6-Benzyloxyindole-3-acetonitrile

Base Information

• Chemical Name: 6-Benzyloxyindole-3-acetonitrile
• CAS No.: 57765-24-9
• Molecular Formula: C17H14N2O
• Molecular Weight: 262.311
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10399013
• Wikidata: Q82201310
• ChEMBL ID: CHEMBL2377607
• Mol file: 57765-24-9.mol

Synonyms:6-Benzyloxyindole-3-acetonitrile;57765-24-9;2-(6-(benzyloxy)-1H-indol-3-yl)acetonitrile;2-(6-phenylmethoxy-1H-indol-3-yl)acetonitrile;2-(6-BENZYLOXYINDOLYL)ACETONITRILE;2-[6-(BENZYLOXY)-1H-INDOL-3-YL]ACETONITRILE;SCHEMBL273357;CHEMBL2377607;DTXSID10399013;HJHSSPILWGQJSG-UHFFFAOYSA-N;AKOS005259127;(6-benzyloxy-1H-indol-3-yl)-acetonitrile;FT-0662890;B-1802;EN300-749151;F9995-2631

Chemical Property of 6-Benzyloxyindole-3-acetonitrile

Chemical Property:

• Melting Point: 130-133°C
• Boiling Point: 502.3 °C at 760 mmHg
• PKA: 16.48±0.30(Predicted)
• Flash Point: 257.6 °C
• PSA: 48.81000
• Density: 1.232 g/cm³
• LogP: 3.81298
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 262.110613074
• Heavy Atom Count: 20
• Complexity: 355

Purity/Quality:

98%Min ^*data from raw suppliers

2-(6-Benzyloxyindolyl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)C(=CN3)CC#N
• Uses: A hydroxytryptamine

Technology Process of 6-Benzyloxyindole-3-acetonitrile

There total 7 articles about 6-Benzyloxyindole-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: 86.0%

(6-benzyloxy-1H-indol-3-ylmethyl)trimethylammonium iodide (629662-36-8) → (6-benzyloxy-indol-3-yl)-acetonitrile (57765-24-9)

Guidance literature:

In ethanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;

Reference yield:

6-benzyloxy-1H-indole (15903-94-3) → (6-benzyloxy-indol-3-yl)-acetonitrile (57765-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid

2: CH₃I / Erwaermen des erhaltenen Methojodids mit NaCN in H₂O

With acetic acid; methyl iodide;

DOI:10.1002/hlca.19550380619

Reference yield:

sodium cyanide (773837-37-9) + 6-benzyloxy-1H-indole-3-carboxaldehyde (92855-64-6) → (6-benzyloxy-indol-3-yl)-acetonitrile (57765-24-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; formamide;

DOI:10.1016/j.bmcl.2013.02.114

upstream raw materials:

3-(dimethylaminomethyl)-6-benzyloxyindole

6-benzyloxy-1H-indole

6-(benzyloxy)-1H-indole-2-carboxylic acid

(4-benzyloxy-2-nitro-phenyl)-pyruvic acid

Downstream raw materials:

6-hydroxytryptamine

C₁₈H₁₆N₂O

C₁₉H₁₆N₂O₂

C₁₉H₁₆N₂O₃

Refernces

• 1、 -. "Azepinoindole derivatives as pharmaceutical agents". . . Retrieved 2008/06/13.