303041-88-5

Basic information

• Product Name: 4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 4-BROMOINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED;4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-BROMO-3-FORMYLINDOLE, N-BOC PROTECTED;4-Bromo-1H-indole-3-carboxaldehyde, N-BOC protected 98%;4-Bromo-3-formyl-1H-indole, N-BOC protected;tert-butyl 4-bromo-3-formyl-1H-indole-1-carboxylate;4-Bromo-1H-indole-3-carboxaldehyde, N-BOC protected;1-Boc-4-bromo-3-formylindole
• CAS NO: 303041-88-5
• Molecular Formula: C₁₄H₁₄BrNO₃
• Molecular Weight: 324.17
• Product Categories: API intermediates
• Mol File: 303041-88-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 426.7°Cat760mmHg
• Flash Point: 211.9°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 1.73E-07mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(303041-88-5)
• EPA Substance Registry System: 4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(303041-88-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 303041-88-5(Hazardous Substances Data)

Usage

General Description

4-Bromo-3-formylindole-1-carboxylic acid tert-butyl ester is a chemical compound that consists of a bromine atom, a formyl group, and an indole ring. It also has a carboxylic acid group and a tert-butyl ester group attached to the indole ring. 4-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is commonly used in organic synthesis for the production of pharmaceuticals and other fine chemicals. Its tert-butyl ester group provides stability and protection for the carboxylic acid, allowing for controlled release of the acid under specific conditions. The bromine and formyl groups also offer reactivity and functionalization potential, making it a valuable building block in chemical synthesis.

InChI:InChI=1/C14H14BrNO3/c1-14(2,3)19-13(18)16-7-9(8-17)12-10(15)5-4-6-11(12)16/h4-8H,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 98600-34-1 4-bromo-1H-indole-3-carbaldehyde 
• 52488-36-5 4-bromo-1H-indole 

Downstream Products

• 866270-11-3 (S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide 
• 914349-05-6 tert-butyl 4-bromo-3-(hydroxymethyl)-1H-indole-1-carboxylate 

Relevant articles and documents

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.

ANTIBACTERIAL COMPOUNDS

Novel compounds having antimicrobial activitiy, in particular against Pseudomonas aeruginosa, Burkholderia cepaciaand/or Clostridium difficile, and a pharmaceutical composition containing the novel compound.

A Modular Formal Total Synthesis of (±)-Cycloclavine

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).