Methyl 3-cyano-1H-indole-5-carboxylate

Base Information

• Chemical Name: Methyl 3-cyano-1H-indole-5-carboxylate
• CAS No.: 194490-33-0
• Molecular Formula: C11H8N2O2
• Molecular Weight: 200.19300
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10598983
• Wikidata: Q82494806
• Mol file: 194490-33-0.mol

Synonyms:Methyl 3-cyano-1H-indole-5-carboxylate;194490-33-0;SCHEMBL6599204;Methyl3-cyano-1H-indole-5-carboxylate;DTXSID10598983;PAFUKZMNTQWTPL-UHFFFAOYSA-N;methyl 3-cyanoindole-5-carboxylate;AKOS015919781;DA-17855;F87826;A880189

Chemical Property of Methyl 3-cyano-1H-indole-5-carboxylate

Chemical Property:

• PSA: 65.88000
• LogP: 1.82618
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 200.058577502
• Heavy Atom Count: 15
• Complexity: 307

Purity/Quality:

98%min ^*data from raw suppliers

1H-INDOLE-5-CARBOXYLICACID,3-CYANO-,METHYLESTER 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)NC=C2C#N

Technology Process of Methyl 3-cyano-1H-indole-5-carboxylate

There total 3 articles about Methyl 3-cyano-1H-indole-5-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: 86.0%

methyl 3‐formyl‐1H‐indole‐5‐carboxylate (197506-83-5) → methyl 3-cyano-1H-indole-5-carboxylate (194490-33-0)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid; for 6.5h; Reflux;

Reference yield: 50.0%

N?cyanosuccinimide (135205-66-2) + 5-methoxycarbonylindole (1011-65-0) → methyl 3-cyano-1H-indole-5-carboxylate (194490-33-0)

Guidance literature:

With gallium(III) trichloride; In acetonitrile; at 80 ℃; for 12h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.9b00416

Reference yield:

3-formylindole-5-carboxylic acid (148563-41-1) → methyl 3-cyano-1H-indole-5-carboxylate (194490-33-0)

Guidance literature:

With thionyl chloride; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

upstream raw materials:

3-formylindole-5-carboxylic acid

methyl 3‐formyl‐1H‐indole‐5‐carboxylate

N?cyanosuccinimide

5-methoxycarbonylindole

Refernces

• 1、 -. "BENZOPYRAZOLE COMPOUNDS AND ANALOGUES THEREOF". Page/Page column 263. . Retrieved 2017/12/27.