23073-31-6

Basic information

• Product Name: 4-FLUORO-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 4-FLUORO-3-FORMYLINDOLE;4-FLUORO-1H-INDOLE-3-CARBALDEHYDE;4-FLUOROINDOLE-3-ALDEHYDE;4-FLUOROINDOLE-3-CARBOXALDEHYDE;1H-Indole-3-carboxaldehyde, 4-fluoro-;4-Fluoro-1H-indole-3-carboxaldehyde;4-fluoro-3-carboxaldehyde;4-Fluoro-1H-indol-3-carbaldehyde
• CAS NO: 23073-31-6
• Molecular Formula: C₉H₆FNO
• Molecular Weight: 163.15
• EINECS: 200-589-5
• Mol File: 23073-31-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 342.423°C at 760 mmHg
• Flash Point: 160.892°C
• Appearance: /
• Density: 1.385±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.695
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.90±0.30(Predicted)
• CAS DataBase Reference: 4-FLUORO-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUORO-1H-INDOLE-3-CARBALDEHYDE(23073-31-6)
• EPA Substance Registry System: 4-FLUORO-1H-INDOLE-3-CARBALDEHYDE(23073-31-6)

Safety Data

• Hazardous Substances Data: 23073-31-6(Hazardous Substances Data)

Usage

General Description

4-Fluoro-1H-Indole-3-carbaldehyde is a chemical compound classified under the heterocyclic aromatic organic class, specifically an indole. Its molecular formula is C9H6FNO. It is also known by synonyms such as 3-Formyl-4-fluoroindole and 4-Fluoroindole-3-carboxaldehyde. Possessing an aromatic ring structure, the compound contains a fluoro substituent, which is an important functional group that greatly influences its chemical properties. It is often used in pharmaceutical research and chemical synthesis due to its potential as a synthetic intermediate. Its exact physical properties might vary depending on the supplier, including its appearance, boiling point, melting point, and solubility. As with many chemicals, proper handling and safety measures should be observed.

InChI:InChI=1/C9H6FNO/c10-7-2-1-3-8-9(7)6(5-12)4-11-8/h1-5,11H

Upstream product

• 387-43-9 4-fluoroindole 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 863407-47-0 trans-3-[4-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide 
• 1011484-22-2 4-fluoro-3-methyl-1H-indole 
• 1428969-91-8 1-(4-fluoro-1H-indol-3-yl)-2-((3-methoxy-phenyl)amino)-2-phenylethanone 
• 1422432-53-8 C₂₁H₁₆FN₃O₃ 
• 1422433-16-6 C₂₃H₂₀FN₃O₃ 
• 1369570-99-9 (3S,6R)-3-((4-fluoro-1-tosyl-3-indolyl)methyl)-3,6-dihydro-6-isopropyl-2,5-dimethoxypyrazine 
• 1369570-96-6 3-bromomethyl-4-fluoro-1-tosylindole 
• 1369570-94-4 4-fluoro-3-hydroxymethyl-1-tosylindole 
• 1369571-01-6 (S)-1-tosyl-4-fluorotryptophan methyl ester 
• 110221-04-0 (S)-2-amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid 
• 863407-42-5 [4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde 

Relevant articles and documents

Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure-Activity Relationships and Membrane Targeting Properties

Antibacterials that disrupt cell membrane function have the potential to eradicate “persister” organisms and delay the emergence of resistance. Here we report the antimycobacterial activities of 4-fluoro and 6-methoxyindoles bearing a cationic amphiphilic motif represented by a lipophilic n-octyl side chain at position 1 and a positively charged azepanyl or 1,4-dioxa-8-azaspiro[4.5]decane moiety at position 3. These analogues exhibited balanced profiles of potency (Mycobacterium bovis BCG, M tuberculosis H37Rv), selective activity, solubility, and metabolic stability. Bacteriological mechanism of action investigations on a representative analogue revealed cell membrane permeabilization and depolarization in M bovis BCG. These membrane-related changes preceded cell death indicating that the loss in membrane integrity was not an epiphenomenon. Bactericidal activity was observed against both growing and nongrowing mycobacterial cultures. The analogue also upregulated cell envelope stress-inducible promoters piniBAC and pclgR, implicating the involvement of envelope-related targets in its mode of action.

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)