2-(5-nitro-1H-indol-3-yl)-2-oxoacetic acid

Base Information

• Chemical Name: 2-(5-nitro-1H-indol-3-yl)-2-oxoacetic acid
• CAS No.: 6953-39-5
• Molecular Formula: C10H6 N2 O5
• Molecular Weight: 234.165
• NSC Number: 71258
• DSSTox Substance ID: DTXSID10989498
• Wikidata: Q82978641
• Mol file: 6953-39-5.mol

Synonyms:6953-39-5;2-(5-nitro-1H-indol-3-yl)-2-oxoacetic acid;2-(5-Nitro-3-indolyl)-2-oxoacetic Acid;(5-nitro-1h-indol-3-yl)(oxo)acetic acid;NSC71258;DTXSID10989498;AC6639;MFCD11205784;NSC-71258;AKOS005919941;SY058698;CS-0364699;A914577

Chemical Property of 2-(5-nitro-1H-indol-3-yl)-2-oxoacetic acid

Chemical Property:

• Vapor Pressure: 4.1E-11mmHg at 25°C
• Boiling Point: 507.3°Cat760mmHg
• Flash Point: 260.6°C
• Density: 1.674g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 234.02767130
• Heavy Atom Count: 17
• Complexity: 364

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=CN2)C(=O)C(=O)O

Technology Process of 2-(5-nitro-1H-indol-3-yl)-2-oxoacetic acid

There total 5 articles about 2-(5-nitro-1H-indol-3-yl)-2-oxoacetic 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:

1-(5-nitro-1H-indol-3-yl)ethan-1-one (4771-10-2) → (5-nitro-indol-3-yl)glyoxylyl acid (6953-39-5)

Guidance literature:

With pyridine; selenium(IV) oxide; at 100 ℃; for 10h;

DOI:10.1016/j.fitote.2018.06.003

Reference yield:

2-(5-nitro-1H-indol-3-yl)-2-oxoacetyl chloride (6953-35-1) → (5-nitro-indol-3-yl)glyoxylyl acid (6953-39-5)

Guidance literature:

With potassium hydroxide; In water; at 90 ℃; for 1h;

DOI:10.1135/cccc20060899

Reference yield:

5-nitroindole (6146-52-7) → (5-nitro-indol-3-yl)glyoxylyl acid (6953-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / diethyl ether / 24 h / 0 °C

2: KOH / H₂O / 1 h / 90 °C

With potassium hydroxide; In diethyl ether; water;

DOI:10.1135/cccc20060899

upstream raw materials:

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

5-nitroindole

oxalyl dichloride

1-(5-nitro-1H-indol-3-yl)ethan-1-one

Downstream raw materials:

5-nitro-1H-indole-3-carboxylic acid

N-benzyl-2-(1-methyl-5-nitro-1H-indol-3-yl)acetamide

C₁₇H₁₅N₃O₃

2-(5-nitro-1 H-indol-3-yl)acetic acid

Refernces

• 1、 Zhu, Shaolin,MacMillan, David W. C.. "Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade". supporting information; experimental part. p. 10815 - 10818. Retrieved 2012/08/07.