3-Bromo-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 3-Bromo-1H-pyrrole-2,5-dione
• CAS No.: 98026-79-0
• Molecular Formula: C4H2BrNO2
• Molecular Weight: 175.969
• Hs Code.: 2925290090
• European Community (EC) Number: 834-871-0
• ChEMBL ID: CHEMBL484256
• Metabolomics Workbench ID: 138332
• Nikkaji Number: J1.522.732J
• Mol file: 98026-79-0.mol

Synonyms:3-Bromo-1H-pyrrole-2,5-dione;98026-79-0;3-bromo-2,5-dihydro-1H-pyrrole-2,5-dione;3-bromomaleimide;2-Bromomaleimide;3-bromopyrrole-2,5-dione;bromomaleimide;1H-Pyrrole-2,5-dione, 3-bromo-;MFCD09035063;SCHEMBL589316;AMY458;CHEMBL484256;LCZC2688;QBLRHWLVSHLMSP-UHFFFAOYSA-N;YDA02679;AC8268;AKOS004122987;SB63898;CS-10874;SY264831;CS-0112984;EN300-65098;Z1258992610

Chemical Property of 3-Bromo-1H-pyrrole-2,5-dione

Chemical Property:

• Melting Point: 153-154 °C
• Boiling Point: 267.6±33.0 °C(Predicted)
• PKA: 6.61±0.40(Predicted)
• PSA: 49.66000
• Density: 2?+-.0.06 g/cm3(Predicted)
• LogP: 0.19750
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 174.92689
• Heavy Atom Count: 8
• Complexity: 185

Purity/Quality:

99%+, ^*data from raw suppliers

2-Bromomaleimide 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC1=O)Br

Technology Process of 3-Bromo-1H-pyrrole-2,5-dione

There total 10 articles about 3-Bromo-1H-pyrrole-2,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,3-dibromomaleimide (1122-10-7) → 3-bromo-1H-pyrrole-2,5-dione (98026-79-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2016.05.027

Reference yield: 88.0%

maleiimide (541-59-3,25721-74-8) → 3-bromo-1H-pyrrole-2,5-dione (98026-79-0)

Guidance literature:

maleiimide; With bromine; In dichloromethane; for 1h; Reflux;

With triethylamine; In tetrahydrofuran; at 20 ℃; Cooling with ice;

DOI:10.1002/cjoc.201900146

Reference yield: 86.0%

(3R*, 4R*)-3,4-dibromopyrrolidine-2,5-dione (33685-65-3) → 3-bromo-1H-pyrrole-2,5-dione (98026-79-0)

Guidance literature:

With sodium acetate; In acetic acid; for 1.5h; Reflux; Inert atmosphere;

DOI:10.1039/c4cc02107j

upstream raw materials:

maleiimide

Succinimide

(3R*, 4R*)-3,4-dibromopyrrolidine-2,5-dione

1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone

Downstream raw materials:

Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys

C₈₅H₁₁₀N₂₀O₂₃S₂

3-phenoxypyrrole-2,5-dione

3-(phenylthio)maleimide

Refernces

• 1、 Tedaldi, Lauren M.,Smith, Mark E. B.,Nathani, Ramiz I.,Baker, James R.. "Bromomaleimides: New reagents for the selective and reversible modification of cysteine". . p. 6583 - 6585. Retrieved 2009.
• 2、 -. "Cheap and efficient preparation method of benzene triimide and derivative thereof". Paragraph 0052; 0059; 0060. . Retrieved 2020/05/01.
• 3、 Tuo, De-Hui,He, Qing,Wang, Qi-Qiang,Ao, Yu-Fei,Wang, De-Xian. "Benzene Triimides: Facile Synthesis and Self-Assembly Study". supporting information. p. 684 - 688. Retrieved 2019/05/28.