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53-86-1

Basic Information
CAS No.: 53-86-1
Name: Indometacin
Molecular Structure:
Molecular Structure of 53-86-1 (Indometacin)
Formula: C19H16ClNO4
Molecular Weight: 357.79
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;
EINECS: 200-186-5
Density: 1.327 g/cm3
Melting Point: 155-162 °C
Boiling Point: 499.363 °C at 760 mmHg
Flash Point: 255.806 °C
Solubility: ethanol: 50 mg/mL
Appearance: White crystalline powder
Hazard Symbols: VeryT+, IrritantXi
Risk Codes: 28-36/37/38
Safety: 28-36/37-45-26
Transport Information: UN 2811 6.1/PG 1
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating;A n/a
B 65%
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
ConditionsYield
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℃;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In water at 30℃; Kinetics; Further Variations:; pH-values; Temperatures;

C23H20ClN3O4

53-86-1

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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Chemistry

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

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.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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 NOx.
Hazard Codes of Indometacin (CAS NO.53-86-1): VeryT+,IrritantXi
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

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- .