19005-93-7 | 1H-Indole-2-carbaldehyde

Packsize	Purity	Availability	Price	Discounted Price
100mg	97%	in stock	$6.00	$4.00
250mg	97%	in stock	$7.00	$5.00
1g	97%	in stock	$16.00	$11.00
5g	≥97%	in stock	$70.00	$49.00
25g	98%	in stock	$236.00	$166.00
100g	98%	in stock	$870.00	$609.00

Description

• Catalog Number: AB11624
• Chemical Name: 1H-Indole-2-carbaldehyde
• CAS Number: 19005-93-7
• Molecular Formula: C9H7NO
• Molecular Weight: 145.1580
• MDL Number: MFCD03001425
• SMILES: O=Cc1cc2c([nH]1)cccc2
• NSC Number: 71792

Computed Properties

• Complexity: 158
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 2.2

Upstream Synthesis Route

The synthesis of 1H-indole-2-carbaldehyde can be achieved through several methods, however one common upstream synthetic route is as follows:

1. Begin with 2-aminobenzaldehyde as the starting material.
2. Undergo Fischer indole synthesis by reacting 2-aminobenzaldehyde with phenylhydrazine to produce the indole core structure.
3. The resultant indole is then functionalized at the 2-position by introducing a formyl group through Vilsmeier-Haack formylation, using reagents such as phosphorus oxychloride (POCl3) and N,N-dimethylformamide (DMF).
4. Careful work-up, typically involving hydrolysis and neutralization steps, will yield the desired 1H-indole-2-carbaldehyde.

Further purification may be required to obtain the compound in high purity, such as recrystallization or column chromatography. This synthetic route allows for the introduction of substituents at different positions of the indole ring system if needed for specific applications.

Literature

• Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.

  Organic letters 20120907

• Addition of indoles to oxyallyl cations for facile access to α-indole carbonyl compounds.

  Organic letters 20120406

• Synthesis and characterization of neutral luminescent diphosphine pyrrole- and indole-aldimine copper(I) complexes.

  Inorganic chemistry 20110801

• 'One-pot' multicomponent approach to indolizines and pyrido[1,2-a]indoles.

  Organic letters 20110520

• 3,4,5-Trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide-1H-indole-2-carbaldehyde azine-methanol (2/1/2).

  Acta crystallographica. Section E, Structure reports online 20100101

• Design, synthesis, and evaluation of inhibitors for severe acute respiratory syndrome 3C-like protease based on phthalhydrazide ketones or heteroaromatic esters.

  Journal of medicinal chemistry 20070419

• Carbazolothiophene-2-carboxylic acid derivatives as endothelin receptor antagonists.

  Bioorganic & medicinal chemistry letters 20040308

• Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists.

  Bioorganic & medicinal chemistry 20030306

• [Antihypoxic and antiedemic activity of new condensed indole derivatives].

  Eksperimental'naia i klinicheskaia farmakologiia 20020101