemetacin

: C27H31Cl2N3O6Pt

Conditions

Conditions	Yield
With sodium carbonate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;	53%

: 67-56-1
methanol

: 53164-05-9
acemetacin

: 2-methoxy-2-oxoethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With tert.-butylnitrite at 40℃; for 48h; Green chemistry;	48%

: 53164-05-9
acemetacin

: 91421-42-0
rubitecan

: acemetacin

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In DMF (N,N-dimethyl-formamide) at 20℃; for 96h;	32%

: 53164-05-9
acemetacin

A: 2-(4-Chlorphenyl)-6-methoxy-4H-3.1-benzoxazinon-4

B: N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester

C: <2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester

D: <2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure

Conditions

Conditions	Yield
With oxygen; methylene blue In methanol for 10h; Irradiation; Further byproducts given;	A 24% B 21% C 11% D 21%

...Expand

: 53164-05-9
acemetacin

A: 2-Acetyl-N-(4-chlor-benzoyl)-4-methoxy-anilin

B: N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester

C: <2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester

D: <2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure

Conditions

Conditions	Yield
With oxygen; methylene blue In methanol for 10h; Irradiation; Further byproducts given;	A 10% B 21% C 11% D 21%

...Expand

: 53164-05-9
acemetacin

A: 5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester

B: 74-11-3
para-chlorobenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide at 30℃; Kinetics; Equilibrium constant; Further Variations:; Solvents; detergents; micelles; zwitterionic micelles;
With borate buffer at 30℃; pH=9.65; Kinetics; Equilibrium constant; Further Variations:; with/without L-α-phosphatidylcholine vesicles; detergents; micelles;
With perchloric acid In water at 25℃; Kinetics; Product distribution;

: 53164-05-9
acemetacin

A: 2882-15-7
5-Methoxy-2-methylindole-3-acetic acid

B: 53-86-1
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

C: 5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester

D: 74-11-3
para-chlorobenzoic acid

Conditions

Conditions	Yield
In water at 30℃; Kinetics; Further Variations:; pH-values; Temperatures;

...Expand

: 53164-05-9
acemetacin

: 1613-88-3
4-chloro-N-hydroxybenzamide

Conditions

Conditions	Yield
Stage #1: acemetacin With sodium hydroxide; hydroxylamine hydrochloride Stage #2: With hydrogenchloride; iron(III) chloride

: Cu2(CH3COO)4(H2O)2

: 53164-05-9
acemetacin

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: bis(N,N-dimethylformamide)bis-(O,O'-ACM)copper(II)

B: bis(N,N-dimethylformamide)tetrakis-μ-(O,O'-ACM)dicopper(II)

Conditions

Conditions	Yield
at 20 - 35℃;

...Expand

: 288-32-4
1H-imidazole

: Cu2(CH3COO)4(H2O)2

: 53164-05-9
acemetacin

: bis(O,O'-acemetacin)bis(imidazole)copper(II)

Conditions

Conditions	Yield
In methanol; water for 0.416667h;

...Expand

: 557-34-6
zinc diacetate

: 7732-18-5
water

: 53164-05-9
acemetacin

: bis(O,O'-acemetacin)diaquzinc(II)

Conditions

Conditions	Yield
In ethanol at 60℃;

...Expand

: Cu2(CH3COO)4(H2O)2

: 7732-18-5
water

: 53164-05-9
acemetacin

: bis(O,O'-acemetacin)diaquacopper(II)

Conditions

Conditions	Yield
In ethanol at 20 - 40℃;

...Expand

: [Co(NH3)5(OSO2CF3)](CF3SO3)2

: 53164-05-9
acemetacin

: pentaammine(acemetacin)cobalt(III) bis(trifluoromethanesuIfonate)

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 50 - 80℃; for 5h;

: 98461-21-3
1,2,3,4-tetra-O-trimethylsilyl-β-D-glucopyranose

: 53164-05-9
acemetacin

: C39H60ClNO11Si4

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;

: 116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1
Duloxetine

: 53164-05-9
acemetacin

: 1309349-71-0
acemetacin (S)-duloxetine salt

Conditions

Conditions	Yield
Stage #1: Duloxetine; acemetacin In tetrahydrofuran; methanol Stage #2: In di-isopropyl ether at 12℃; for 12h;
In tetrahydrofuran; methanol Product distribution / selectivity;

acemetacin Chemical Properties

Systematic (IUPAC) name :2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic acid
Formula: C₂₁H₁₈ClNO₆
Mol. mass :415.82372 g/mol

acemetacin History

Acemetacin is manufactured by Merck under the tradename Emflex, and is available in the UK as a prescription-only drug.

acemetacin Uses

Acemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain.
Acemetacin, a glycolic acid ester of indometacin, acts as a prodrug; in the body, it is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects.

acemetacin Consensus Reports

An advantage of acemetacin is that it reduces gastric damage when compared to indometacin.

Product Name

Acemetacin

Synthetic route

acemetacin Chemical Properties

acemetacin History

acemetacin Uses

acemetacin Consensus Reports

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