877-03-2

Basic information

• Product Name: 5-Bromoindole-3-carboxaldehyde
• Synonyms: TIMTEC-BB SBB010081;5-BROMOINDOLE-3-ALDEHYDE;5-BROMOINDOLE-3-CARBOXALDEHYDE;5-BROMOINDOLE-3-CARBOXYALDEHYDE;5-BROMO-1H-INDOLE-3-CARBALDEHYDE;5-BROMO-1H-INDOLE-3-CARBOXALDEHYDE;5-BROMO-3-FORMYLINDOLE;5-bromoindole-3-carbaldehyde
• CAS NO: 877-03-2
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• EINECS: 212-884-7
• Product Categories: Indoles and derivatives;Aldehydes;Pyrroles & Indoles;Indole;Aldehyde;Organohalides;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks
• Mol File: 877-03-2.mol
• Article Data: 87

Chemical Properties

• Melting Point: 204-207 °C(lit.)
• Boiling Point: 395.6 °C at 760 mmHg
• Flash Point: 193 °C
• Appearance: Beige to brown/Crystalline Powder
• Density: 1.727 g/cm³
• Vapor Pressure: 1.82E-06mmHg at 25°C
• Refractive Index: 1.752
• Storage Temp.: Room temperature.
• PKA: 14.54±0.30(Predicted)
• BRN: 124725
• CAS DataBase Reference: 5-Bromoindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoindole-3-carboxaldehyde(877-03-2)
• EPA Substance Registry System: 5-Bromoindole-3-carboxaldehyde(877-03-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 877-03-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6BrNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 325800-39-3 5-bromo-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde 
• 16382-11-9 ethyl 2-[2-(4-bromophenyl)hydrazinylidene]propanoate 
• 92557-51-2 5-Bromo-indole-3-carbinol 
• 298-12-4 Glyoxilic acid 
• 1310-73-2 sodium hydroxide 
• 50-00-0 formaldehyd 
• 81387-89-5 3,5-dibromo-1H-indole 
• 100-97-0 hexamethylenetetramine 
• 830-93-3 N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine 
• 79-37-8 oxalyl dichloride 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 26807-69-2 N-acetylindololine-2-sulfonic acid sodium 

Downstream Products

• 92423-68-2 3-Carboxymethyl-5-(5-brom-indolyl-(3)-methylen)-rhodanin 
• 93657-40-0 5-(5-bromo-indol-3-ylmethylene)-3-phenyl-2-thioxo-thiazolidin-4-one 
• 90271-86-6 5-bromo-1H-indole-3-carbonitrile 
• 5030-96-6 bis(5-bromo-1H-indol-3-yl)methane 
• 339282-64-3 3-(tert-butyloxycarbonylaminomethyl)-5-bromoindole 
• 1370714-01-4 3-(1-benzyl-5-bromo-1H-indol-3-yl)-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 1215174-60-9 3,4,5-trihydroxy-N'-[(5-bromo-1H-indol-3-yl)methylidene]benzohydrazide 
• 1417917-00-0 C₁₈H₁₁BrN₂O₂ 
• 1417616-00-2 C₁₇H₁₃BrN₂O₄S 
• 1417616-12-6 (S)-2-((R)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal 
• 1417616-13-7 (2S,3R)-3-(5-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal 
• 1417616-14-8 (S)-2-((R)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-heptanal 
• 1417616-15-9 (S)-2-((R)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)octanal 
• 158991-80-1 5-bromo-N-(1-p-toluenesulphonylindole)-3-carboxaldehyde 

Relevant articles and documents

(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols

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Design, Synthesis, and Biological Evaluation of Novel 3-Aminomethylindole Derivatives as Potential Multifunctional Anti-Inflammatory and Neurotrophic Agents

The development of multifunctional molecules that are able to simultaneously interact with several pathological components has been considered as a solution to treat the complex pathologies of neurodegenerative diseases. Herein, a series of aminomethylindole derivatives were synthesized, and evaluation of their application for antineuroinflammation and promoting neurite outgrowth was disclosed. Our initial screening showed that most of the compounds potently inhibited lipopolysaccharide (LPS)-stimulated production of NO in microglial cells and potentiated the action of NGF to promote neurite outgrowth of PC12 cells. Interestingly, with outstanding NO/TNF-α production inhibition and neurite outgrowth-promoting activities, compounds 8c and 8g were capable of rescuing cells after injury by H2O2. Their antineuroinflammatory effects were associated with the downregulation of the LPS-induced expression of the inflammatory mediators inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Western blotting and immunofluorescence assay results indicated that the mechanism of their antineuroinflammatory actions involved suppression of the MAPK/NF-κB signal pathways. Further studies revealed that another important reason for the high comprehensive antineuroinflammatory activity was the anti-COX-2 capabilities of the compounds. All these results suggest that the potential biochemical multifunctional profiles of the aminomethylindole derivatives provide a new sight for the treatment of neurodegenerative diseases.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.