1122-10-7

Basic information

• Product Name: 2,3-Dibromomaleinimide
• Synonyms: 3,4-dibromo-3-pyrroline-2,5-quinone;2,3-Dibromomaleimide,3,4-Dibromopyrrole-2,5-dione;1H-Pyrrole-2,5-dione, 3,4-dibroMo-;3,4-dibroMo-2,5-dihydro-1H-pyrrole-2,5-dione;2,3-Dibromomaleimide 97%;dibromo-maleimid;2,3-dibromomaleinimide;3,4-dibromo-1h-pyrrole-2,5-dione
• CAS NO: 1122-10-7
• Molecular Formula: C₄HBr₂NO₂
• Molecular Weight: 254.86
• Product Categories: API intermediates
• Mol File: 1122-10-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 228-231 °C(lit.)
• Boiling Point: 275.275 °C at 760 mmHg
• Flash Point: 120.282 °C
• Appearance: /
• Density: 2.4707 (rough estimate)
• Vapor Pressure: 0.00514mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.69±0.60(Predicted)
• CAS DataBase Reference: 2,3-Dibromomaleinimide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromomaleinimide(1122-10-7)
• EPA Substance Registry System: 2,3-Dibromomaleinimide(1122-10-7)

Safety Data

• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• RTECS: ON5100000
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 1122-10-7(Hazardous Substances Data)

Usage

Uses

2,3-Dibromomaleimide may be used in the synthesis of the following:2-bromo-3-(1H-indol-3-yl)maleimide via reaction with indolyl magnesium bromide in tetrahydrofuran2-dibromo-3-propylsulfanyl-maleimide via reaction with propanethiol and sodium acetate in methanol

General Description

2,3-Dibromomaleimide a cyclic imide, has a dipole moment of 0.30 debye based on ab initio and density functional theory (DFT) calculations.

InChI:InChI=1/C4HBr2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)

Upstream product

• 541-59-3 maleiimide 
• 54705-14-5 2,3,4,5-tetrabromopyrrole 
• 1122-12-9 2,3-dibromomaleic anhydride 
• 57-13-6 urea 
• 123-56-8 Succinimide 
• 7697-37-2 nitric acid 
• 7726-95-6 bromine 
• 32116-24-8 5-acetyl-3-nitro-1H-pyrrole 
• 393819-18-6 2-acetyl-3,4,5-tribromopyrrole 
• 1003-29-8 2-pyrrole aldehyde 
• 7732-18-5 water 
• 952009-55-1 2,5-diacetyl-3,4-dibromo-pyrrole 
• 109-97-7 pyrrole 

Downstream Products

• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 608-37-7 dibromomaleic acid 
• 7664-41-7 ammonia 
• 249763-21-1 2,5-dihydro-3,4-bis(N-phenylsulfonylindol-2-yl)-1H-pyrrole-2,5-dione 
• 569643-26-1 3-bromo-4-[2-(1-methyl-2-phenylthio-1H-imidazol-5-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 1207982-86-2 C₈₀H₁₀₅N₁₉O₂₁S₂ 
• 1334294-52-8 [Pd(N-phenylbenzaldimine(-1H))(μ-2,3-dibromomaleimidato)]2 
• 1380307-89-0 3,4-bis((4-bromophenyl)ethynyl)-1H-pyrrole-2,5-dione 
• 1380307-85-6 3,4-bis(phenylethynyl)-1H-pyrrole-2,5-dione 
• 98026-79-0 3-bromo-1H-pyrrole-2,5-dione 
• 91026-00-5 N-benzyl-2,3-dibromo-maleimide 
• 102147-52-4 N-benzyloxymethyl-3,4-dibromomaleimide 
• 40080-10-2 3,4-bis-benzylsulfanyl-pyrrole-2,5-dione 

Relevant articles and documents

A general approach to the synthesis of polyamine linked- monoindolylmaleimides, a new series of trypanothione reductase inhibitors

A simplified approach to the synthesis of 2-polyamine linked- monoindolylmaleimides has been achieved, leading to a new series of trypanothione reductase inhibitors. The conditions of access to N,2- bis(polyamine)-3-monoindolylmaleimides and N,N'-bis(monoindolylmaleimide) polyamines are described. Measured inhibitory activities towards trypanothione reductase from Tryanosoma cruzi show the importance of both aromatic moieties and polyamine chains for trypanothione reductase recognition.

Regioselective animation of 3-Bromoindolylmaleimide with amines

3-Bromoindolylmaleimide and bisindolylmaleimide were synthesized from succinimide in three steps sequnence consisting of bromination, N-methylation and indole addition in the presence of magnesium and bromoethane. They were subjeced to the regioselective amination with substituted amines to provide 3-aminoindolylmaleimides, 3- amino-N-alkylated indolylmaleimides and N-alkylated bisindolylmaleimides in good yields. The resulting indolylmaleimides represent a new class of potentially bioactive compounds.

Synthesis and cytotoxicity of novel 3-amino-4-indolylmaleimide derivatives

In an attempt to develop potent and selective antitumor agents, a series of novel 3-amino-4- indolylmaleimides were designed and synthesized. The reaction showed high regioselectivity. The structure of compound 7a was determined by an X-ray single crystal