Indole-4-carboxaldehyde

Base Information

• Chemical Name: Indole-4-carboxaldehyde
• CAS No.: 1074-86-8
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29333990
• European Community (EC) Number: 625-162-5
• NSC Number: 337264
• DSSTox Substance ID: DTXSID40318838
• Nikkaji Number: J1.412.229J
• Wikidata: Q72482968
• Metabolomics Workbench ID: 156946
• Mol file: 1074-86-8.mol

Synonyms:Indole-4-carboxaldehyde;1074-86-8;1H-Indole-4-carbaldehyde;4-Formylindole;1H-Indole-4-carboxaldehyde;indole-4-carbaldehyde;4-Indole-carboxaldehyde;4-Indolecarbaldehyde;4-Formyl-1H-indole;MFCD01632221;INDOLE-4-ALDEHYDE;NSC 337264;4-formyl-indole;1H-indol-4-carbaldehyde;4-formylindol;4-indolealdehyde;4-formyl indole;NSC337264;4-indolcarboxaldehyde;indol-4-carboaldehyde;indole 4carboxaldehyde;indol 4-carboxaldehyde;indole 4-carboxaldehyde;1H-indole-4-carbaldehyd;SCHEMBL97761;1H-Indole-4-carbaldehyde #;Indole-4-carboxaldehyde, 97%;1H- Indole- 4- carboxaldehyde;SCHEMBL10257427;DTXSID40318838;CHEBI:143235;AM688;HMS3650A21;STK292737;AKOS000265263;AB09519;BS-3817;CS-W001288;NSC-337264;NCGC00329124-01;AC-23426;SY013097;A2081;FT-0633301;I0712;EN300-66992;I-2202;1H-indole-4-carbaldehyde;AB01323273-02;SR-01000946761;SR-01000946761-1;Z1065768492

Chemical Property of Indole-4-carboxaldehyde

Chemical Property:

• Appearance/Colour: Straw yellow or brown powder
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Melting Point: 139-143 °C(lit.)
• Refractive Index: 1.729
• Boiling Point: 339.1 °C at 760 mmHg
• PKA: 15.84±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
• Water Solubility.: Soluble in ethanol and acetone. Insoluble in water.
• XLogP3: 2.2
• 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-4-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C2C=CNC2=C1)C=O
• Uses: Indole-4-carboxaldehyde is usually used as reactant in Biginelli reaction,preparation of antitumor agents,intramolecular Friedel-Crafts acylation,preparation of inhibitors of cell division in E. Coli,synthesis of Hantzsch pyridine-containing Schiff bases. 4-Indolecarbaldehyde is a synthetic intermediate used for pharmaceutical synthesis. Also used as reactant in Biginelli reaction, synthesis of aurora kinase A inhibitors, preparation of antitumor agents, intermolecular Friedel-Crafts acylation, preparation of inhibitors of cell division in E. coli and synthesis of Hantzsch pyridine-containing Schiff bases.

Technology Process of Indole-4-carboxaldehyde

There total 40 articles about Indole-4-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: 91.0%

4-cyanoindole (16136-52-0) → 4-formyl indole (1074-86-8)

Guidance literature:

With sodium hypophosphite; nickel; In pyridine; water; acetic acid; at 45 - 50 ℃; for 2h;

DOI:10.1016/S0040-4020(01)88608-7

Reference yield: 90.4%

(1H-indol-4-yl)methanol (1074-85-7) → 4-formyl indole (1074-86-8)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jo01304a043

Reference yield: 88.0%

5-amino-2-cyanomethylisoquinolinium bromide → 4-formyl indole (1074-86-8)

Guidance literature:

With acetic acid butyl ester; sodium hydrogensulfite; sodium sulfite; for 72h; Heating;

DOI:10.1002/jhet.5570370545

upstream raw materials:

(1H-indol-4-yl)methanol

4-bromo-1H-indole

N,N-dimethyl-formamide

4-cyanoindole

Downstream raw materials:

4-(2-nitroethenyl)-1H-indole

4-vinylindole

E/Z-4-(2-phenylethenyl)-1H-indole

4-methyl-1H-indole

Refernces

• 1、 Konishi, Hideyuki,Kumon, Minoru,Yamaguchi, Miyuki,Manabe, Kei. "Palladium-catalyzed external-CO-free reductive carbonylation of aryl sulfonates". . . Retrieved 2020/10/29.
• 2、 -. "THERAPEUTIC AGENTS, AND METHODS OF MAKING AND USING THE SAME". Page/Page column 161-162. . Retrieved 2010/11/27.