3,4-Dibromo-1h-pyrrole-2,5-dione

Base Information

• Chemical Name: 3,4-Dibromo-1h-pyrrole-2,5-dione
• CAS No.: 1122-10-7
• Molecular Formula: C4HBr2NO2
• Molecular Weight: 254.865
• Hs Code.: 2925190090
• European Community (EC) Number: 628-162-3
• UNII: 8CQ5P92W3E
• DSSTox Substance ID: DTXSID40149942
• Nikkaji Number: J171.279I
• Wikidata: Q72464487
• Metabolomics Workbench ID: 100731
• ChEMBL ID: CHEMBL447173
• Mol file: 1122-10-7.mol

Synonyms:2,3-dibromomaleimide

Chemical Property of 3,4-Dibromo-1h-pyrrole-2,5-dione

Chemical Property:

• Appearance/Colour: Off white flakes, Chips, Powder
• Vapor Pressure: 0.00514mmHg at 25°C
• Melting Point: 228-231 °C(lit.)
• Refractive Index: 1.705
• Boiling Point: 275.275 °C at 760 mmHg
• PKA: 4.69±0.60(Predicted)
• Flash Point: 120.282 °C
• PSA: 46.17000
• Density: 2.662 g/cm₃
• LogP: 0.97300
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.83535
• Heavy Atom Count: 9
• Complexity: 199

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4-Dibromo-1-H-pyrrole-2,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3,4-Dibromo-1h-pyrrole-2,5-dione

There total 25 articles about 3,4-Dibromo-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: 60.0%

2,3-dibromomaleic anhydride (1122-12-9) → 2,3-dibromomaleimide (1122-10-7)

Guidance literature:

With ammonium acetate; acetic acid; for 16h; Heating;

DOI:10.1016/j.tet.2005.03.016

Reference yield: 53.0%

maleiimide (541-59-3,25721-74-8) → 2,3-dibromomaleimide (1122-10-7)

Guidance literature:

With bromine; at 140 - 160 ℃; for 8.5h;

DOI:10.1002/ejoc.201201525

Reference yield: 41.0%

Succinimide (123-56-8,89963-74-6) → 2,3-dibromomaleimide (1122-10-7)

Guidance literature:

With bromine; at 160 ℃;

DOI:10.1248/cpb.46.707

upstream raw materials:

maleiimide

pyrrole

2,3,4,5-tetrabromopyrrole

2,3-dibromomaleic anhydride

Downstream raw materials:

N-benzyloxymethyl-3,4-dibromomaleimide

3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione

N-benzyl-2,3-dibromo-maleimide

2,5-dihydro-3,4-bis(N-phenylsulfonylindol-2-yl)-1H-pyrrole-2,5-dione

Refernces

• 1、 Li, Xiangmin,Li, Hongxian,Yang, Wei,Zhuang, Jinchen,Li, Hao,Wang, Wei. "A mild and selective protecting and reversed modification of thiols". . p. 2660 - 2663. Retrieved 2016.
• 2、 Brenet, Simon,Baptiste, Benoit,Philouze, Christian,Berthiol, Florian,Einhorn, Jacques. "BINOL-fused maleimides - A new class of C2-symmetric chiral imides". supporting information. p. 1041 - 1045. Retrieved 2013/04/23.