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Cas Database

53-86-1

53-86-1

Identification

  • Product Name:Indometacin

  • CAS Number: 53-86-1

  • EINECS:200-186-5

  • Molecular Weight:357.793

  • Molecular Formula: C19H16ClNO4

  • HS Code:29339900

  • Mol File:53-86-1.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):VeryT+, IrritantXi

  • Hazard Codes:T+,Xi,T

  • Signal Word:Danger

  • Hazard Statement:H300 Fatal if swallowedH317 May cause an allergic skin reaction H360 May damage fertility or the unborn child

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. SYMPTOMS: May cause gastrointestinal discomfort and possibly ulcerations. May aggravate psychiatric disturbances, epilepsy, and parkinsonism. May cause drowsiness and headache. ACUTE/CHRONIC HAZARDS: Very toxic. Hazardous decomposition products. May aggravate central nervous system disorders. Suspected teratogen. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains; Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Indomethacin
  • Packaging:25g
  • Price:$ 363
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  • Manufacture/Brand:Usbiological
  • Product Description:Indomethacin
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  • Manufacture/Brand:Usbiological
  • Product Description:Indomethacin
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  • Product Description:Indomethacin ≥99%(HPLC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Indomethacin >98.0%(HPLC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Indomethacin >98.0%(HPLC)(T)
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 62 Articles be found

Investigation of the chiral recognition ability of human carboxylesterase 1 using indomethacin esters

Takahashi, Masato,Takani, Daisuke,Haba, Masami,Hosokawa, Masakiyo

, p. 73 - 80 (2020)

Human carboxylesterase 1 (hCES1) is an enzyme that plays an important role in hydrolysis of pharmaceuticals in the human liver. In this study, elucidation of the chiral recognition ability of hCES1 was attempted using indomethacin esters in which various chiral alcohols were introduced. Indomethacin was condensed with various chiral alcohols to synthesize indomethacin esters. The synthesized esters were hydrolyzed with a human liver microsome (HLM) solution and a human intestine microsome (HIM) solution. High hydrolytic rate and high stereoselectivity were confirmed in the hydrolysis reaction in the HLM solution but not in the HIM solution, and these indomethacin esters were thought to be hydrolyzed by hCES1. Next, these indomethacin esters were hydrolyzed in recombinant hCES1 solution and the hydrolysis rates of the esters were calculated. The stereoselectivity confirmed in HLM solution was also confirmed in the hCES1 solution. In the hydrolysis reaction of esters in which a phenyl group is bonded next to the ester, the Vmax value of the (R) form was 10 times larger than that of the (S) form.

A fluorescent ESIPT-based benzimidazole platform for the ratiometric two-photon imaging of ONOO-: In vitro and ex vivo

Bull, Steven D.,Gardiner, Jordan E.,James, Tony D.,Kim, Hwan Myung,Odyniec, Maria L.,Park, Sang-Jun,Sedgwick, Adam C.,Webb, Emily C.,Yoon, Juyoung

, p. 7329 - 7334 (2020)

In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO-activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 μM, 6.53 μM and 0.81 μM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications. This journal is

1-acyl-indoles. II. A new syntheses of 1-(p-chlorobenzoyl)-5-methyoxy-3-indolyacetic acid and its polymorphism.

Yamamoto

, p. 17 - 19 (1968)

-

Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids

Watanabe, Kenji,Terao, Nodoka,Niwa, Takashi,Hosoya, Takamitsu

, p. 11822 - 11834 (2021/07/31)

To enhance the practicality of photouncaging system using 3-acyl-2-methoxyindolizines, direct acylation of indolizines with carboxylic acids was developed using condensation reagents, generally used for peptide coupling. This method allowed for caging a broad range of carboxylic acids with indolizines. The method enabled a facile synthesis of water-soluble caged bioactive carboxylic acids having an intramolecular photosensitizer. The efficient release of carboxylic acids from the synthesized caged compounds upon red light irradiation was confirmed in neutral buffered solutions.

PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS

-

Paragraph 0026, (2021/04/17)

The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.

Synthesis method of indometacin and analogues thereof

-

Paragraph 0059-0060; 0062; 0068-0070, (2020/04/29)

The invention belongs to the technical field of indometacin synthesis, and discloses a synthesis method of indometacin and analogues thereof. The synthesis method of indometacin and analogues thereofcomprises the following steps: directly introducing alkyl, aromatic ring or heteroaromatic ring to the C2 position of indole through palladium catalyzed reaction; introducing a carboxylic acid fragment to the C3 position of the indole; and introducing an aroyl group to the N1 position of the indole. The method solves the problems that most of existing indometacin synthesis methods carry out modification by constructing an indole ring, simple structure change of indometacin molecules based on the synthesis strategy often needs de novo synthesis and synthesis steps for later modification and structure-activity relationship research of the indometacin molecules are tedious.

Process route upstream and downstream products

Process route

C<sub>23</sub>H<sub>23</sub>ClN<sub>2</sub>O<sub>6</sub>
934343-40-5

C23H23ClN2O6

methyl N-methylcarbamate
6642-30-4

methyl N-methylcarbamate

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

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

Conditions
Conditions Yield
With aq. buffer; In acetonitrile; at 39 ℃; pH=7.1; Kinetics;
<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde
24438-49-1

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

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
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 ℃; for 3h; under 760.051 Torr; 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
acemetacin tert-butyl ester
75302-98-6

acemetacin tert-butyl ester

C<sub>20</sub>H<sub>18</sub>ClNO<sub>3</sub>

C20H18ClNO3

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
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;
70%
20%
acemetacin tert-butyl ester
75302-98-6

acemetacin tert-butyl ester

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

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

acemetacin
53164-05-9

acemetacin

Conditions
Conditions Yield
With iodine; aluminium; In acetonitrile; at 20 ℃; for 6h; chemoselective reaction;
66%
30%
indomethacin methyl ester
1601-18-9

indomethacin methyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
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%
indomethacin methyl ester; With pyridine; lithium iodide; for 20h; Reflux;
With hydrogenchloride; water; at 0 ℃;
83%
With pyridine; lithium iodide; for 20h; Reflux;
83%
4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

levulinic acid
123-76-2

levulinic acid

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

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

Conditions
Conditions Yield
4-methoxyphenylhydrazine hydrochloride; With aldehyde resin; triethylamine; In dichloromethane; at 45 ℃;
4-chloro-benzoyl chloride; With pyridine; at 80 ℃;
levulinic acid; With trifluoroacetic acid; In 1,2-dichloro-ethane; at 70 ℃;
63%
4-methoxyphenylhydrazine hydrochloride; With polystyrene aldehyde resin; triethylamine; In 1,2-dichloro-ethane; at 45 ℃;
4-chloro-benzoyl chloride; With pyridine; at 80 ℃;
levulinic acid; With trifluoroacetic acid; In 1,2-dichloro-ethane; at 70 ℃;
indomethacin ethyl ester
16401-99-3

indomethacin ethyl ester

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

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

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
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;
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 4-[2-(diethoxy-phosphoryloxy)-ethyl]-phenyl ester
1428774-23-5

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

C<sub>12</sub>H<sub>19</sub>O<sub>5</sub>P

C12H19O5P

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

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

Conditions
Conditions Yield
With glucose-6-phosphate dehydrogenase; β-D-glucose 6-phosphate; NADP; magnesium chloride; In aq. phosphate buffer; at 37 ℃; for 4h; pH=7.4; Time; Reagent/catalyst; Enzymatic reaction;
5-Methoxy-2-methylindole-3-acetic acid
2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

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

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

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

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