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HomeProduct name listIndole-4-carboxaldehyde

Indole-4-carboxaldehyde

Synonym(s):4-Formylindole;NSC 337264

  • CAS NO.:1074-86-8
  • Empirical Formula: C9H7NO
  • Molecular Weight: 145.16
  • MDL number: MFCD01632221
  • EINECS: 625-162-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-01 13:44:44
Indole-4-carboxaldehyde Structural

What is Indole-4-carboxaldehyde?

Chemical properties

White to dark brown solid

The Uses of Indole-4-carboxaldehyde

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.

The Uses of Indole-4-carboxaldehyde

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.

What are the applications of Application

4-formyl Indole is a synthetic intermediate

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ChEBI: Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group.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]+.

Properties of Indole-4-carboxaldehyde

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
CAS DataBase Reference 1074-86-8(CAS DataBase Reference)
NIST Chemistry Reference 1H-indole-4-carboxaldehyde(1074-86-8)

Safety information for Indole-4-carboxaldehyde

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Indole-4-carboxaldehyde

InChIKey JFDDFGLNZWNJTK-UHFFFAOYSA-N
SMILES N1C2=C(C(C=O)=CC=C2)C=C1

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