Indometacin supplier | CasNO.53-86-1

Name
Indometacin
EINECS 200-186-5
CAS No. 53-86-1
Article Data106
CAS DataBase
Density 1.327 g/cm³
Solubility ethanol: 50 mg/mL
Melting Point 155-162 °C
Formula C₁₉H₁₆ClNO₄
Boiling Point 499.363 °C at 760 mmHg
Molecular Weight 357.793
Flash Point 255.806 °C
Transport Information UN 2811 6.1/PG 1
Appearance White crystalline powder
Safety 28-36/37-45-26
Risk Codes 28-36/37/38
Molecular Structure
Hazard Symbols T+, Xi
Synonyms Indole-3-aceticacid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl- (8CI);1-(4-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid;Amuno;Chrono-Indocid 75;Confortid;Dolovin;Elmetacin;Flam;Indo-Rectolmin;Indo-Tablinen;IndoRich;Indocid;Indocid(pharmaceutical);Indomecol;Indomee;Indomethine;Indomod;Indoptic;Indoptol;Infrocin;Innamit;Mezolin;Mikametan;Mobilan;NSC 77541;Tannex;Vonum;a-[1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl]aceticacid;
PSA 68.53000
LogP 3.92730

Synthetic route

: 16401-99-3
indomethacin ethyl ester

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water for 1h; Reflux;	99%
With lithium hydroxide monohydrate In water at 25℃; for 6h;	657 mg

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

: 122-01-0
4-chloro-benzoyl chloride

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

Conditions

Conditions	Yield
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Large scale; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h; Large scale;	97%
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h;	95%
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane 1.) THF; Multistep reaction;

: 122-01-0
4-chloro-benzoyl chloride

: 17536-38-8
ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

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

Conditions

Conditions	Yield
Stage #1: ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 25℃; for 10h; Inert atmosphere; Stage #3: With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 6h; Inert atmosphere;	92%

: 24438-49-1
<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde

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

Conditions

Conditions	Yield
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 30h; Schlenk technique;	91%
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Schlenk technique;	91%
With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h; Schlenk technique;	78%
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h;	28.4 mg

: 26001-79-6
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester

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

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.666667h;	84%
With palladium 10% on activated carbon; hydrogen In ethyl acetate
With 10% Pd/C; hydrogen In ethyl acetate

: 1601-18-9
indomethacin methyl ester

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

Conditions

Conditions	Yield
With pyridine; lithium iodide for 20h; Reflux;	84%
Stage #1: indomethacin methyl ester With pyridine; lithium iodide for 20h; Reflux; Stage #2: With hydrogenchloride; water at 0℃;	83%
With pyridine; lithium iodide for 20h; Reflux;	83%

: 75302-98-6
acemetacin tert-butyl ester

A: C20H18ClNO3

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

Conditions

Conditions	Yield
With pyridine; iodine; aluminium In acetonitrile at 80℃; for 18h; chemoselective reaction;	A 20% B 70%

: sodium 2-(4-chlorobenzoyl)-2-(4-methoxyphenyl)-1-hydrazosulfonate

: 123-76-2
levulinic acid

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

Conditions

Conditions	Yield
With formic acid In acetic acid for 6h; Heating;	66%

: 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%

: 591-12-8
5-methyl-2-furanone

: 16390-07-1
N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine

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

Conditions

Conditions	Yield
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating;	A n/a B 65%

...Expand

: 19501-58-7
4-methoxyphenylhydrazine hydrochloride

: 122-01-0
4-chloro-benzoyl chloride

: 123-76-2
levulinic acid

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

Conditions

Conditions	Yield
Stage #1: 4-methoxyphenylhydrazine hydrochloride With aldehyde resin; triethylamine In dichloromethane at 45℃; Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃; Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃;	63%
Stage #1: 4-methoxyphenylhydrazine hydrochloride With polystyrene aldehyde resin; triethylamine In 1,2-dichloro-ethane at 45℃; Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃; Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃;

