5-Nitroindole

Base Information

• Chemical Name: 5-Nitroindole
• CAS No.: 6146-52-7
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 2933.99
• European Community (EC) Number: 228-153-0
• NSC Number: 520594
• UNII: O2BHX6EDBN
• DSSTox Substance ID: DTXSID80210403
• Nikkaji Number: J2.242J
• Wikidata: Q27285232
• ChEMBL ID: CHEMBL164651
• Mol file: 6146-52-7.mol

Synonyms:5-nitroindole;NSC 520594

Chemical Property of 5-Nitroindole

Chemical Property:

• Appearance/Colour: Yellow-green cyrstalline solid
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Melting Point: 141-143 °C
• Refractive Index: 1.723
• Boiling Point: 362.6 °C at 760 mmHg
• PKA: 15.25±0.30(Predicted)
• Flash Point: 173.1 °C
• PSA: 61.61000
• Density: 1.425 g/cm³
• LogP: 2.59930
• Storage Temp.: -20°C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 2.5
• 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:

97%min, ^*data from raw suppliers

5-Nitroindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-41
• Safety Statements: 26-39-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1=CC2=C(C=CN2)C=C1[N+](=O)[O-]
• Uses: Reactant for preparation of:? ;Pharmaceutically active 2-oxo-1-pyrrolidine analogues1? ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators2? ;Protein Kinase Inhibitors and antiproliferative agents3? ;Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)4? ;Antifungal agents5? ;Cannabinoid receptor type 1 (CB1) antagonists6? ;Potential anticancer agents7? ;Potential antivascular agents8? ;Selective Anti-leukemic agents9? ;Anti human immunodeficiency virus subtype 1 ( 5-Nitroindole (cas# 6146-52-7) is a compound useful in organic synthesis. Reactant for preparation of:Pharmaceutically active 2-oxo-1-pyrrolidine analoguesTryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsProtein Kinase Inhibitors and antiproliferative agentsPositive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)Antifungal agentsCannabinoid receptor type 1 (CB1) antagonistsPotential anticancer agentsPotential antivascular agentsSelective Anti-leukemic agentsAnti human immunodeficiency virus subtype 1 (HIV-1) agents

Technology Process of 5-Nitroindole

There total 35 articles about 5-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: 100.0%

5-nitro-2,3-dihydro-1H-indole (32692-19-6) → 5-nitroindole (6146-52-7)

Guidance literature:

With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen; In ethyl acetate; at 70 ℃; for 46h; under 760.051 Torr; Sealed tube;

DOI:10.1002/chem.202001961

Reference yield: 99.0%

5-nitroindole-1-carboxylic acid tert-butyl ester (166104-19-4) → 5-nitroindole (6146-52-7)

Guidance literature:

In various solvent(s); at 150 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1080/00397910802238718

Reference yield: 98.0%

5-nitro-1-(phenylsulfonyl)-1H-indole (124400-51-7) → 5-nitroindole (6146-52-7)

Guidance literature:

With sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0029-1219918

upstream raw materials:

5-nitro-2,3-dihydro-1H-indole

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

1-ethenyl-2-pyrrolidinone

2-bromo-4-nitroaniline

Downstream raw materials:

5-Nitro-3-(4-nitro-phenylsulfanyl)-1H-indole

2-(5-nitro-1H-indol-3-yl)-2-oxoacetyl chloride

1-(4-fluorophenyl)-5-nitro-1H-indole

4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester

Refernces

• 1、 Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi. "Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes". supporting information. p. 15793 - 15798. Retrieved 2020/10/12.
• 2、 Abinaya, R.,Baskar, B.,Mariappan, M.,Prasanth, Arun,Sridhar, R.,Srinath, S.. "Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products". . p. 2575 - 2587. Retrieved 2020/05/13.