3-Indoleglyoxylic acid

Base Information

• Chemical Name: 3-Indoleglyoxylic acid
• CAS No.: 1477-49-2
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.17
• Hs Code.: 2918300090
• European Community (EC) Number: 216-029-9
• NSC Number: 71954
• UNII: 34U8W7RF8Q
• DSSTox Substance ID: DTXSID2074536
• Nikkaji Number: J103.828A
• Wikidata: Q72483010
• ChEMBL ID: CHEMBL57285
• Mol file: 1477-49-2.mol

Synonyms:indole-3-glyoxylic acid

Chemical Property of 3-Indoleglyoxylic acid

Chemical Property:

• Appearance/Colour: yellow microcrystalline powder
• Vapor Pressure: 1.46E-07mmHg at 25°C
• Melting Point: 217 °C (dec.)(lit.)
• Refractive Index: 1.711
• Boiling Point: 413 °C at 760 mmHg
• Flash Point: 203.6 °C
• PSA: 70.16000
• Density: 1.477 g/cm³
• LogP: 1.43520
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 189.042593085
• Heavy Atom Count: 14
• Complexity: 264

Purity/Quality:

97% ^*data from raw suppliers

Indole-3-glyoxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)C(=O)O
• Uses: Reactant for synthesis of fenbufen and ethacrynic acid derivatives Reactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agents Reactant for synthesis of tertiary amides Reactant for preparation of fuconojirimycin derivatives as inhibitors of α-Fucosidases Reactant for total synthesis of oxazinin-3 from 3-indoleglyoxylic acid via an intramolecular addition/cyclization reactions Indole-3-glyoxylic Acid is a compound used in the preparation of various indoleglyoxylates as inhibitors of sortase A and isocitrate lyase.

Technology Process of 3-Indoleglyoxylic acid

There total 13 articles about 3-Indoleglyoxylic 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: 92.0%

indole (120-72-9) + oxalyl dichloride (79-37-8) → 3-indolylglyoxylic acid (1477-49-2)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 0.833333h;

DOI:10.3390/ph10030062

Reference yield: 63.0%

(4-hydroxy-phenylimino)-(1H-indol-3-yl)-acetonitrile (477935-11-8) → 3-indolylglyoxylic acid (1477-49-2)

Guidance literature:

With hydrogenchloride; at 20 ℃;

DOI:10.1016/S0040-4039(02)00799-2

Reference yield:

3-acetylindole (703-80-0) → 3-indolylglyoxylic acid (1477-49-2)

Guidance literature:

With pyridine; selenium(IV) oxide;

DOI:10.1016/j.tetlet.2013.05.095

upstream raw materials:

indolyl-3-glyoxylyl chloride

ethyl 2-(1H-indol-3-yl)-2-oxoacetate

1-(1,2-Dioxo-2-(3-indolyl)ethyl)indole

indole

Downstream raw materials:

5-(3-indolylmethylene)hydantoin

indole-3-acetic acid

Indole-3-carboxaldehyde

2-(3-indolyl)oxoacetic acid methyl ester