3-(2-Nitrovinyl)-1H-indole

Base Information

• Chemical Name: 3-(2-Nitrovinyl)-1H-indole
• CAS No.: 3156-51-2
• Molecular Formula: C10H8N2O2
• Molecular Weight: 188.186
• Hs Code.: 2933990090
• European Community (EC) Number: 636-532-0
• NSC Number: 81232
• Nikkaji Number: J991.762D,J996.325A
• Wikidata: Q76144214
• ChEMBL ID: CHEMBL594624
• Mol file: 3156-51-2.mol

Synonyms:3-(2-Nitrovinyl)-1H-indole;3156-51-2;3-(2-NITROVINYL)INDOLE;3-[(E)-2-Nitroethenyl]-1H-indole;51870-94-1;(E)-3-(2-nitrovinyl)-1H-indole;3-[(E)-2-nitrovinyl]-1H-indole;3-[(1E)-2-nitroethenyl]-1H-indole;3-(2-nitroethenyl)-1H-indole;3-[(E)-2-nitroeth-1-enyl]-1H-indole;NSC81232;3-(2-nitrovinyl)-indole;Cambridge id 5106706;CHEMBL594624;AMY27832;MFCD00022748;NSC-81232;3-[(E)-2-nitro-vinyl]-1H-indole;AKOS000291490;AKOS017475241;1H-Indole, 3-[(E)-2-nitroethenyl]-;3-[(E)-2-Nitroethenyl]-1H-indole #;NCGC00336768-01;C91022;N-8300;AB01221024-03;EN300-1848305;A875863

Chemical Property of 3-(2-Nitrovinyl)-1H-indole

Chemical Property:

• Vapor Pressure: 1.95E-06mmHg at 25°C
• Refractive Index: 1.734
• Boiling Point: 406.1 °C at 760 mmHg
• Flash Point: 199.4 °C
• PSA: 61.61000
• Density: 1.352 g/cm³
• LogP: 2.93850
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 188.058577502
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

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

3-(2-NITROVINYL)INDOLE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C=C[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)/C=C/[N+](=O)[O-]

Technology Process of 3-(2-Nitrovinyl)-1H-indole

There total 16 articles about 3-(2-Nitrovinyl)-1H-indole 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: 98.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + nitromethane (75-52-5) → 3-(2-nitroethenyl)-1H-indole (3156-51-2)

Guidance literature:

With ammonium acetate; at 128 - 130 ℃;

DOI:10.1039/b714743k

Reference yield: 95.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + nitromethane (75-52-5) → 3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2,51870-94-1)

Guidance literature:

With ammonium acetate; In benzene; Reflux;

DOI:10.1039/c7ra13207g

Reference yield: 92.0%

indole (120-72-9) + 1-dimethylamino-2-nitroethene (73430-27-0,87446-70-6,1190-92-7) → 3-(2-nitroethenyl)-1H-indole (3156-51-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.08333h;

DOI:10.3987/COM-10-S(E)125

upstream raw materials:

Indole-3-carboxaldehyde

nitromethane

indole

1-dimethylamino-2-nitroethene

Downstream raw materials:

NSC 49095

tryptamine

indole

3-nitroquinoline

Refernces

• 1、 Viaud,Rollin. "First synthesis of an indole glucosinolate". . p. 1417 - 1418. Retrieved 1990.
• 2、 Kandekar, Somnath,Preet, Ranjan,Kashyap, Maneesh,Prasad M. U., Renu,Mohapatra, Purusottam,Das, Dipon,Satapathy, Shakti Ranjan,Siddharth, Sumit,Jain, Vaibhav,Choudhuri, Maitrayee,Kundu, Chanakya N.,Guchhait, Sankar K.,Bharatam, Prasad V.. "Structural elaboration of a natural product: Identification of 3,3′-diindolylmethane aminophosphonate and urea derivatives as potent anticancer agents". . p. 1873 - 1884. Retrieved 2013.
• 3、 -. "Application of alkaloid streptindole and derivatives thereof in prevention and control of plant viruses and pathogenic bacteria". Paragraph 0016; 0030-0031. . Retrieved 2021/07/01.
• 4、 M?hler, Jasper S.,Schnitzer, Tobias,Wennemers, Helma. "Amine Catalysis with Substrates Bearing N-Heterocyclic Moieties Enabled by Control over the Enamine Pyramidalization Direction". supporting information. p. 15623 - 15628. Retrieved 2020/10/29.