4583-55-5

Basic information

• Product Name: 5-Bromo-2,3-dimethylindole
• Synonyms: 5-Bromo-2,3-dimethylindole;5-broMo-2,3-diMethyl-1H-indole
• CAS NO: 4583-55-5
• Molecular Formula: C₁₀H₁₀BrN
• Molecular Weight: 224.11
• Mol File: 4583-55-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 136-137℃
• Boiling Point: 340.35 °C at 760 mmHg
• Flash Point: 159.638 °C
• Appearance: /
• Density: 1.487
• Refractive Index: 1.5923
• Storage Temp.: 2-8°C
• PKA: 16.91±0.30(Predicted)
• CAS DataBase Reference: 5-Bromo-2,3-dimethylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2,3-dimethylindole(4583-55-5)
• EPA Substance Registry System: 5-Bromo-2,3-dimethylindole(4583-55-5)

Safety Data

• Hazardous Substances Data: 4583-55-5(Hazardous Substances Data)

Usage

Uses

5-Bromo-2,3-dimethylindole is used to prepare 1-[(arylsulfonyl)amino]alkylindole derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists. It is also used to prepare modulators of secreted frizzled related protein-1 (SFRP-1).

InChI:InChI=1S/C10H10BrN/c1-6-7(2)12-10-4-3-8(11)5-9(6)10/h3-5,12H,1-2H3

Upstream product

• 4812-23-1 2-nitro-but-2-ene 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 78-93-3 butanone 
• 106-40-1 4-bromo-aniline 
• 1075-34-9 5-bromo-2-methyl-1H-indole 
• 27246-81-7 3-bromophenylhydrazine hydrochloride 
• 124-38-9 carbon dioxide 
• 589-21-9 (4-bromophenyl)hydrazine 
• 1417407-56-7 1-azido-4-bromo-2-(1-ethoxy-2-methylpropan-2-yl)benzene 
• 1417408-44-6 C₁₂H₁₈BrNO 
• 1417408-30-0 4-bromo-2-(1-ethoxy-2-methylpropan-2-yl)-1-nitrobenzene 
• 1417408-14-0 2-(5-bromo-2-nitrophenyl)-2-methylpropan-1-ol 
• 1417407-98-7 methyl 2-(5-bromo-2-nitrophenyl)-2-methylpropanoate 
• 598-30-1 sec.-butyllithium 

Downstream Products

• 29124-64-9 N-(2-acetyl-4-bromophenyl)acetamide 
• 1235481-55-6 1-(5-bromo-2,3-dimethyl-1H-indol-1-yl)-3-(phenylamino)propan-2-ol 
• 848749-82-6 5-bromo-2,3-dimethyl-1-(phenylmethyl)-1H-indole 

Relevant articles and documents

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One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles

A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode

The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.