325800-39-3

Basic information

• Product Name: 5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: TERT-BUTYL 5-BROMO-3-FORMYL-1H-INDOLE-1-CARBOXYLATE;N-BOC-5-BROMO-3-FORMYLINDOLE;5-BROMOINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED;5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;5-Bromoindole-3-carboxaldehyde, N-BOC protected 98%;1-Boc-5-bromo-3-formylindole;Zinc02563715;5-Bromo-1H-indole-3-carboxaldehyde, N-BOC protected 98%
• CAS NO: 325800-39-3
• Molecular Formula: C₁₄H₁₄BrNO₃
• Molecular Weight: 324.17
• EINECS: 604-604-1
• Product Categories: Aldehyde;Indole;Organohalides
• Mol File: 325800-39-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 426.7 °C at 760 mmHg
• Flash Point: 211.9 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 1.73E-07mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(325800-39-3)
• EPA Substance Registry System: 5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(325800-39-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 325800-39-3(Hazardous Substances Data)

Usage

General Description

5-Bromo-3-formylindole-1-carboxylic acid tert-butyl ester is a chemical compound that belongs to the class of indole derivatives. It is a potent and selective inhibitor of peptidyl-prolyl cis/trans isomerase Pin1, which plays a crucial role in various cellular processes including cell cycle regulation, oncogenesis, and neurodegeneration. 5-BROMO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is commonly used in research laboratories as a tool compound for studying the biological functions of Pin1 and for drug discovery related to Pin1 inhibitors. It has potential therapeutic applications in the treatment of cancer and neurodegenerative diseases.

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

Upstream product

• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 395643-15-9 methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-tert-butoxycarbonyl-5-bromo)indol]acrylate 
• 905710-14-7 tert-butyl 5-bromo-3-(hydroxymethyl)-1H-indole-1-carboxylate 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 395643-16-0 (S)-5-bromo-1-tert-butoxycarbonyl-N^α-benzyloxycarbonyl-tryptophan methyl ester 
• 395643-17-1 (R)-5-bromo-1-tert-butoxycarbonyl-N^α-benzyloxycarbonyl-tryptophan methyl ester 

Relevant articles and documents

Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins

Electrophilic aromatic substitution is one of the most thoroughly studied reactions in organic chemistry. In the present paper, the 5-brominated spirobrassinol methyl ethers VII, VIII were obtained by electrophilic substitution of the aromatic core of indoline at the C-5 position in the presence of various brominating agents. The same products were also prepared from 5-bromoindole (IX) following the sequence for the synthesis 1-methoxyspirobrassinol methyl ether (V) from indoline. In addition, the new related 5-bromospiroindoline derivatives XX-XXIII were synthesised and their biological activity on human tumour cell lines was examined. The presence of bromine in the indole or indoline skeleton at the C-5 position resulted in the partial increase in anticancer activity on leukaemia cell lines (Jurkat, CEM). The structures of the newly prepared products were determined by 1H and 13C NMR spectroscopy, including HSQC, HMBC, COSY, NOESY and DEPT measurements.

Indole-substituted hydrazide derivatives and uses thereof

The invention discloses indole-substituted hydrazide derivatives and a use thereof, concretely relates to novel indole-substituted hydrazide derivatives and a medicinal composition including the abovecompounds, a use of the derivatives and the medicinal composition in the protection of nerve cells, and also relates to a method for preparing the compounds and the medicinal composition, and a use of the compounds and the medicinal composition in the preparation of drugs for treating diseases associated with glutamate excitotoxicity and oxidative stress damage or free radicals, or neurodegenerative diseases, especially the Alzheimer disease.

Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones

The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β- trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.