6-Methoxy-1H-indole-3-carbonitrile

Base Information

• Chemical Name: 6-Methoxy-1H-indole-3-carbonitrile
• CAS No.: 145692-57-5
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.186
• DSSTox Substance ID: DTXSID60694848
• Wikidata: Q72490054
• Mol file: 145692-57-5.mol

Synonyms:6-METHOXY-1H-INDOLE-3-CARBONITRILE;145692-57-5;1H-Indole-3-carbonitrile, 6-methoxy-;3-CYANO-6-METHOXY-1H-INDOLE;SCHEMBL578915;DTXSID60694848;SLAJCUNVFURSMK-UHFFFAOYSA-N;MFCD07778405;1H-Indole-3-carbonitrile,6-methoxy-;AKOS006286610;AS-80324;CS-0147861;FT-0691095;A922338;A1-09425

Chemical Property of 6-Methoxy-1H-indole-3-carbonitrile

Chemical Property:

• Refractive Index: 1.64
• Boiling Point: 385 °C at 760 mmHg
• Flash Point: 186.6 °C
• PSA: 48.81000
• Density: 1.26 g/cm³
• LogP: 2.04818
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.063662883
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

98%min ^*data from raw suppliers

6-Methoxy-1H-indole-3-carbonitrile 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C(=CN2)C#N

Technology Process of 6-Methoxy-1H-indole-3-carbonitrile

There total 5 articles about 6-Methoxy-1H-indole-3-carbonitrile 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%

6-methoxy-1H-indole-3-carbaldehyde oxime (1261024-50-3) → 6-methoxyindole-3-carbonitrile (145692-57-5)

Guidance literature:

With pyridine; acetic anhydride; In tetrahydrofuran; for 9h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2013.05.026

Reference yield: 85.0%

6-methoxylindole (3189-13-7) + isocyanate de chlorosulfonyle (1189-71-5) → 6-methoxyindole-3-carbonitrile (145692-57-5)

Guidance literature:

In N,N-dimethyl-formamide; at 0 ℃; for 1h;

Reference yield: 77.0%

→ 6-methoxyindole-3-carbonitrile (145692-57-5)

Guidance literature:

upstream raw materials:

6-methoxy-1H-indole-3-carbaldehyde

6-methoxylindole

isocyanate de chlorosulfonyle

6-methoxy-1H-indole-3-carbaldehyde oxime

Downstream raw materials:

(S)-6-(3-cyano-1-cyclobutyl-6-(difluoromethoxy)-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide

C₂₆H₃₈F₂N₂OSn

C₁₉H₁₈FN₃O

C₁₉H₁₇N₃O₂

Refernces

• 1、 Zhang, Nanjing,Zhang, Xiaoyan,Zhu, Jin,Turpoff, Anthony,Chen, Guangming,Morrill, Christie,Huang, Song,Lennox, William,Kakarla, Ramesh,Liu, Ronggang,Li, Chunshi,Ren, Hongyu,Almstead, Neil,Venkatraman, Srikanth,Njoroge, F. George,Gu, Zhengxian,Clausen, Valerie,Graci, Jason,Jung, Stephen P.,Zheng, Yingcong,Colacino, Joseph M.,Lahser, Fred,Sheedy, Josephine,Mollin, Anna,Weetall, Marla,Nomeir, Amin,Karp, Gary M.. "Structure-activity relationship (SAR) optimization of 6-(Indol-2-yl) pyridine-3-sulfonamides: Identification of potent, selective, and orally bioavailable small molecules targeting hepatitis C (HCV) NS4B". . p. 2121 - 2135. Retrieved 2014/04/03.
• 2、 Kumar, Dalip,Kumar, N. Maruthi,Chang, Kuei-Hua,Gupta, Ritika,Shah, Kavita. "Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4- thiadiazoles". scheme or table. p. 5897 - 5900. Retrieved 2011/10/18.