...Expand

: 137138-23-9
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indolyl-3-essigsaeure-2-oxo-propylester

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

Conditions

Conditions	Yield
With buffer pH 8.0 In 1,4-dioxane; acetonitrile at 57℃; half-life time of hydrolysis at different pH;

: 78458-11-4
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-2'-hydroxy-diethyloxide

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

B: 111-46-6
diethylene glycol

Conditions

Conditions	Yield
With isotonic phosphate buffer at 32℃; chemical and enzymatic stability; other temperature and reagents, other pH; other olygoethylene derivatives as substrates;

: (1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-3-indolyl]acetate

A: 136918-14-4
phthalimide

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

Conditions

Conditions	Yield
With phosphate buffer pH 7.4 In 1,4-dioxane; water at 37℃; for 6h; Rate constant; var. of pH, also in rabbit plasma;

: 4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

A: 123-08-0
4-hydroxy-benzaldehyde

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

Conditions

Conditions	Yield
With water In 1,4-dioxane at 37℃; Rate constant; t1/2; also without alkali;

: [1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-formyl-phenyl ester

A: 90-02-8
salicylaldehyde

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

Conditions

Conditions	Yield
With water In 1,4-dioxane at 27℃; Kinetics; Thermodynamic data; other temp.; ΔH (excit.), ΔS (excit.); t1/2; also without alkali;

: 1026091-18-8
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester

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

Conditions

Conditions	Yield
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis;

: 1026676-65-2
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,3-dioxo-2,3-dihydro-indol-1-ylmethyl ester

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

Conditions

Conditions	Yield
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis;

: 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

: C23H20ClN3O4

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

Conditions

Conditions	Yield
With water In acetonitrile at 39℃; pH=7.1; Kinetics;

: 78667-03-5
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-diethylamino)ethylester

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

Conditions

Conditions	Yield
With pooled human serum at 37℃; Kinetics;

: [2-(1-pyrrolidino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

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

Conditions

Conditions	Yield
With pooled human serum at 37℃; Kinetics;

: [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-piperidin-1-yl-ethyl ester

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

Conditions

Conditions	Yield
With pooled human serum at 37℃; Kinetics;

: [2-(4-morpholino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

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

Conditions

Conditions	Yield
With pooled human serum at 37℃; Kinetics;

: 76812-37-8
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-dimethylamino)ethylester

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

Conditions

Conditions	Yield
With pooled human serum at 37℃; Kinetics;

: 5354-81-4
sodium 2-(4-methoxyphenyl)diazene-1-sulfonate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C 2: 88 percent / AcONa / acetic acid / 6 h 3: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme

: 104-94-9
4-methoxy-aniline

4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene: 4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aq. HCl; NaNO2 / 0.5 h / -5 - 0 °C 1.2: 38 g / aq. Na2SO3; NaOH / 0.5 h / 5 °C 2.1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C 3.1: 88 percent / AcONa / acetic acid / 6 h 4.1: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme

: 4-Methoxyphenylhydrazin-β-sulfonsaeure Natriumsalz

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / AcONa / acetic acid / 6 h 2: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme

: 873657-14-8
N-(4-chlorobenzoyl)-2-iodo-4-methoxyaniline

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 2: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 3: IBX / ethyl acetate / 2 h / 80 °C 4: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme

: 768-94-5
1-Adamantanamine

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

: C19H16ClNO4*C10H17N

Conditions

Conditions	Yield
In methanol at 20℃;	100%

: tert-butyl (2,2-difluoro-3-hydroxypropyl)carbamate

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

: C27H29ClF2N2O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	100%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

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

: 104425-42-5
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	99%
With dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 20℃;	92%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 8h; Ambient temperature;	91%

: 123-08-0
4-hydroxy-benzaldehyde

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

: 4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	28%
With pyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide 1.) r.t., 24 h, 2.) 4 deg C, 24 h; Yield given. Multistep reaction;

