Methyl 5-methoxy-1H-indole-2-carboxylate

Base Information

• Chemical Name: Methyl 5-methoxy-1H-indole-2-carboxylate
• CAS No.: 67929-86-6
• Molecular Formula: C11H11N O3
• Molecular Weight: 205.213
• Hs Code.: 2933990090
• European Community (EC) Number: 267-811-1
• DSSTox Substance ID: DTXSID70987314
• Nikkaji Number: J317.233C
• Wikidata: Q72490092
• Mol file: 67929-86-6.mol

Synonyms:67929-86-6;Methyl 5-methoxy-1H-indole-2-carboxylate;Methyl 5-methoxyindole-2-carboxylate;5-methoxy-1H-indole-2-carboxylic acid methyl ester;1H-INDOLE-2-CARBOXYLIC ACID, 5-METHOXY-, METHYL ESTER;EINECS 267-811-1;5-METHOXYINDOLE-2-CARBOXYLIC ACID METHYL ESTER;Oprea1_041586;SCHEMBL1104006;DTXSID70987314;OXXJVMUTSUYQBR-UHFFFAOYSA-N;AMY39663;Methyl5-methoxyindole-2-carboxylate;MFCD01074509;methyl 5-methoxy-1H-indolecarboxylate;AKOS004119469;AB08027;CCG-247447;AS-47541;CS-0102186;F14206;M-3508;A835938;1H-Indole-2-carboxylicacid,5-methoxy-,methyl ester

Chemical Property of Methyl 5-methoxy-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.14E-05mmHg at 25°C
• Melting Point: 233-235℃
• Refractive Index: 1.612
• Boiling Point: 370.1 °C at 760 mmHg
• Flash Point: 177.6 °C
• PSA: 51.32000
• Density: 1.253 g/cm³
• LogP: 1.96310
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

98%min ^*data from raw suppliers

Methyl5-Methoxy-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC(=C2)C(=O)OC
• Uses: Methyl 5-Methoxy-1H-indole-2-carboxylate is used in preparation of Sulfenylindoles via Iodine/Manganese catalyzed Dehydrogenative oxidative coupling reaction of Indoles with Thiols in anisole.Also, used in preparation of Indolyl Thioether with Bunte salts.

Technology Process of Methyl 5-methoxy-1H-indole-2-carboxylate

There total 16 articles about Methyl 5-methoxy-1H-indole-2-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: 98.7%

methanol (67-56-1) + 5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → methyl 5-methoxyindole-2-carboxylate (67929-86-6)

Guidance literature:

With sulfuric acid; for 6h; Reflux;

Reference yield: 96.0%

methyl 2-azido-3-(3-methoxyphenyl)acrylate (651331-47-4) → methyl 5-methoxyindole-2-carboxylate (67929-86-6)

Guidance literature:

In toluene; at 200 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1016/j.bmcl.2013.01.066

Reference yield: 88.0%

C11H11N3O3 → methyl 5-methoxyindole-2-carboxylate (67929-86-6)

Guidance literature:

With 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride; In 1,2-dichloro-ethane; for 18h; Molecular sieve; Reflux; Inert atmosphere;

DOI:10.1039/c0cc01825b

upstream raw materials:

5-methoxy-1H-indole-2-carboxylic acid

methyl iodide

methanol

N-Acetamidoacrylic acid

Downstream raw materials:

(5-methoxy-1H-indol-2-yl)methanol

methyl 5-methoxy-3-(phenylthio)-1H-indole-2-carboxylate

5-methoxy-1H-indole-2-carboxylic acid

<(5-Methoxy-1-methyl)indol-2-yl>carbaldehyde

Refernces

• 1、 Tsotinis, Andrew,Vlachou, Margarita,Kiakos, Konstantinos,Hartley, John A.,Thurston, David E.. "Design and synthesis of two cytotoxic analogs of the novel pyrrolo[1′,2′:1,2][1,4]diazepin [7,6-b]indol-5(6h)-one nucleus". . p. 512 - 513. Retrieved 2003.
• 2、 Li, Weihe,Wang, Hao,Liu, Shengping,Feng, Hua,Benassi, Enrico,Qian, Bo. "Iodine/Manganese Catalyzed Sulfenylation of Indole via Dehydrogenative Oxidative Coupling in Anisole". supporting information. p. 2666 - 2671. Retrieved 2020/05/25.
• 3、 Almutairi, Maha S.,Hassan, Eman S.,Keeton, Adam B.,Piazza, Gary A.,Abdelhameed, Ali S.,Attia, Mohamed I.. "Antiproliferative activity and possible mechanism of action of certain 5-methoxyindole tethered C-5 functionalized isatins". . p. 3069 - 3078. Retrieved 2019/09/10.