5-Methoxyindole-3-acetonitrile

Base Information

• Chemical Name: 5-Methoxyindole-3-acetonitrile
• CAS No.: 2436-17-1
• Molecular Formula: C11H10N2O
• Molecular Weight: 186.213
• Hs Code.: 2933990090
• European Community (EC) Number: 800-083-0
• DSSTox Substance ID: DTXSID00393707
• Nikkaji Number: J1.650.104B
• Wikidata: Q72490039
• ChEMBL ID: CHEMBL2377609
• Mol file: 2436-17-1.mol

Synonyms:5-Methoxyindole-3-acetonitrile;2436-17-1;2-(5-methoxy-1H-indol-3-yl)acetonitrile;5-Methoxy-3-indolylacetonitrile;(5-methoxy-1H-indol-3-yl)acetonitrile;2-(5-methoxy-1~{H}-indol-3-yl)ethanenitrile;3-(Cyanomethyl)-5-methoxyindole;AMY786;SCHEMBL2724551;CHEMBL2377609;DTXSID00393707;ZBQCXEREMRGOCO-UHFFFAOYSA-N;BCP26955;(5-methoxy-3-indolyl)-acetonitrile;5-Methoxy-1H-indole-3-acetonitrile;MFCD02094163;STL220633;AKOS005258779;5-Methoxy-3-indolylacetonitrile, 95%;(5-methoxy-1H-indol-3-yl)-acetonitrile;AC-27790;AS-11095;A5023;CS-0199379;FT-0650677;EN300-197564;M-3480;Z410711518;UOK

Chemical Property of 5-Methoxyindole-3-acetonitrile

Chemical Property:

• Appearance/Colour: Brown powder
• Vapor Pressure: 7.09E-07mmHg at 25°C
• Melting Point: 65-69 °C(lit.)
• Refractive Index: 1.638
• Boiling Point: 408.3 °C at 760 mmHg
• PKA: 16.02±0.30(Predicted)
• Flash Point: 200.7 °C
• PSA: 48.81000
• Density: 1.224 g/cm³
• LogP: 2.24258
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.079312947
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

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

5-Methoxyindole-3-acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2CC#N
• Uses: 5-Methoxyindole-3-acetonitrile is a versatile reactant used in the preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment. It is also used in the synthesis of carboline analogs as potent MAPKAP-K2 inhibitors. Reactant for preparation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitorsReactant for preparation of carboline analogs as potent MAPKAP-K2 inhibitorsReactant for preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatmentReactant for preparation of debromoflustramine B and labeled Me(3a)-13C-physostigmineReactant for preparation of physostigmine and physovenineReactant for preparation of phenethyl substituted indole derivatives as melatoninergic agonists and antagonists

Technology Process of 5-Methoxyindole-3-acetonitrile

There total 10 articles about 5-Methoxyindole-3-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: 90.0%

diethyl-(5-methoxy-1H-indol-3-ylmethyl)-amine (190182-60-6) + methyl iodide (74-88-4) → 5-methoxyindole-3-acetonitrile (2436-17-1)

Guidance literature:

In tetrahydrofuran; water; MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar;

DOI:10.1111/j.2042-7158.1997.tb06789.x

Reference yield: 74.0%

potassium cyanide (151-50-8) + diethyl-(5-methoxy-1H-indol-3-ylmethyl)-amine (190182-60-6) → 5-methoxyindole-3-acetonitrile (2436-17-1)

Guidance literature:

diethyl-(5-methoxy-1H-indol-3-ylmethyl)-amine; With methyl iodide; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

potassium cyanide; In tetrahydrofuran; for 2h; Further stages.; Heating;

DOI:10.1016/j.bmcl.2007.05.101

Reference yield: 54.0%

5-methoxylindole (1006-94-6) + 2-aminoacetonitrile hydrochloride (6011-14-9) → 5-methoxyindole-3-acetonitrile (2436-17-1)

Guidance literature:

2-aminoacetonitrile hydrochloride; With sodium nitrite; In water; at 55 ℃;

5-methoxylindole; With meso-tetraphenylporphyrin iron(III) chloride; In dichloromethane; water; at 20 ℃; for 2.33h; Inert atmosphere;

DOI:10.1002/anie.201813631

upstream raw materials:

5-methoxylindole

methanol

5-methoxygramine

potassium cyanide

Downstream raw materials:

(1-methyl-5-methoxy-1H-indol-3-yl)acetonitrile

[5-methoxy-1-(2-phenethyl)-1H-indol-3-yl]acetonitrile

2-(5-methoxyindol-3-yl)ethylamine

(1-benzyl-5-methoxy-1H-indol-3-yl)acetonitrile

Refernces

• 1、 Egami, Hiromichi,Hotta, Ryo,Otsubo, Minami,Rouno, Taiki,Niwa, Tomoki,Yamashita, Kenji,Hamashima, Yoshitaka. "Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst". supporting information. p. 5656 - 5660. Retrieved 2020/07/14.
• 2、 Kwon, Tae Hoon,Yoon, Ik Hwan,Shin, Ji-Sun,Lee, Young Hun,Kwon, Bong Jin,Lee, Kyung-Tae,Lee, Yong Sup. "Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells". . p. 2571 - 2574. Retrieved 2013/07/04.