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

: 6264-33-1
Indomethacin amide

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 1h;	99%
With N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide para-toluenesulfonate; ammonia; benzotriazol-1-ol In 1,4-dioxane; DMF (N,N-dimethyl-formamide); ethyl acetate at 0 - 20℃;	95%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonium chloride; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; Substitution;	84%

: 821-09-0
n-Pent-4-enyl alcohol

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

: 1019777-27-5
pent-4-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 40h; Inert atmosphere;	87%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;	84%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;	30%

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

: 16130-32-8
(4-chlorophenyl)(3-(2-hydroxyethyl)-5-methoxy-2-methyl-1H-indol-1-yl)methanone

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 5℃; for 18h;	98%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 22h; Cooling with ice;	91%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	90%

: 2,2,2,-trichloroethoxycarbonyl azide

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

: 2,2,2-trichloroethyl-((1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl)methyl)carbamic acid ester

Conditions

Conditions	Yield
With dmap; copper diacetate In acetonitrile at 80℃; for 0.25h; Schlenk technique; Sealed tube;	98%
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Curtius Rearrangement; Inert atmosphere;	93%

: N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

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

: 3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	98%

: 64-17-5
ethanol

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

: 16401-99-3
indomethacin ethyl ester

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h;	97%
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: ethanol With triethylamine In dichloromethane for 0.5h;	93%
With toluene-4-sulfonic acid In toluene at 140℃; for 6h; Dean-Stark;	90%

: 33467-76-4
(E)-hept-2-en-1-ol

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

: [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hept-2-enyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;	97%

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

: 100-46-9
benzylamine

: 572875-44-6
N-benzyl-2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetamide

Conditions

Conditions	Yield
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;	97%
With (2-iodo-4',5-dimethoxy-[1,1'-biphenyl]-3-yl)boronic acid In dichloromethane at 24 - 25℃; for 6h; Molecular sieve;	94%
With (2-bromophenyl)boronic acid In dichloromethane at 25℃; for 48h; Molecular sieve;	93%
With bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere;	85%

: 2916-68-9
2-(Trimethylsilyl)ethanol

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

: 1224508-94-4
2-(trimethylsilyl)ethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere;	97%

: 258841-42-8
isopropyloxycarbonyloxymethyl iodide

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

: 1268602-80-7
[(1-methyl)ethoxycarbonyloxy]methyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -15℃; Inert atmosphere; Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at -15℃; Inert atmosphere;	96.6%

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

: 20357-37-3
1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride

Conditions

Conditions	Yield
With thionyl chloride In benzene at 65 - 70℃; for 1h;	96.5%
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 3.5h;	96%
With oxalyl dichloride In dichloromethane at 20℃; for 8h; Inert atmosphere;	96%

: 111-76-2
2-Butoxyethanol

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

: [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-butoxy-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;	96%

: 4442-79-9
cyclohexylethan-1-ol

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

: [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-cyclohexyl-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;	96%

: 624-95-3
3,3-dimethylbutanol

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

: 1224508-90-0
3,3-dimethylbutyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere;	96%

: 1-methylbutylzinc bromide

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

: 2-(5-methoxy-2-methyl-1-(4-(pentan-2-yl)benzoyl)-1H-indol-3-yl)acetic acid

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice; Stage #2: 1-methylbutylzinc bromide In tetrahydrofuran; toluene at 23℃; for 2h; Inert atmosphere;	96%

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

: 765-30-0
Cyclopropylamine

: 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-cyclopropylacetamide

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 2h; Stage #2: Cyclopropylamine In tetrahydrofuran at 20℃; for 2h;	96%

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

: 134-96-3
syringic aldehyde

: C28H24ClNO7

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Steglich Esterification; Inert atmosphere;	96%

: 2695-48-9
8-Bromo-1-octene

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

: oct-7-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	96%

: 107-59-5
tert-Butyl chloroacetate

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

: 75302-98-6
acemetacin tert-butyl ester

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In toluene at 75℃; for 45h; Large scale;	95.7%

