35950-55-1

Basic information

• Product Name: 1-(5-bromofur-2-il)-2-bromo-2-nitroethene
• Synonyms: 1-(5-bromofur-2-il)-2-bromo-2-nitroethene;1-(5-BROMOFUR-2-YL)-2-BROMO-2-NITROETHENE;1(5-BROMOFUR-2-IL)-2-BROMO-2-NITROTHENE
• CAS NO: 35950-55-1
• Molecular Formula: C₆H₃Br₂NO₃
• Molecular Weight: 296.90
• Mol File: 35950-55-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 305.233 °C at 760 mmHg
• Flash Point: 138.4 °C
• Appearance: /
• Density: 2.141 g/cm³
• Vapor Pressure: 0.0015mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 1-(5-bromofur-2-il)-2-bromo-2-nitroethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-bromofur-2-il)-2-bromo-2-nitroethene(35950-55-1)
• EPA Substance Registry System: 1-(5-bromofur-2-il)-2-bromo-2-nitroethene(35950-55-1)

Safety Data

• Hazardous Substances Data: 35950-55-1(Hazardous Substances Data)

Usage

General Description

1-(5-bromofur-2-il)-2-bromo-2-nitroethene is a chemical compound that belongs to the group of organic compounds known as organobromides. These are organic compounds where bromine atom is linked to an alkyl or aryl group. This specific compound has furan ring structure where one hydrogen is replaced by a bromine atom. The bromine atom is part of the brominated furan, while the rest of compound also contains a nitro group and an ethene group. Its structure includes a double bond, representative of the ethene group, contributing to its chemical reactivity. 1-(5-bromofur-2-il)-2-bromo-2-nitroethene, like most organobromides, is likely to be used as a synthetic reagent in various chemical reactions. Its specific applications, however, will depend on the exact chemical context in question.

InChI:InChI=1/C6H3Br2NO3/c7-5(9(10)11)3-4-1-2-6(8)12-4/h1-3H/b5-3-

Synthetic route

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

Conditions	Yield
With potassium acetate In ethanol at 18 - 20℃; for 0.166667h;	68%

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

Conditions	Yield
Stage #1: 5-bromo-2-furancarboxaldehyde; bromonitromethane at 20℃; for 5h; Stage #2: With acetic anhydride In ethyl acetate at 20℃; for 1.5h;	31%

2-[(E)-2-nitroethenyl]furan (699-18-3, 32782-45-9) → (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1)

Conditions	Yield
Stage #1: 2-[(E)-2-nitroethenyl]furan With bromine In acetic acid Stage #2: With pyridine In acetic acid Further stages.;

furfural (98-01-1) → (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaOH / H2O 2.1: Br2 / acetic acid 2.2: pyridine / acetic acid View Scheme

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 3,5-dimethylphenyl boronic acid (172975-69-8) → C14H12BrNO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	93%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + phenylboronic acid (98-80-6) → C12H8BrNO3 (918429-23-9)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	90%

thiophene boronic acid (6165-68-0) + (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C10H6BrNO3S

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 8h; Suzuki reaction;	87%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + (4-ethoxyphenyl)boronic acid (22237-13-4) → C22H21NO5

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; Suzuki reaction;	87%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 3,5-dimethylphenyl boronic acid (172975-69-8) → C22H21NO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki reaction;	86%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 4-methylphenylboronic acid (5720-05-8) → C13H10BrNO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	84%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + (p-hydroxyphenyl)boronic acid (71597-85-8) → C12H8BrNO4

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	83%

morpholine (110-91-8) + (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → 4-[2-bromo-1-(5-bromofuran-2-yl)-2-nitroethyl]morpholine

Conditions	Yield
In ethanol at -8 - -5℃; for 1h;	83%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 4-methylphenylboronic acid (5720-05-8) → C20H17NO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; Suzuki reaction;	82%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8) → C15H14BrNO6

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 8h; Suzuki reaction;	77%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 1-Naphthylboronic acid (13922-41-3) → C16H10BrNO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	75%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 4-methoxyphenylboronic acid (5720-07-0) → C13H10BrNO4

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 8h; Suzuki reaction;	69%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 4-methoxyphenylboronic acid (5720-07-0) → C20H17NO5

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki reaction;	69%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + phenylboronic acid (98-80-6) → C18H13NO3

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; Suzuki reaction;	67%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + (4-ethoxyphenyl)boronic acid (22237-13-4) → 2-[(Z)-2-bromo-2-nitrovinyl]-5-(4-ethoxyphenyl)furan

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 8h; Suzuki reaction;	67%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) + 2-Methoxyphenylboronic acid (5720-06-9) → C20H17NO5

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki reaction;	64%

thiophene boronic acid (6165-68-0) + (Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C14H9NO3S2

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki reaction;	42%

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C22H15NO3

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 8 h / 90 °C 2: 63 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 90 °C View Scheme

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C20H17NO3

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 8 h / 90 °C 2: 74 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 90 °C View Scheme

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C19H15NO3

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 8 h / 90 °C 2: 79 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 90 °C View Scheme

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C19H15NO4

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 8 h / 90 °C 2: 75 percent / K3PO4 / Pd(PPh3)4 / dioxane; H2O / 90 °C View Scheme

(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene (35950-55-1) → C16H11NO3S

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 8 h / 90 °C 2: 57 percent / K3PO4 / Pd(PPh3)4 / toluene; H2O / 90 °C View Scheme

Upstream product

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 563-70-2 bromonitromethane 
• 699-18-3 2-[(E)-2-nitroethenyl]furan 
• 98-01-1 furfural 

Downstream Products

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 563-70-2 bromonitromethane 
• 918429-23-9 C₁₂H₈BrNO₃ 

Relevant articles and documents

Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity

A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 μg/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile.

Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2-nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized β-substituted gem-bromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gem-bromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, 1H, and 13C-{1H} NMR, including 1H-13C HMQC and HMBC).