2-(5-nitro-1H-indol-3-yl)ethanamine

Base Information

• Chemical Name: 2-(5-nitro-1H-indol-3-yl)ethanamine
• CAS No.: 55747-72-3
• Molecular Formula: C10H11N3O2
• Molecular Weight: 205.216
• European Community (EC) Number: 831-425-7
• DSSTox Substance ID: DTXSID20204301
• Nikkaji Number: J64.786A
• Wikidata: Q83077741
• Mol file: 55747-72-3.mol

Synonyms:55747-72-3;2-(5-nitro-1H-indol-3-yl)ethanamine;3-(2-AMINOETHYL)-5-NITROINDOLE;5-Nitrotryptamine;1H-Indole-3-ethanamine, 5-nitro-;2-(5-nitro-1H-indol-3-yl)ethan-1-amine;CBDivE_014657;5-Nitro-1H-indole-3-ethanamine;Oprea1_010029;Oprea1_339308;5-Nitrotryptamine, free base;SCHEMBL1520627;DTXSID20204301;GPZRBKWRRKBOAC-UHFFFAOYSA-N;BBL001125;MFCD00458822;STK366248;AKOS005443179;PD075990;VS-00814;FT-0600787;EN300-194545;N-8150;A830786;Z978942450

Chemical Property of 2-(5-nitro-1H-indol-3-yl)ethanamine

Chemical Property:

• Vapor Pressure: 9.61E-08mmHg at 25°C
• Refractive Index: 1.701
• Boiling Point: 434.3 °C at 760 mmHg
• PKA: 15.45±0.30(Predicted)
• Flash Point: 216.4 °C
• PSA: 87.63000
• Density: 1.366 g/cm³
• LogP: 2.80080
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 205.085126602
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

99%, ^*data from raw suppliers

2-(5-Nitro-1H-indol-3-yl)ethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=CN2)CCN
• Uses: 2-(5-Nitro-1H-indol-3-yl)ethanamine is used in the preparation of nitro/aminoindole analogs of serotonin.

Technology Process of 2-(5-nitro-1H-indol-3-yl)ethanamine

There total 7 articles about 2-(5-nitro-1H-indol-3-yl)ethanamine 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: 9.5%

2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide (393835-64-8) → 2-(5-nitro-1H-indol-3-yl) ethan-1-amine (55747-72-3)

Guidance literature:

2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide; With borane; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

With sodium carbonate; cesium fluoride; In ethanol; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2021.128081

Reference yield:

borane-THF + chloroform-methanol-ammonia + 2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide (393835-64-8) → 2-(5-nitro-1H-indol-3-yl) ethan-1-amine (55747-72-3)

Guidance literature:

sodium carbonate; cesium fluoride; In tetrahydrofuran; ethanol;

Reference yield:

3-(2-chloro-ethyl)-5-nitro-indole (858231-11-5) → 2-(5-nitro-1H-indol-3-yl) ethan-1-amine (55747-72-3)

Guidance literature:

With ammonium hydroxide; ethanol;

DOI:10.1021/ja01104a029

upstream raw materials:

3-(2-chloro-ethyl)-5-nitro-indole

2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide

5-nitro-L-tryptophane

tryptamine

Downstream raw materials:

N-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-acetamide

5-Aminotryptamine

Refernces

• 1、 Duguta, Govardhan,Muddam, Bhooshan,Kamatala, Chinna Rajanna,Utkoor, Umesh Kumar. "Trichloroisocyanuric acid (TCCA) and carboxamide interactions in TCCA/NaNO2 triggered nitration of pyrrole and indole in aqueous aprotic media: A kinetic correlation of solvent properties with reactivity". . p. 164 - 186. Retrieved 2020/10/02.
• 2、 -. "IDO inhibitors". Page/Page column 309; 310. . Retrieved 2018/09/02.