: 53064-79-2
iodomethyl pivaloate

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

: 99199-42-5
pivaloyloxymethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -10 - 20℃; Inert atmosphere; Stage #2: iodomethyl pivaloate In N,N-dimethyl acetamide at -20 - -15℃;	95.5%

: 371-41-5
4-Fluorophenol

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

: [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 4-fluoro-phenyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;	95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;

: 60-12-8
2-phenylethanol

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

: 63170-54-7
phenethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;	95%
With C10H10Zr(2+)2CF3O3S(1-)C4H8O at 80℃; for 24h; Sealed tube;	70%

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

: 15992-10-6
2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

Conditions

Conditions	Yield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With chloroformic acid ethyl ester Stage #2: With ammonium hydroxide; sodium hydroxide	95%
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃; for 0.5h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 3h; Stage #3: With water; sodium hydroxide In tetrahydrofuran	88%
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -10 °C 1.2: 0.5 h 2.1: ammonium hydroxide / tetrahydrofuran / 3 h / 20 °C 3.1: sodium hydroxide / tetrahydrofuran View Scheme

: 343925-76-8
O-<3-Hydroxypropyl>hydroxylamine

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

: 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl}-N-(3-hydroxypropoxy)acetamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	95%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	95%

Indometacin Chemical Properties

Molecular Structure:

Molecular Formula: C₁₉H₁₆ClNO₄
Molecular Weight: 357.7876
IUPAC Name: 2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
CAS NO: 53-86-1
Classification Code: Analgesics ; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory; Anti-inflammatory agents, non-steroidal; Antirheumatic Agents; Cardiovascular Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Gout suppressants; Human Data; Mutation data; Peripheral Nervous System Agents; Reproductive Control Agents; Reproductive Effect; Sensory System Agents; Tocolytic agents; Tumor data
Melting point: 155-162 °C
Index of Refraction: 1.619
Molar Refractivity: 94.59 cm³
Molar Volume: 269.5 cm³
Surface Tension: 47.4 dyne/cm
Density: 1.32 g/cm³
Flash Point: 255.8 °C
Enthalpy of Vaporization: 80.85 kJ/mol
Boiling Point: 499.4 °C at 760 mmHg
Vapour Pressure: 8.61E-11 mmHg at 25 °C
EINECS of Indometacin (CAS NO.53-86-1): 200-186-5

Indometacin Uses

Indometacin (CAS NO.53-86-1) is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms.

