98600-34-1

Basic information

• Product Name: 4-Bromoindole-3-carboxaldehyde
• Synonyms: 4-BROMO-1H-INDOLE-3-CARBALDEHYDE;4-BROMOINDOLE-3-CARBOXYALDEHYDE;4-BROMOINDOLE-3-CARBOXALDEHYDE;4-BROMO-3-INDOLECARBALDEHYDE;4-BROMO-3-FORMYLINDOLE;4-Bromoindole-3-carbaldehyde;4-Bromoindole-3-carboxaldehyde 98%;4-BROMO-3-FORMYL-1H-INDOLE
• CAS NO: 98600-34-1
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Product Categories: Indole;Aldehyde;Building Blocks;Indoles;Simple Indoles
• Mol File: 98600-34-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 179-180°C
• Boiling Point: 395.6 °C at 760 mmHg
• Flash Point: 193 °C
• Appearance: /Solid
• Density: 1.727 g/cm³
• Vapor Pressure: 1.82E-06mmHg at 25°C
• Refractive Index: 1.752
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.57±0.30(Predicted)
• CAS DataBase Reference: 4-Bromoindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromoindole-3-carboxaldehyde(98600-34-1)
• EPA Substance Registry System: 4-Bromoindole-3-carboxaldehyde(98600-34-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21/22-36/37/38-36-22
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 98600-34-1(Hazardous Substances Data)

Usage

General Description

4-Bromoindole-3-carboxaldehyde is a chemical compound with the molecular formula C9H6BrNO. It is a derivative of indole, which is a heterocyclic organic compound. 4-Bromoindole-3-carboxaldehyde is commonly used as a building block for the synthesis of various pharmaceuticals and fine chemicals. It has been studied for its potential use in the development of novel drugs and has been investigated for its biological activities, including its potential anti-cancer properties. The compound can be produced through various synthetic methods and is available for purchase from chemical suppliers for research and industrial purposes.

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

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 52488-36-5 4-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 181271-32-9 4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 100-97-0 hexamethylenetetramine 
• 64258-88-4 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 1280538-41-1 C₁₂H₁₃BrN₂O₂ 
• 101909-43-7 4-bromo-1H-indole-3-carboxylic acid methyl ester 
• 101909-45-9 4-bromo-1-methoxycarbonylindole 
• 942-24-5 3-methoxycarbonylindole 

Downstream Products

• 338760-45-5 4-bromo-1-methyl-1H-indole-3-carbaldehyde 
• 1339939-29-5 ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate 
• 1354659-25-8 C₃₄H₃₈N₂O₇S₂ 
• 1448345-04-7 (4-bromo-1-(phenylsulfonyl)-1H-indol-3-yl)methanol 
• 1448345-13-8 C₁₆H₁₃BrN₂O₅S 
• 1448344-64-6 (4-bromo-1-(phenylsulfonyl)-1H-indol-3-yl)methyl 2,4-dichlorobenzoyloxycarbamate 
• 1448344-82-8 (2R,3S)-4-bromo-2'-oxo-1-(phenylsulfonyl)spiro[indoline-3,4'-oxazolidine]-2-yl 2,4-dichlorobenzoate 
• 1448344-86-2 C₁₅H₁₀BrNO₃S 
• 1631136-26-9 C₂₈H₂₉BrN₂O 
• 959236-12-5 4-(trifluoromethyl)-1H-indole-3-carbaldehyde 
• 101909-43-7 4-bromo-1H-indole-3-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of indiacen A using a practical one-pot reaction: Promoted by a key waste product, and its utility in natural products synthesis

Trialkylammonium salt, recognized as a waste product in the Heck reaction, was found to act as a key catalyst in the practical one-pot Heck-dehydration reaction. A concise synthesis of indiacen A was accomplished in 92% overall yield using a protecting-gr

Pd(II)-Catalyzed Transient Directing Group-Assisted Regioselective Diverse C4-H Functionalizations of Indoles

The development of a rational strategy for achieving site-selective C4-H halogenation of indoles is an appealing yet challenging task. Herein, we disclose a Pd(II)-catalyzed transient directing group (TDG)-assisted methodology for realizing C4 chlorination/bromination of indoles employing glycine as the TDG and NFSI as a bystanding oxidant. The use of inexpensive and commercially available CuX2as the halide source is the key highlight of this protocol. Furthermore, the TDG methodology was also extended to accessing C4 acetoxylated indoles employing acetic acid as the acetate source and 1-fluoro-2,4,6-trimethylpyridinium triflate as the oxidant.

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.