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

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

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

Upstream product

• 37902-58-2 3-phenylcarbamoylacrylic acid 
• 65833-14-9 3,4-dibromo-2,5-dihydro-1-phenyl-1H-pyrrole-2,5-dione 
• 5926-51-2 bromomaleic anhydride 
• 62-53-3 aniline 
• 941-69-5 N-phenyl-maleimide 
• 75-36-5 acetyl chloride 
• 58879-90-6 3,4-dibromo-1-phenylpyrrolidine-2,5-dione 
• 902269-81-2 2,3-dibromo-N-phenyl-succinamic 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 
• 1206838-01-8 C₁₅H₁₂BrNO₂ 
• 1379867-66-9 C₁₉H₁₁F₃N₂O₂ 
• 1474012-73-1 C₁₉H₁₀F₄N₂O₂ 
• 1474012-77-5 C₂₄H₁₅FN₂O₂ 

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

Iodine-Promoted C(sp 2)-H thiolation of maleimides with dimethyl sulfoxide and thiols

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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.

Coumarin-based fluorogenic agents and uses thereof for specific protein labelling

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Reversible covalent linkage of functional molecules

The present invention relates to the use of a compound containing a moiety of formula (I) as a reagent for linking a compound of formula R1—H which comprises a first functional moiety of formula F1 to a second functional moiety of fo

A mild and selective protecting and reversed modification of thiols

One selective thiol-protecting study has been investigated for a wide range of thiols including general thiols and thiols containing multiple functional groups. The reactions of bromomaleimides and thiols under the mild condition afforded the protected products in excellent yields. The thiols can be recovered very quickly using dithiothreitol (DTT) under the mild condition.

Ring Substituent Effects on the Thiol Addition and Hydrolysis Reactions of N-Arylmaleimides

Maleimide groups are used extensively in bioconjugation reactions, but limited kinetic information is available regarding their thiol addition and hydrolysis reactions. We prepared a series of fluorogenic coumarin maleimide derivatives that differ by the

Aryloxymaleimides for cysteine modification, disulfide bridging and the dual functionalization of disulfide bonds

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A tandem [3+2] cycloaddition-elimination cascade reaction to generate pyrrolo-[3,4-c]pyrrole-1,3-diones

An efficient tandem [3+2] cycloaddition-elimination cascade sequence has been developed enabling assembly of the pharmacologically relevant pyrrolo-[3,4-c]pyrrole-1,3-dione chemotype. The strategy involves simple mixing of readily accessible oxazolin-2-on