934-05-4

Basic information

• Product Name: Methyl 4-bromopyrrole-2-carboxylate
• Synonyms: METHYL 4-BROMOPYRROLE-2-CARBOXYLATE;METHYL 4-BROMO-1H-PYRROLE-2-CARBOXYLATE;RARECHEM AL BF 1264;4-Bromo-2-(methoxycarbonyl)-1H-pyrrole;Methyl 4-BroMopyrrole-2-carboxylate, 97+%
• CAS NO: 934-05-4
• Molecular Formula: C₆H₆BrNO₂
• Molecular Weight: 204.02
• Product Categories: pharmacetical;Esters;Pyrroles & Indoles;API intermediates;Heterocycle intermediates;Benzenes;Pyrroles & Indoles
• Mol File: 934-05-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 100-101°C
• Boiling Point: 290.5 °C at 760 mmHg
• Flash Point: 129.5 °C
• Appearance: /
• Density: 1.674 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 13.49±0.50(Predicted)
• CAS DataBase Reference: Methyl 4-bromopyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-bromopyrrole-2-carboxylate(934-05-4)
• EPA Substance Registry System: Methyl 4-bromopyrrole-2-carboxylate(934-05-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 934-05-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

4-Bromo-1H-pyrrole-2-carboxylic Acid Methyl Ester is a useful synthetic intermediate. It is used to synthesize potent melanin-concentrating hormone (MCH-R1) antagonists based on pyrazolopiperazinone.

InChI:InChI=1/C6H6BrNO2/c1-10-6(9)5-2-4(7)3-8-5/h2-3,8H,1H3

Upstream product

• 67-56-1 methanol 
• 72652-32-5 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone 
• 110-86-1 pyridine 
• 192197-56-1 4-bromo-1H-pyrrole-2-carboxylic acid chloride 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 124-41-4 sodium methylate 
• 1193-62-0 methyl Pyrrole-2-carboxylate 

Downstream Products

• 86288-94-0 4-Bromo-1-((E)-styryl)-1H-pyrrole-2-carboxylic acid 
• 157425-54-2 5-acetyl-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester 
• 156237-78-4 4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 86288-56-4 4-Bromo-1-phenethyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 86288-62-2 4-Bromo-1-phenethyl-1H-pyrrole-2-carboxylic acid 
• 86288-67-7 4-Bromo-1-phenethyl-1H-pyrrole-2-carbonyl chloride 
• 941714-50-7 4-bromo-1-(5-fluoro-2-nitro-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 1448612-55-2 methyl 5-[1-[4-(2-aminopyrimidin-5-yl)phenyl]cyclobutyl]-4-bromo-1H-pyrrole-2-carboxylate 
• 1208361-39-0 1-amino-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester 
• 1221419-65-3 6-(5-chloropyridin-2-yl)-3-[4-(2-cyclopropyl-2-hydroxy-ethoxy)-3-methoxy-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one 
• 1221419-66-4 6-(5-chloropyridin-2-yl)-3-[4-(3-hydroxy-pyrrolidin-1-yl)-3-methoxy-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one 
• 1221419-84-6 6-(5-chloropyridin-2-yl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 
• 1221419-68-6 6-(5-chloropyrimidin-2-yl)-3-[4-(2-cyclopropyl-2-hydroxy-ethoxy)-3-methoxy-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one 
• 1221420-16-1 6-bromo-3-(3,4-dimethoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 

Relevant articles and documents

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Non-basic azolotriazinone MCHR1 antagonists for the treatment of obesity: An empirical brain-exposures-driven candidate selection for in vivo efficacy studies

Non-basic azolotriazinones were explored using an empirical free brain exposures-driven approach to identify potent MCHR1 antagonists for evaluation in in vivo efficacy studies. An optimized lead from this series, 1j (rMCHR1 Ki = 1.8 nM), demonstrated a 6.9% reduction in weight gain relative to vehicle in a rat model at 30 mg/kg after 4 days of once-daily oral treatment as a glycine prodrug. Despite a promising efficacy profile, an assessment of the biliary toxicity risk of this compound rendered this compound non-progressible.

Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles

Bromoperoxidases from the brown alga Ascophyllum nodosum, abbreviated as VBrPO(AnI) and VBrPO(AnII), show 41% sequence homology and differ by a factor of two in the percentage of α-helical secondary structures. Protein monomers organize into homodimers for VBrPO(AnI) and hexamers for VBrPO(AnII). Bromoperoxidase II binds hydrogen peroxide and bromide by approximately one order of magnitude stronger than VBrPO(AnI). In oxidation catalysis, bromoperoxidases I and II turn over hydrogen peroxide and bromide similarly fast, yielding in morpholine-4-ethanesulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon-bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with larger energy gaps between the π-type HOMO of, for example, an alkene and the σ*Br,X-type LUMO of the bromination reagent. By using this approach, the reactivity of substrates and selectivity for carbon-bromine bond formation in reactions mediated by vanadate-dependent bromoperoxidases become predictable, as exemplified by the synthesis of bromopyrroles occurring naturally in marine sponges of the genera Agelas, Acanthella, and Axinella. The Royal Society of Chemistry.