1-(5-Bromofur-2-il)-2-bromo-2-nitroethene

Base Information

• Chemical Name: 1-(5-Bromofur-2-il)-2-bromo-2-nitroethene
• CAS No.: 35950-55-1
• Molecular Formula: C6H3Br2NO3
• Molecular Weight: 296.903
• Hs Code.: 2932190090
• ChEMBL ID: CHEMBL4749548
• Mol file: 35950-55-1.mol

Synonyms:1-(5-bromofur-2-il)-2-bromo-2-nitroethene;1-5-BNF

Chemical Property of 1-(5-Bromofur-2-il)-2-bromo-2-nitroethene

Chemical Property:

• Vapor Pressure: 0.0015mmHg at 25°C
• Refractive Index: 1.658
• Boiling Point: 305.233 °C at 760 mmHg
• Flash Point: 138.4 °C
• PSA: 58.96000
• Density: 2.141 g/cm³
• LogP: 3.53530
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 296.84592
• Heavy Atom Count: 12
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

1-(5-BROMOFUR-2-IL)-2-BROMO-2-NITROETHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC(=C1)Br)C=C([N+](=O)[O-])Br
• Isomeric SMILES: C1=C(OC(=C1)Br)/C=C(\[N+](=O)[O-])/Br
• General Description: 1-(5-Bromofur-2-yl)-2-bromo-2-nitroethene is a dibromo-substituted nitrovinylfuran compound exhibiting broad-spectrum antibacterial activity, including efficacy against multidrug-resistant strains like MRSA. It acts as a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis, through irreversible covalent binding to cysteine residues, forming adducts with thiol groups and inducing disulfide bonds. 1-(5-bromofur-2-il)-2-bromo-2-nitroethene and its degradation products maintain strong antibacterial potency (MIC < 4 μg/mL) but require optimization to improve selectivity and reduce cytotoxicity for clinical development. Additionally, it serves as a versatile synthetic intermediate in regioselective coupling reactions, such as Suzuki cross-coupling, enabling further functionalization of the furan and alkenyl moieties.

Technology Process of 1-(5-Bromofur-2-il)-2-bromo-2-nitroethene

There total 6 articles about 1-(5-Bromofur-2-il)-2-bromo-2-nitroethene 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: 68.0%

β-<5-Brom-furyl-2>-α,β-dibrom-nitro-ethylen → (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1)

Guidance literature:

With potassium acetate; In ethanol; at 18 - 20 ℃; for 0.166667h;

DOI:10.1134/S1070363215060110

Reference yield: 35.0%

5-bromo-2-furancarboxaldehyde (1899-24-7) + bromonitromethane (563-70-2) → 1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1)

Guidance literature:

With ammonium acetate; In toluene; for 4h; Reflux; Dean-Stark;

DOI:10.1016/j.bmc.2012.11.018

Reference yield: 31.0%

5-bromo-2-furancarboxaldehyde (1899-24-7) + bromonitromethane (563-70-2) → (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1)

Guidance literature:

5-bromo-2-furancarboxaldehyde; bromonitromethane; at 20 ℃; for 5h;

With acetic anhydride; In ethyl acetate; at 20 ℃; for 1.5h;

DOI:10.1055/s-0032-1317695

upstream raw materials:

5-bromo-2-furancarboxaldehyde

bromonitromethane

2-[(E)-2-nitroethenyl]furan

furfural

Downstream raw materials:

5-bromo-2-furancarboxaldehyde

bromonitromethane

C₁₂H₈BrNO₃