Indometacin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	oral	320mg/kg (320mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
cat	LDLo	intravenous	20200ug/kg (20.2mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 726, 1983.
dog	LD50	intravenous	100mg/kg (100mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
dog	LD50	oral	160mg/kg (160mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
guinea pig	LD	skin	> 100mg/kg (100mg/kg)	BEHAVIORAL: EXCITEMENT	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 3185, 1986.
guinea pig	LD50	intraperitoneal	143mg/kg (143mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
guinea pig	LD50	intravenous	180mg/kg (180mg/kg)		Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
guinea pig	LD50	oral	100mg/kg (100mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
hamster	LD50	oral	81mg/kg (81mg/kg)		Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
human	TDLo	oral	113mg/kg/8W-I (113mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: OTHER CHANGES	Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 636, 1983.
infant	TDLo	intravenous	200ug/kg (0.2mg/kg)	BLOOD: HEMORRHAGE	Journal of Pediatrics. Vol. 107, Pg. 312, 1985.
infant	TDLo	oral	400ug/kg/2D-I (0.4mg/kg)	GASTROINTESTINAL: NECROTIC GHANGES	Journal of Pediatrics. Vol. 107, Pg. 484, 1985.
mammal (species unspecified)	LD50	oral	8mg/kg (8mg/kg)		Indian Journal of Medical Research. Vol. 81, Pg. 621, 1985.
man	LDLo	oral	15mg/kg/2W-I (15mg/kg)	BLOOD: APLASTIC ANEMIA	Israel Journal of Medical Sciences. Vol. 17, Pg. 433, 1981.
man	TDLo	multiple routes	3557mg/kg/5Y- (3557mg/kg)	SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE"	American Journal of Ophthalmology. Vol. 73, Pg. 846, 1972.
man	TDLo	oral	714ug/kg (0.714mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Allergy. Vol. 54, Pg. 90, 1999.
man	TDLo	oral	4286ug/kg/2D- (4.286mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Postgraduate Medical Journal. Vol. 72, Pg. 186, 1996.
man	TDLo	oral	22500ug/kg/3W (22.5mg/kg)	LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" LIVER: OTHER CHANGES	British Medical Journal. Vol. 3, Pg. 155, 1967.
man	TDLo	oral	22500ug/kg/3W (22.5mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE	Annals of Pharmacotherpy. Vol. 29, Pg. 883, 1994.
man	TDLo	rectal	2586mg/kg/3.5 (2586mg/kg)	SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE"	American Journal of Ophthalmology. Vol. 73, Pg. 846, 1972.
man	TDLo	unreported	499mg/kg/87W- (499mg/kg)	BEHAVIORAL: STIFFNESS KIDNEY, URETER, AND BLADDER: HEMATURIA	Arthritis and Rheumatism. Vol. 20, Pg. 917, 1977.
mouse	LD50	intramuscular	18200ug/kg (18.2mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
mouse	LD50	intraperitoneal	10mg/kg (10mg/kg)		Archivos de Farmacologia y Toxicologia. Vol. 8, Pg. 201, 1982.
mouse	LD50	intravenous	30mg/kg (30mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1198, 1969.
mouse	LD50	oral	11841ug/kg (11.841mg/kg)		German Offenlegungsschrift Patent Document. Vol. #3005827,
mouse	LD50	subcutaneous	18300ug/kg (18.3mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rabbit	LD50	oral	135mg/kg (135mg/kg)		Drugs in Japan Vol. 6, Pg. 90, 1982.
rat	LD	skin	> 250mg/kg (250mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 3185, 1986.
rat	LD50	intramuscular	26300ug/kg (26.3mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rat	LD50	intraperitoneal	13mg/kg (13mg/kg)		Toxicology and Applied Pharmacology. Vol. 38, Pg. 127, 1976.
rat	LD50	intravenous	21mg/kg (21mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 655, 1981.
rat	LD50	oral	2420ug/kg (2.42mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1526, 1975.
rat	LD50	rectal	31900ug/kg (31.9mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 2259, 1986.
rat	LD50	subcutaneous	12mg/kg (12mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
women	TDLo	oral	2098ug/kg/1D- (2.098mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED	Southern Medical Journal. Vol. 78, Pg. 1390, 1985.
women	TDLo	oral	10mg/kg (10mg/kg)	BEHAVIORAL: COMA	Japanese Journal of Toxicology. Vol. 12, Pg. 337, 1999.

Indometacin Consensus Reports

Reported in EPA TSCA Inventory.

Indometacin Safety Profile

A poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: aplastic anemia, changes in kidney tubules, decreased urine volume, diarrhea, fibrous hepatitis, hemorrhage, hypermotility, liver changes, necrotic stomach changes, retinal changes. Human teratogenic effects by ingestion and intravenous routes: developmental abnormalities of the respiratory system and urogenital system, homeostasis, other neonatal effects. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic Cl⁻ and NO_x.
Hazard Codes of Indometacin (CAS NO.53-86-1): Very T+, Irritant Xi
Risk Statements: 28-36/37/38
R28: Very toxic if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 28-36/37-45-26
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
F: 8-10
HazardClass: 6.1
PackingGroup: I

Indometacin Specification

Synonyms of Indometacin (CAS NO.53-86-1) are (1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-yl)acetic acid ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure [German] ; 1-(p-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid ; 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid ; 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico ; 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl- ; Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl- .

Product Name

Indometacin

Synthetic route

Indometacin Chemical Properties

Indometacin Uses

Indometacin Toxicity Data With Reference

Indometacin Consensus Reports

Indometacin Safety Profile

Indometacin Specification

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