7-Nitroindole

Base Information

• Chemical Name: 7-Nitroindole
• CAS No.: 6960-42-5
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 29339900
• European Community (EC) Number: 677-504-8
• NSC Number: 69874
• DSSTox Substance ID: DTXSID20219879
• Nikkaji Number: J2.251I
• Wikidata: Q72494827
• ChEMBL ID: CHEMBL164632
• Mol file: 6960-42-5.mol

Synonyms:7-Nitroindole;7-Nitro-1H-indole;6960-42-5;1H-Indole, 7-nitro-;INDOLE, 7-NITRO-;NSC 69874;MFCD00005683;BRN 0130874;5-20-07-00044 (Beilstein Handbook Reference);7-nitro indole;NSC69874;7-Nitroindole, 97%;SCHEMBL259909;CHEMBL164632;DTXSID20219879;NSC-69874;STK249657;AKOS005207160;AB00500;AC-3141;CS-W001974;PS-5704;LS-83316;SY004017;A9204;AM20060938;FT-0621473;N0685;EN300-118948;N-3040;Z1255382963

Chemical Property of 7-Nitroindole

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Melting Point: 94-98 °C(lit.)
• Refractive Index: 1.723
• Boiling Point: 362.6 °C at 760 mmHg
• PKA: 13.96±0.30(Predicted)
• Flash Point: 173.1 °C
• PSA: 61.61000
• Density: 1.425 g/cm³
• LogP: 2.59930
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: slightly soluble
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

7-Nitroindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 68
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)[N+](=O)[O-])NC=C2
• Uses: 7-Nitroindole is a reagent used in chemical synthesis. It has been used in the synthesis of protein kinase and inosine monophosphate inhibitors, beta3 agonists and CCK-1 receptor modulators. 7-Nitroindole has also been used as a photochemical precursor of the 2'-deoxyribonolactone analog. 7-Nitroindole is a useful reactant for the preparation of various compounds and inhibitors. Reactant for preparation of:Protein kinase inhibitorsPotential fructose 1,6-bisphosphatase inhibitorsFactor Xa inhibitorsAntagonist of the mineralocorticoid receptorAntitumor sulfonamidesInosine monophosphate dehydrogenase (IMPDH) inhibitorsSubtype-selective cyclooxygenase (COX) inhibitorsThrombin protease-activated receptor (PAR-1) ligands

Technology Process of 7-Nitroindole

There total 14 articles about 7-Nitroindole 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%

7-nitro-1H-indole-3-carboxylic acid (1360891-19-5) → 7-nitro-1H-indole (6960-42-5)

Guidance literature:

In acetonitrile; at 140 ℃; Schlenk technique;

DOI:10.1080/00397911.2019.1703137

Reference yield: 90.0%

acetaldehyde (75-07-0,9002-91-9) + 2-nitro-aniline (88-74-4) → 7-nitro-1H-indole (6960-42-5)

Guidance literature:

With C₁₄H₂₂B₁₀Br₂FeN₂; In toluene; at 20 ℃; for 4h;

Reference yield: 86.0%

7-nitroindoline-2,3-dione (112656-95-8) → 7-nitro-1H-indole (6960-42-5)

Guidance literature:

With sodium tetrahydroborate; zirconium(IV) chloride; In tetrahydrofuran; at 20 ℃; for 18h; Temperature; Reagent/catalyst; Cooling with ice;

upstream raw materials:

7-nitro-1H-indole-2-carboxylic acid

vinyl magnesium bromide

1,2-Dinitrobenzene

ethyl 7-nitroindole-2-carboxylate

Downstream raw materials:

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(7-nitro-1H-indol-1-yl)acetoxy)ethyl)pyridine 1-oxide

1-tosyl-7-(trifluoromethyl)-1H-indole

1-tosyl-1H-indol-7-amine

1-[(4-methylphenyl)sulfonyl]-7-nitro-1H-indole

Refernces

• 1、 -. "Method for synthesizing 7-nitroindole". . . Retrieved 2020/03/09.
• 2、 Xiong, Li,Zhu, Xiao-Lei,Gao, Hua-Wei,Fu, Yu,Hu, Sheng-Quan,Jiang, Li-Na,Yang, Wen-Chao,Yang, Guang-Fu. "Discovery of Potent Succinate-Ubiquinone Oxidoreductase Inhibitors via Pharmacophore-linked Fragment Virtual Screening Approach". . p. 4830 - 4837. Retrieved 2016/07/06.