72000-67-0

Basic information

• Product Name: 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione
• Synonyms: 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione;3-bromo-1-phenyl-3-pyrroline-2,5-quinone;3-bromo-1-phenyl-pyrrole-2,5-dione;3-bromo-1-phenylpyrrole-2,5-dione;NSC523909
• CAS NO: 72000-67-0
• Molecular Formula: C₁₀H₆BrNO₂
• Molecular Weight: 252.06414
• Mol File: 72000-67-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 326.5°Cat760mmHg
• Flash Point: 151.3°C
• Appearance: /
• Density: 1.767g/cm³
• Vapor Pressure: 0.000215mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione(72000-67-0)
• EPA Substance Registry System: 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione(72000-67-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 72000-67-0(Hazardous Substances Data)

Usage

General Description

3-Bromo-1-phenyl-1H-pyrrole-2,5-dione is a chemical compound with the molecular formula C10H6BrNO2. It is an organic compound that consists of a phenyl group attached to a pyrrole-2,5-dione ring with a bromine atom at the 3-position. 3-Bromo-1-phenyl-1H-pyrrole-2,5-dione is used in organic synthesis and medicinal chemistry as a building block for various pharmaceuticals and bioactive molecules. It has potential applications in the development of therapeutic agents for various diseases and conditions. Additionally, it is also used as a reagent in organic reactions to introduce the 3-bromo-1-phenyl-1H-pyrrole-2,5-dione moiety into other molecules for further functionalization.

InChI:InChI=1/C10H6BrNO2/c11-8-6-9(13)12(10(8)14)7-4-2-1-3-5-7/h1-6H

Upstream product

• 902269-81-2 2,3-dibromo-N-phenyl-succinamic acid 
• 58879-90-6 3,4-dibromo-1-phenylpyrrolidine-2,5-dione 
• 75-36-5 acetyl chloride 
• 941-69-5 N-phenyl-maleimide 
• 62-53-3 aniline 
• 5926-51-2 bromomaleic anhydride 
• 65833-14-9 3,4-dibromo-2,5-dihydro-1-phenyl-1H-pyrrole-2,5-dione 
• 37902-58-2 3-phenylcarbamoylacrylic acid 

Downstream Products

• 144040-36-8 2-(N-methylanilino)-N-phenylmaleimide 
• 92884-55-4 N-(4-bromophenyl)-2-bromomaleimide 
• 65833-14-9 3,4-dibromo-2,5-dihydro-1-phenyl-1H-pyrrole-2,5-dione 
• 113709-99-2 4-Hydroxy-1,1'-diphenyl-[3,3']bipyrrolyl-2,5,2',5'-tetraone 
• 558473-96-4 2-methoxy-N-phenylmaleimide 
• 558473-98-6 2-ethoxy-N-phenylmaleimide 
• 558473-99-7 2-methoxymaleanilic acid 
• 558474-00-3 2-ethoxymaleanilic acid 
• 200574-69-2 5-(methoxymethyl)-N-phenyl-2,3-pyridinedicarboximide 
• 1206838-01-8 C₁₅H₁₂BrNO₂ 
• 1258849-42-1 3-(2-nitrophenyl)-1-phenyl-1H-pyrrole-2,5-dione 
• 1353013-51-0 3-(hex-1-yn-1-yl)-1-phenyl-1H-pyrrole-2,5-dione 
• 1266664-87-2 3-hexylsulfanyl-1-phenyl-pyrrole-2,5-dione 
• 1375329-86-4 3-(2-hexylsulfanyl-2-phenyl-ethyl)-1-phenyl-pyrrole-2,5-dione 

Relevant articles and documents

Copper-catalysed bromoamination of maleimides using NBS as the bromine source

CuBr2-catalysed bromoamination of maleimides has been achieved in THF with alkylamines and N-bromosuccinimide as nitrogen and bromine sources respectively. The reaction conditions were optimised. A series of bromoamination products such as 3-am

A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents

A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.

Stable and Rapid Thiol Bioconjugation by Light-Triggered Thiomaleimide Ring Hydrolysis

Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2NHiPr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis. UV irradiation of thiol bioconjugates formed with this photocaged maleimide unleashes rapid thiomaleimide ring hydrolysis to yield the desired stable conjugates within 1 h under gentle, ice-cold conditions.