Indole-3-carboxaldehyde

Base Information

• Chemical Name: Indole-3-carboxaldehyde
• CAS No.: 487-89-8
• Deprecated CAS: 246045-99-8
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 2933.99
• European Community (EC) Number: 207-665-8
• NSC Number: 10118
• UNII: 7FN04C32UO
• DSSTox Substance ID: DTXSID5060069
• Nikkaji Number: J26.057F
• Wikipedia: Indole-3-carboxaldehyde
• Wikidata: Q27103575
• Metabolomics Workbench ID: 44025
• ChEMBL ID: CHEMBL147741
• Mol file: 487-89-8.mol

Synonyms:3-indolemethanal;indole-3-aldehyde;indole-3-carbaldehyde;indole-3-carboxaldehyde

Chemical Property of Indole-3-carboxaldehyde

Chemical Property:

• Appearance/Colour: off-white to beige-brown crystalline powder
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Melting Point: 193-198 °C(lit.)
• Refractive Index: 1.729
• Boiling Point: 339.1 °C at 760 mmHg
• PKA: 15.50±0.30(Predicted)
• Flash Point: 166.8 °C
• PSA: 32.86000
• Density: 1.278 g/cm³
• LogP: 1.98040
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

Indole-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C=O
• Uses: Indole-3-carboxaldehyde is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group. It was also used as the starting material for the synthesis of higher order indoles including isoindolo[2,1-a]indoles, aplysinopsins, and 4-substituted-tetrahydrobenz[cd]indoles.

Technology Process of Indole-3-carboxaldehyde

There total 148 articles about Indole-3-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: 99.0%

1-pivaloyl-1H-indole-3-carbaldehyde (845619-73-0) → Indole-3-carboxaldehyde (487-89-8,1228547-52-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 40 - 45 ℃; for 2h;

DOI:10.1055/s-2004-836060

Reference yield: 98.0%

indole-3-carbinol (700-06-1) → Indole-3-carboxaldehyde (487-89-8,1228547-52-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; for 8h; Ambient temperature;

DOI:10.1021/jo00127a036

Reference yield: 97.0%

indole (120-72-9) + hexamethylenetetramine (100-97-0) → Indole-3-carboxaldehyde (487-89-8,1228547-52-1)

Guidance literature:

With iodine; oxygen; pyrographite; In N,N-dimethyl-formamide; at 120 ℃; for 0.8h; Reagent/catalyst; Solvent; Temperature; Time;

DOI:10.1016/j.tetlet.2017.05.050

upstream raw materials:

indole

chloroform

N,N-dimethyl-formamide

3-(Dimethylaminomethyl)indole

Downstream raw materials:

5-(3-indolylmethylene)hydantoin

(5Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one

5-(1H-indol-3-yl-methylene)-2-thioxo-thiazolidin-4-one

for 3e

Refernces

• 1、 Mandrekar, Ketan S.,Tilve, Santosh G.. "Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes". supporting information. p. 4152 - 4155. Retrieved 2021/03/15.
• 2、 Guo, Ying,Wang, Wei David,Li, Shengyu,Zhu, Yin,Wang, Xiaoyu,Liu, Xiao,Zhang, Yuan. "A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst". supporting information. p. 3689 - 3694. Retrieved 2021/09/29.