Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate
• CAS No.: 7598-91-6
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Hs Code.: 29339980
• European Community (EC) Number: 231-507-7
• NSC Number: 405600
• UNII: NV7P3AB9BM
• DSSTox Substance ID: DTXSID40226883
• Nikkaji Number: J236.688F
• Wikidata: Q72475257
• ChEMBL ID: CHEMBL1366600
• Mol file: 7598-91-6.mol

Synonyms:7598-91-6;Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate;Ethyl 5-hydroxy-2-methylindole-3-carboxylate;1H-Indole-3-carboxylic acid, 5-hydroxy-2-methyl-, ethyl ester;2-Methyl-3-carbethoxy-5-hydroxyindole;NV7P3AB9BM;5-Hydroxy-2-methylindole-3-carboxylic acid ethyl ester;5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester;EINECS 231-507-7;MFCD00044575;NSC-405600;Mecarbin;NSC405600;Enamine_001244;UNII-NV7P3AB9BM;Oprea1_574903;cid_82073;MLS000052950;BIDD:GT0194;SCHEMBL2005093;CHEMBL1366600;BDBM32211;DTXSID40226883;HMS1397I12;HMS2375G22;AM1180;BBL012755;CCG-41544;STK747060;3-carbethoxy-5-hydroxy-2-methylindole;AKOS000275081;CS-W010473;HY-W009757;NSC 405600;SDCCGMLS-0034936.P002;SDCCGMLS-0034936.P003;s10748;AC-23422;BP-13118;NS-00007;SMR000068907;FT-0620465;EN300-31513;ethyl 5-hydroxy-2-methyl-indole-3-carboxylate;H-6800;3-ETHOXYCARBONYL-5-HYDROXY-2-METHYLINDOLE;SR-01000508033;3-(ETHOXYCARBONYL)-2-METHYL-5-HYDROXYINDOLE;ethyl 2-methyl-5-oxidanyl-1H-indole-3-carboxylate;Ethyl 5-hydroxy-2-methylindole-3-carboxylate, 97%;SR-01000508033-1;SR-01000508033-3;Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate #;Z56790866;F2137-0002;5-Hydroxy-2-methyl-1H-indole-3-carboxylicacid,ethylester;5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, ethyl ester;INDOLE-3-CARBOXYLIC ACID, 5-HYDROXY-2-METHYL-, ETHYL ESTER

Chemical Property of Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate

Chemical Property:

• Appearance/Colour: off-white to light tan crystalline powder
• Vapor Pressure: 3.4E-07mmHg at 25°C
• Melting Point: 205-208 °C(lit.)
• Refractive Index: 1.64
• Boiling Point: 406.7 °C at 760 mmHg
• Flash Point: 199.7 °C
• PSA: 62.32000
• Density: 1.282 g/cm³
• LogP: 2.35860
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl5-Hydroxy-2-methyl-1H-indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC2=C1C=C(C=C2)O)C
• Uses: Ethyl 5-Hydroxy-2-methyl-1H-indole-3-carboxylate is useful for preparation and study of hypoxia-selective cytotoxicity of indolequinone antitumor agents. Reactant for preparation of:Potential anti-inflammatory and analgesic agentsHistamine-3 receptor inverse agonists for the treatment of obesityTubulin Polymerization Inhibitors4,7-dioxoindole-3-methyl prodrugsAntagonists at M4 muscarinic receptors

Technology Process of Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate

There total 13 articles about Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

5-tert-butoxycarbonyloxy-2-methyl-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester → ethyl 5-hydroxy-2-methylindole-3-carboxylate (7598-91-6)

Guidance literature:

With sodium carbonate; In 1,2-dimethoxyethane; water; for 15h; Heating;

DOI:10.1016/j.tetlet.2006.09.129

Reference yield: 90.0%

ethyl 3-aminobut-2-enoate (626-34-6) + p-benzoquinone (106-51-4) → ethyl 5-hydroxy-2-methylindole-3-carboxylate (7598-91-6)

Guidance literature:

With acetic acid; at 15 - 40 ℃; for 2.5h;

DOI:10.1007/s11164-010-0210-x

Reference yield: 88.8%

C12H12BF3NO2(1-)*K(1+) → ethyl 5-hydroxy-2-methylindole-3-carboxylate (7598-91-6)

Guidance literature:

With dihydrogen peroxide; In ethanol; water; at 10 - 20 ℃; for 3h;

upstream raw materials:

ethyl aminocrotonate

p-benzoquinone

ethyl (E)-3-aminobut-2-enoate

ethyl 3-aminobut-2-enoate

Downstream raw materials:

2-methyl-4,5-dioxo-3-ethoxycarbonyl-4,5-dihydroindole

3-benzyl-2-methyl-1H-indole-5-ol

3-benzyl-4-dimethylaminomethyl-2-methyl-1H-indol-5-ol

mecarbinate

Refernces

• 1、 -. "MUSCARINIC ACETYLCHOLINE RECEPTOR SUBTYPE 4 ANTAGONISTS IN THE TREATMENT OF ANEMIA". Paragraph 00141-00142. . Retrieved 2020/10/20.
• 2、 Huang, Yun-Sheng,Zhang, Wen-Qing,Zhang, Xu,Wang, Jian-Zhong. "Manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole". experimental part. p. 975 - 983. Retrieved 2011/12/03.