7-Nitroindole-2-carboxylic acid

Base Information

• Chemical Name: 7-Nitroindole-2-carboxylic acid
• CAS No.: 6960-45-8
• Molecular Formula: C9H6N2O4
• Molecular Weight: 206.158
• Hs Code.: 2933990090
• European Community (EC) Number: 230-154-6
• NSC Number: 69877
• DSSTox Substance ID: DTXSID7064520
• Nikkaji Number: J266.002D
• Wikidata: Q72494862
• ChEMBL ID: CHEMBL1870764
• Mol file: 6960-45-8.mol

Synonyms:7-nitro-1H-indole-2-carboxylic acid;CRT 0044876;CRT-0044876;CRT0044876

Chemical Property of 7-Nitroindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: brown powder
• Vapor Pressure: 1.13E-11mmHg at 25°C
• Melting Point: 260-261 °C
• Refractive Index: 1.5570 (estimate)
• Boiling Point: 520.8 °C at 760 mmHg
• PKA: 4.03±0.30(Predicted)
• Flash Point: 268.8 °C
• PSA: 98.91000
• Density: 1.632 g/cm³
• LogP: 2.29750
• Storage Temp.: room temp
• Solubility.: DMSO: >20mg/mL
• Water Solubility.: Insoluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 206.03275668
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

7-Nitro-1H-indole-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-21/22-43-36
• Safety Statements: 36/37/39-26-22-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)[N+](=O)[O-])NC(=C2)C(=O)O
• General Description: 7-Nitroindole-2-carboxylic acid is a key intermediate used in the synthesis of 7-amino-DL-tryptophan, where it undergoes decarboxylation facilitated by S,S-dimethylacetamide and a copper salt catalyst to form 7-nitroindole. This process demonstrates the utility of the dimethylacetamide method as an efficient and simplified alternative to traditional decarboxylation techniques, such as the quinoline procedure. 7-Nitroindole-2-carboxylic acid plays a pivotal role in the multistep synthesis pathway, ultimately contributing to the production of biologically relevant tryptophan derivatives.

Technology Process of 7-Nitroindole-2-carboxylic acid

There total 5 articles about 7-Nitroindole-2-carboxylic acid 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: 99.0%

7-nitro-1H-indole-2-carboxylic acid methyl ester (167027-28-3) → 7-nitro-1H-indole-2-carboxylic acid (6960-45-8)

Guidance literature:

7-nitro-1H-indole-2-carboxylic acid methyl ester; With sodium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; water; Product distribution / selectivity;

Reference yield: 96.0%

ethyl 7-nitroindole-2-carboxylate (6960-46-9) → 7-nitro-1H-indole-2-carboxylic acid (6960-45-8)

Guidance literature:

ethyl 7-nitroindole-2-carboxylate; With water; potassium hydroxide; In ethanol; at 40 ℃;

With hydrogenchloride; In ethanol; water;

Reference yield:

2-(2-(2-nitrophenyl)hydrazono)propionic acid ethyl ester (292853-66-8) → 7-nitro-1H-indole-2-carboxylic acid (6960-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: polyphosphoric acid

2: aq.-ethanolic KOH

With potassium hydroxide; PPA;

DOI:10.1021/ja01550a052

upstream raw materials:

ethyl 7-nitroindole-2-carboxylate

2-(2-(2-nitrophenyl)hydrazono)propionic acid ethyl ester

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

o-nitrophenylhydrazine hydrochloride

Downstream raw materials:

7-nitro-1H-indole

7-nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

2,2-dimethyl-propionic acid (R)-3-(4-methoxy-benzylsulfanyl)-2-[(7-nitro-1H-indole-2-carbonyl)-amino]-propyl ester

N-(5,8-dimethyl-9H-carbazol-1-yl)-N-ethyl-4-methoxybenzenesulfonamide

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.