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
• General Description: 7-Nitroindole is an intermediate compound synthesized through the decarboxylation of 7-nitroindole-2-carboxylic acid using S,S-dimethylacetamide and a copper salt catalyst. It plays a key role in the synthesis of 7-amino-DL-tryptophan, demonstrating its utility as a precursor in organic and pharmaceutical chemistry. The improved decarboxylation method offers a more efficient and straightforward approach compared to traditional techniques.

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:

7-aminoindole

1-(2'-Deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentafuranosyl)-7-nitroindole

7-nitro-3-chloro-1H-indole

3-acetyl-7-nitro-1H-indole

Refernces

An Improved Method for Decarboxylating Indole-2-Carboxylic Acids and Its Application in the Synthesis of 7-Amino-DL-Tryptophan

10.1139/v64-189

The study presents an improved method for decarboxylating indole-2-carboxylic acids, specifically focusing on the synthesis of 7-amino-DL-tryptophan. Key chemicals involved include 7-nitroindole-2-carboxylic acid, which is decarboxylated using S,S-dimethylacetamide and a copper salt catalyst to produce 7-nitroindole. This compound serves as an intermediate in the synthesis of 7-amino-DL-tryptophan. Other intermediates like 7-nitrogranzine and ethyl a-acetamido-a-carbethoxy-α-(7-amino-5-indolyl)propionate are also synthesized and reduced to obtain the final product. The study highlights the efficiency and simplicity of the dimethylacetamide method for decarboxylation compared to the conventional quinoline procedure.