115666-21-2

Basic information

• Product Name: 7-BROMO-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 7-BROMO-1H-INDOLE-3-CARBALDEHYDE;7-BROMO-3-FORMYLINDOLE;1H-Indole-3-carboxaldehyde, 7-bromo-;7-Bromo-3-indolecarboxaldehyde;7-Bromoindole-3-carbaldehyde;7-Bromo-1H-indole-3-carboxaldehyde
• CAS NO: 115666-21-2
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Product Categories: Indole;Organohalides;Building Blocks;C7 to C10;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;New Products for Chemical Synthesis
• Mol File: 115666-21-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 165-172℃
• Boiling Point: 395.6±22.0 °C(Predicted)
• Appearance: /
• Density: 1.727±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.84±0.30(Predicted)
• CAS DataBase Reference: 7-BROMO-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-1H-INDOLE-3-CARBALDEHYDE(115666-21-2)
• EPA Substance Registry System: 7-BROMO-1H-INDOLE-3-CARBALDEHYDE(115666-21-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 115666-21-2(Hazardous Substances Data)

Usage

General Description

7-Bromo-1H-indole-3-carbaldehyde is a chemical compound with the molecular formula C9H6BrNO. It is a derivative of indole, a heterocyclic aromatic organic compound. The presence of a bromine atom and an aldehyde functional group on the indole ring gives this compound unique chemical properties. 7-Bromo-1H-indole-3-carbaldehyde has applications in organic synthesis, particularly in the preparation of pharmacologically active molecules and other bioactive compounds. It is also used as a building block in the synthesis of various pharmaceuticals and agrochemicals, making it a valuable intermediate in the field of medicinal chemistry and chemical research.

Upstream product

• 51417-51-7 7-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 298-12-4 Glyoxilic acid 
• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 
• 20780-74-9 7-bromoisatin 
• 101080-38-0 N-(2-bromophenyl)-2-isonitrosoacetanilide 
• 615-36-1 2-bromoaniline 
• 852391-39-0 (7-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 331646-98-1 8-bromo-1H-benzo[d][1,3]oxazine-2,4-dione 
• 40619-69-0 2-(7-bromo-1H-indole-3-yl)ethylamine 
• 86915-22-2 7-bromo-3-methyl-1H-indole 
• 210569-78-1 C₂₀H₂₁BBrN₃O₄ 
• 210569-79-2 N-[(3-bromobenzylcarbamoyl)methyl]-3-(7-bromo-3H-indol-3-yl)propionamide 
• 642073-58-3 N-Boc-3-iodo-Tyr(Bn)-Leu-7-bromo-Trp-OMe 
• 642073-57-2 N-Boc-3-iodo-Tyr(Bn)-AIa-7-bromo-Trp-OMe 
• 642073-60-7 N-Boc-3-iodo-Tyr(Me)-Leu-7-bromo-Trp-OMe 

Relevant articles and documents

Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid

Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.

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.

Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure

A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.