5-Benzyloxyindole-3-acetonitrile

Base Information

• Chemical Name: 5-Benzyloxyindole-3-acetonitrile
• CAS No.: 2436-15-9
• Molecular Formula: C17H14 N2 O
• Molecular Weight: 262.311
• Hs Code.: 2933998090
• European Community (EC) Number: 863-795-0
• NSC Number: 73391
• DSSTox Substance ID: DTXSID40947223
• Nikkaji Number: J2.550.814I
• Wikidata: Q72442314
• ChEMBL ID: CHEMBL1288718
• Mol file: 2436-15-9.mol

Synonyms:2436-15-9;5-BENZYLOXYINDOLE-3-ACETONITRILE;2-(5-(benzyloxy)-1H-indol-3-yl)acetonitrile;5-BENZOLOXY-3-INDOLEACETONITRILE;[5-(benzyloxy)-1h-indol-3-yl]acetonitrile;(5-Benzyloxyindol-3-yl)acetonitrile;2-(5-phenylmethoxy-1H-indol-3-yl)acetonitrile;2-[5-(benzyloxy)-1H-indol-3-yl]acetonitrile;5-Benzyloxy-3-indoleacetonitrile;(5-Benzyloxy-1H-indol-3-yl)-acetonitrile;NSC73391;1H-Indole-3-acetonitrile, 5-(phenylmethoxy)-;Oprea1_143940;SCHEMBL273476;2-Oxohex-5-en-3-yl benzoate;CHEMBL1288718;DTXSID40947223;ADPRFNVFBYHCJQ-UHFFFAOYSA-N;AMY14551;MFCD00022730;NSC-73391;AKOS005259236;AC-27786;AS-31059;(5-Benzyloxyindol-3-yl)acetonitrile, 97%;FT-0620048;EN300-83124;B-1800;F2167-1307;Z1238595706

Chemical Property of 5-Benzyloxyindole-3-acetonitrile

Chemical Property:

• Appearance/Colour: off-white crystalline powder / Light yellow crystalline powder
• Vapor Pressure: 3.21E-10mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Boiling Point: 502.3 °C at 760 mmHg
• PKA: 15.95±0.30(Predicted)
• Flash Point: 257.6 °C
• Density: 1.232 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• 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:

99% ^*data from raw suppliers

(5-Benzyloxyindol-3-yl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)NC=C3CC#N
• Uses: Reactant for preparation of of β-carboline derivatives as antioxidants in the LDL oxidation model 1 Reactant for preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment 2 Reactant for preparation of tryptamine analogs as antihypertensive agents. Reactant for preparation of of β-carboline derivatives as antioxidants in the LDL oxidation modelReactant for preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatmentReactant for preparation of tryptamine analogs as antihypertensive agents

Technology Process of 5-Benzyloxyindole-3-acetonitrile

There total 9 articles about 5-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: 88.0%

5-benzyloxytryptamine (20776-45-8) → NSC 73391 (2436-15-9)

Guidance literature:

With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 110 ℃; for 15h; under 2250.23 Torr; Autoclave; Green chemistry;

DOI:10.1002/cssc.201402613

Reference yield: 82.7%

3-(diethylaminomethyl)-5-benzyloxyindol (190182-62-8) + methyl iodide (74-88-4) → NSC 73391 (2436-15-9)

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:

5-benzyloxy-1H-indole (1215-59-4) → NSC 73391 (2436-15-9)

Guidance literature:

With methyl magnesium iodide; diethyl ether; Erwaermen des Reaktionsgemisches mit Chloracetonitril;

upstream raw materials:

5-benzyloxy-1H-indole

5-benzyloxygramine

3-(diethylaminomethyl)-5-benzyloxyindol

methyl iodide

Downstream raw materials:

3-(2-aminoethyl)-1H-indol-5-ol

(5-benzyloxy-1-methyl-indol-3-yl)-acetonitrile

(Z)-2-(5-benzyloxy-1H-indol-3-yl)-3-pyridin-3-yl-acrylonitrile

N‐{2‐[5‐(benzyloxy)‐1H‐indol‐3‐yl]ethyl}acetamide

Refernces

• 1、 Jagadeesh, Rajenahally V.,Junge, Henrik,Beller, Matthias. ""Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles". . p. 92 - 96. Retrieved 2015/02/19.
• 2、 -. "Positive modulators of nicotinic receptor agonists". Page/Page column 10. . Retrieved 2008/06/13.