Indole-4-carboxaldehyde Chemical Properties

Melting point:

139-143 °C(lit.)

Boiling point:

339.1±15.0 °C(Predicted)

Density 

1.278±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml

pka

15.84±0.30(Predicted)

form 

powder to crystal

color 

Light yellow to Brown

Water Solubility 

Soluble in ethanol and acetone. Insoluble in water.

Sensitive 

Air Sensitive

InChI

InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H

InChIKey

JFDDFGLNZWNJTK-UHFFFAOYSA-N

SMILES

N1C2=C(C(C=O)=CC=C2)C=C1

CAS DataBase Reference

1074-86-8(CAS DataBase Reference)

NIST Chemistry Reference

1H-indole-4-carboxaldehyde(1074-86-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-43

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

Indole-4-carboxaldehyde Usage And Synthesis

Chemical Properties

White to dark brown solid

Uses

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.

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.

Definition

ChEBI: Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group. It has a role as an algal metabolite. It is a member of indoles and a heteroarenecarbaldehyde.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1752, 1981 DOI: 10.1021/jo00321a053
Tetrahedron, 39, p. 3695, 1983 DOI: 10.1016/S0040-4020(01)88608-7

General Description

Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.

Synthesis

Tetrapropylammonium perruthenate (0.3 g, 0.85 mmol) was added in portions to a mixture of alcohol product from 1H-Indole-4-Methanol (2.5 g, 17 mmol), N-methylmorpholine N-oxide (3.0 g, 25 mmol) and 4 A molecular sieves (3.0 g) in anhydrous methylene chloride (30 mL) at room temperature. The mixture was stirred at room temperature under nitrogen for 1 h and then filtered. The filtrate was concentrated in vacuo, and the residue was purified by chromatography (SiO2, CH2Cl2) to provide Indole-4-carboxaldehyde as a white powder (2.0 g, 80percent): 1H NMR (300 MHz, CDCl3) δ10.2 (s, 1H), 8.52 (br s, 1H), 7.64-7.69 (m, 2H), 7.31-7.44 (m, 3H), CI MS m/z=146 [C9H7NO+H]+.

Indole-4-carboxaldehyde(1074-86-8)Related Product Information

• Indole-3-butyric acid
• Indometacin
• Formaldehyde
• Indole-3-acetic acid
• 3-FORMYLINDOLE,3-Indole Carboxaldehyde Indole-3-Carboxaldehyde,INDOLE-3-CARBOXALDEHYDE,1h-indole-3-carboxaldehyde
• Indole
• 3-Cyanoindole
• Indoline-2-carboxylic acid
• Indole-4-boronic acid pinacol ester
• 3-Indoleacetonitrile
• DL-INDOLE-3-LACTIC ACID
• Methyl 3-cyanoindole-4-carboxylate
• 3-formyl-1H-Indole-4-carboxylic acid methyl ester
• Indol-1-yl-acetic acid
• 3-Indoleacrylic acid
• Indole-4-carboxylic acid
• 7-FORMYLINDOLE,INDOLE-7-CARBOXALDEHYDE
• Methyl indole-4-carboxylate