17826-04-9

Basic information

• Product Name: 6-Bromoindole-3-carboxaldehyde
• Synonyms: 6-BROMOINDOLE-3-CARBOXALDEHYDE;6-BROMO-1H-INDOLE-3-CARBALDEHYDE;6-BROMO-1H-INDOLE-3-CARBOXALDEHYDE;6-BROMO-3-FORMYL-1H-INDOLE;6-BROMO-3-FORMYLINDOLE;6-Bromo-1H-indole-3-carbaldehyde, 6-Bromo-3-formylindole;6-broMo-3-carboxaldehyde
• CAS NO: 17826-04-9
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• EINECS: 241-867-7
• Product Categories: Indole;Aldehyde;Building Blocks;Indoles;Simple Indoles
• Mol File: 17826-04-9.mol

Chemical Properties

• Melting Point: 202-206 °C
• Boiling Point: 395.6°Cat760mmHg
• Flash Point: 193°C
• Appearance: /Solid
• Density: 1.727g/cm³
• Vapor Pressure: 0.0767mmHg at 25°C
• Refractive Index: 1.411
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.57±0.30(Predicted)
• CAS DataBase Reference: 6-Bromoindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoindole-3-carboxaldehyde(17826-04-9)
• EPA Substance Registry System: 6-Bromoindole-3-carboxaldehyde(17826-04-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• Hazardous Substances Data: 17826-04-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromoindole-3-carboxaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its reactivity in organic reactions. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Bromoindole-3-carboxaldehyde is utilized as a building block for the creation of a wide range of organic compounds. Its versatility in undergoing various chemical reactions makes it a valuable component in the synthesis of complex organic molecules.
Used in Research and Development:
6-Bromoindole-3-carboxaldehyde is employed as a research chemical in academic and industrial laboratories. It aids scientists in understanding the structure-activity relationships of indole-based compounds and contributes to the discovery of new chemical entities with potential applications in various fields.

InChI:InChI=1/C10H30O3Si4/c1-14(2,3)11-17(10,12-15(4,5)6)13-16(7,8)9/h1-10H3

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 

Downstream Products

• 134419-23-1 penaresin methyl ester 
• 158991-81-2 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde 
• 224434-83-7 6-bromo-1H-indole-3-carbonitrile 
• 354538-27-5 6-bromo-1-tosyl-3-vinyl-1H-indole 
• 354538-26-4 (S)-1-(N-tosyl-6-bromoindol-3-yl)-1,2-ethanediol 
• 1026187-62-1 2-azido-1-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethylamine 
• 354538-34-4 (R)-2-azido-2-(N-tosyl-6-bromoindol-3-yl)-1-ethanol 
• 354538-30-0 (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol 
• 354538-32-2 (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane 
• 354538-36-6 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-azidoethylamine 
• 354538-35-5 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine 
• 354538-37-7 (R)-3-(6-bromoindol-3-yl)-6-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 
• 354538-23-1 (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide 
• 210569-73-6 C₂₀H₂₁BBrN₃O₄ 

Relevant articles and documents

6-bromoindole-3-carbaldehyde, from an Acinetobacter Sp. Bacterium associated with the ascidian Stomozoa murrayi

The ascidian Stomozoa murrayi from Caribbean coral reefs is not overgrown by macroepibionts. Chemical extraction of this organism gave 6-bromoindole-3-carbaldehyde (1) and its debromo analog (2). These two compounds, previously obtained from several marine organisms, were also extracted from an Acinetobacter sp. bacterium isolated from the surface of S. murrayi. Compound 1 exhibits in vitro settlement inhibition of barnacle larvae, moderate antibacterial properties, but not antialgal or fish-feeding deterrent activities. Its potential role in contributing to the reduced fouling in S. murrayi is proposed.

Structure-activity relationship for bromoindole carbaldehydes: Effects on the sea urchin embryo cell cycle

Natural derivatives of indole-3-carbaldehyde were isolated from the tropical marine ascidian Stomoza murrayi. A series of 13 derivatives, three natural and 10 synthetic (brominated and N-methylated), were examined for their effects on cell division of sea urchin eggs. These derivatives were shown to inhibit the first mitotic cycle in a concentration-dependent manner. By comparing the IC50 values with the structure of the various molecules, we were able to determine that bromination increased the cytotoxicity of the compound with a maximum occurring when bromine was added to carbon number 2, while addition of N-methylation was shown to markedly reduce the cytotoxicity of these same compounds brominated at carbon 2 only. Biological activity of this family of compounds has been characterized, via detailed study of addition of the most active derivative, 2,5,6-tribromoindole-3-carbaldehyde, on macromolecule synthesis and cytoskeleton reorganization during the first mitotic cycle of fertilized sea urchin eggs. Fluorescence localization of chromatin and microtubules revealed that 2,5,6-tribromoindole-3-carbaldehyde allowed pronuclei migration and fusion but prevented the condensation of chromatin, nuclear envelope breakdown, and bipolar mitotic spindle assembly, inducing an arrest of sea urchin embryogenesis at the beginning of mitosis. It is postulated here that this phenotype is likely to be due to a strong inhibition of DNA replication and protein synthesis.