2-(5-bromo-1H-indol-3-yl)acetonitrile

Base Information

• Chemical Name: 2-(5-bromo-1H-indol-3-yl)acetonitrile
• CAS No.: 774-14-1
• Molecular Formula: C10H7BrN2
• Molecular Weight: 235.083
• Hs Code.: 2933990090
• European Community (EC) Number: 894-736-7
• ChEMBL ID: CHEMBL5184713
• DSSTox Substance ID: DTXSID10550046
• Wikidata: Q72457328
• Mol file: 774-14-1.mol

Synonyms:2-(5-bromo-1H-indol-3-yl)acetonitrile;774-14-1;5-Bromoindole-3-acetonitrile;CHEMBL5184713;MFCD09954795;2-(5-bromanyl-1~{H}-indol-3-yl)ethanenitrile;5-Bromo-3-indolylacetonitrile;SCHEMBL2005588;DTXSID10550046;QPEAZVAMEMXQHF-UHFFFAOYSA-N;BDBM50590133;(5-bromo-1h-indol-3-yl)acetonitrile;AKOS009437009;(5-bromo-1H-indol-3-yl)-acetonitrile;EN300-67196;F50662;Z410711512;KC0

Chemical Property of 2-(5-bromo-1H-indol-3-yl)acetonitrile

Chemical Property:

• PSA: 39.58000
• LogP: 2.99648
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 233.97926
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

98%Min ^*data from raw suppliers

2-(5-Bromo-1H-indol-3-yl)acetonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)CC#N

Technology Process of 2-(5-bromo-1H-indol-3-yl)acetonitrile

There total 12 articles about 2-(5-bromo-1H-indol-3-yl)acetonitrile 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: 81.0%

potassium cyanide + 5-bromo-1H-indole-3-carboxaldehyde (877-03-2) → (5-bromo-1H-indol-3-yl)-acetonitrile (774-14-1)

Guidance literature:

5-bromo-1H-indole-3-carboxaldehyde; With sodium tetrahydroborate; formamide; In methanol; for 0.5h;

potassium cyanide; In methanol; at 100 ℃; for 2.5h;

Reference yield: 78.0%

potassium cyanide + 5-bromo-1H-indole (10075-50-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (5-bromo-1H-indol-3-yl)-acetonitrile (774-14-1)

Guidance literature:

5-bromo-1H-indole; formaldehyd; With acetic acid; dimethyl amine; In water; at 0 - 20 ℃; for 4h;

With methyl iodide; In dichloromethane; toluene; at 20 ℃; for 36h; Inert atmosphere;

potassium cyanide; In water; for 1h; Reflux;

Reference yield: 76.0%

→ (5-bromo-1H-indol-3-yl)-acetonitrile (774-14-1)

Guidance literature:

With methanol; sodium tetrahydroborate; formamide; at 20 ℃; for 0.25h;

In methanol; at 54 ℃; for 16h;

upstream raw materials:

potassium cyanide

5-bromo-1H-indole

N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine

trimethylsilyl cyanide

Downstream raw materials:

methyl 2-(5-bromo-1H-indole-3-yl)acetate

(5-bromo-1H-indol-3-yl)-acetic acid

kenpaullone

tert-butyl 5-bromo-3-(cyanomethyl)-1H-indole-1-carboxylate

Refernces

• 1、 See, Cheng Shang,Kitagawa, Mayumi,Liao, Pei-Ju,Lee, Kyung Hee,Wong, Jasmine,Lee, Sang Hyun,Dymock, Brian W.. "Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)". . p. 344 - 367. Retrieved 2018/07/25.
• 2、 -. "4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS". Page/Page column 340. . Retrieved 2016/06/14.