Indole-5-carboxaldehyde

Base Information

• Chemical Name: Indole-5-carboxaldehyde
• CAS No.: 1196-69-6
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29339900
• Mol file: 1196-69-6.mol

Synonyms:Indole-5-carboxaldehyde;1H-Indole-5-carboxaldehyde;5-Formylindole;

Chemical Property of Indole-5-carboxaldehyde

Chemical Property:

• Appearance/Colour: red crystalline powder
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Melting Point: 100-103 ºC
• Refractive Index: 1.729
• Boiling Point: 339.1 ºC at 760 mmHg
• PKA: 16.14±0.30(Predicted)
• Flash Point: 166.8 ºC
• PSA: 32.86000
• Density: 1.278 g/cm³
• LogP: 1.98040
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: DMSO, Methanol
• Water Solubility.: Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

Indole-5-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents 1 Reactant in preparation of analogs of botulinum neurotoxin serotype A protease inhibitors 2 Reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes 3 Reactant in synthesis of para-para stilbenophanes by McMurry coupling 4 Reactant in stereoselective synthesis of heteroaromatic (E)-α,β-unsaturated ketones from aldehydes 5 Reactant in structure-based drug design of aurora kinase A inhibitors. Indole-5-carboxaldehyde is used as a reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents; and in synthesis of para-para stilbenophanes by McMurry coupling. It is also used as a reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes and in structure-based drug design of aurora kinase A inhibitors.

Technology Process of Indole-5-carboxaldehyde

There total 25 articles about Indole-5-carboxaldehyde 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: 96.0%

indole-5-methanol (1075-25-8) → 1H-indole-5-carboxaldehyde (1196-69-6)

Guidance literature:

With manganase oxide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2004.09.056

Reference yield: 95.0%

indole (120-72-9) + formic acid ethyl ester (109-94-4) → 1H-indole-5-carboxaldehyde (1196-69-6)

Guidance literature:

indole; formic acid ethyl ester; at 35 - 45 ℃; for 1h; Inert atmosphere;

With zinc(II) chloride; at 45 - 55 ℃; for 12h; Reagent/catalyst; Inert atmosphere;

Reference yield: 91.0%

5-(1,3-dioxolan-2-yl)-1H-indole (152879-74-8) → 1H-indole-5-carboxaldehyde (1196-69-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1002/jhet.5570420121

upstream raw materials:

5-bromo-1H-indole

N,N-dimethyl-formamide

indole-5-methanol

1H-Indole-5-carboxylic acid

Downstream raw materials:

C₁₆H₁₂N₂O₂

(Z)-3-(1H-Indol-5-yl)-2-methoxy-acrylic acid benzyl ester

5-(1H-imidazol-2-yl)-1-(phenylsulfonyl)-1H-indole

1-(phenylsulfonyl)-5-(1-(phenylsulfonyl)-1H-imidazol-2-yl)-1H-indole

Refernces

• 1、 Holoidovsky, Lara,Meijler, Michael M.. "Synthesis and Evaluation of Indole-Based Autoinducers on Quorum Sensing in Vibrio cholerae". . p. 572 - 576. Retrieved 2020/04/30.
• 2、 Cao, Hualiang,Pu, Weiwen,Zhang, Jie,Yan, Peijun,Zhang, Jun,Xu, Sheng. "Decarboxylative formylation of aryl halides with glyoxylic acid by palladium catalysis under oxygen". supporting information. p. 1287 - 1290. Retrieved 2020/08/21.