773873-77-1

Basic information

• Product Name: 5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 1H-Indole-3-carboxylicacid,5-broMo-,Methylester;Methyl 5-BroMoindole-3-carboxylate;5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER;METHYL 5-BROMO-1H-INDOLE-3-CARBOXYLATE;RARECHEM AL BF 0374
• CAS NO: 773873-77-1
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08
• EINECS: 221-862-6
• Mol File: 773873-77-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 386.2 °C at 760 mmHg
• Flash Point: 187.3 °C
• Appearance: /
• Density: 1.629 g/cm³
• Vapor Pressure: 3.61E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER(773873-77-1)
• EPA Substance Registry System: 5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER(773873-77-1)

Safety Data

• Hazardous Substances Data: 773873-77-1(Hazardous Substances Data)

Usage

General Description

5-Bromo-1H-indole-3-carboxylic acid methyl ester is a chemical compound that belongs to the class of indole derivatives. It is a methyl ester of 5-bromo-1H-indole-3-carboxylic acid, which is commonly used in the synthesis of various pharmaceuticals and agrochemicals. 5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER has potential applications in the field of medicinal chemistry and drug discovery due to its structural features and pharmacological properties. It is also used as a building block in the synthesis of diverse biologically active compounds. The presence of the bromine atom in its structure makes it a versatile substrate for further synthetic modifications, making it valuable for chemical research and development.

InChI:InChI=1/C10H8BrNO2/c1-14-10(13)8-5-12-9-3-2-6(11)4-7(8)9/h2-5,12H,1H3

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 67-56-1 methanol 
• 10406-06-1 5-bromo-1H-indole-3-carboxylic acid 
• 1336879-56-1 2,2,2-trichloro-1-(5-bromo-1H-indol-3-yl)ethan-1-one 
• 10075-50-0 5-bromo-1H-indole 
• 1262150-42-4 (Z)-methyl 3-[(4-bromophenyl)amino]acrylate 
• 106-40-1 4-bromo-aniline 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 163083-67-8 1-Benzyl-5-bromo-1H-indole-3-carboxylic acid methyl ester 
• 400071-95-6 5-bromo-1-methyl-1H-indole-3-carboxylic acid 
• 1445963-16-5 1-(3-(9-bromo-2-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-ylamino)propyl)-3-phenylurea 
• 1445963-15-4 methyl 9-bromo-5-methyl-11-(3-(3-phenylureido)propylamino)-5H-indolo[2,3-b]quinoline-2-carboxylate 
• 1421349-51-0 methyl 5-bromo-2-((4-(methoxycarbonyl)phenyl)(methyl)amino)-1H-indole-3-carboxylate 
• 1421349-52-1 methyl 5-bromo-2-((4-chlorophenyl)(methyl)amino)-1H-indole-3-carboxylate 

Relevant articles and documents

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

1,3,4-Oxadiazole-2(3H)-thione Analogs as PIM Kinase Inhibitors

Proviral integration site for moloney murine leukemia virus (PIM) kinases are highly expressed in hematological cancers. They phosphorylate downstream substrates that contribute to tumor growth and survival. Therefore, a potent inhibitor of PIM kinases is expected to be effective at treating hematological cancers. In the present study, several indole derivatives of 1,3,4-oxadiazole-2(3H)-thione were synthesized and evaluated as PIM kinase inhibitors. Structure–activity relationship studies yielded potent inhibitors of all three PIM kinases in the single-digit to low double-digit nanomolar IC50 range. Kinase profiling of a representative compound showed high selectivity among 15 other kinases.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.