85553-51-1

Basic information

• Product Name: 2-(3-BROMOPHENYL)FURAN
• Synonyms: 2-(3-BROMOPHENYL)FURAN;3-BROMO-(2-FURYL)BENZENE;2-(3-Bromophenyl)furan 97%
• CAS NO: 85553-51-1
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.07
• Mol File: 85553-51-1.mol

Chemical Properties

• Boiling Point: 266.829 °C at 760 mmHg
• Flash Point: 115.174 °C
• Appearance: /
• Density: 1.451 g/cm³
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 2-(3-BROMOPHENYL)FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-BROMOPHENYL)FURAN(85553-51-1)
• EPA Substance Registry System: 2-(3-BROMOPHENYL)FURAN(85553-51-1)

Safety Data

• Hazardous Substances Data: 85553-51-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(3-Bromophenyl)furan is utilized as a key intermediate in organic synthesis for the creation of a variety of complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(3-Bromophenyl)furan is employed as a structural element in the design and synthesis of new drug candidates. Its presence in a molecule can influence pharmacokinetic and pharmacodynamic properties, potentially leading to the development of more effective and safer medications.
Used in Pharmaceutical Development:
2-(3-Bromophenyl)furan is used as a building block in the development of pharmaceuticals, where its specific structural features may contribute to the biological activity of the resulting compounds. It may be incorporated into drug molecules to enhance their therapeutic effects or to improve their delivery to target sites within the body.
Used in Agrochemicals:
In agrochemical applications, 2-(3-Bromophenyl)furan may be used as a component in the synthesis of new pesticides, herbicides, or other crop protection agents. Its chemical properties could be harnessed to create molecules with improved efficacy, selectivity, and environmental compatibility.
Used in Materials Science:
2-(3-Bromophenyl)furan also finds use in materials science, where it may be incorporated into the development of new materials with specific properties. Its unique structure could contribute to the creation of materials with tailored characteristics for use in various industries, such as electronics, coatings, or advanced composites.

InChI:InChI=1/C10H7BrO/c11-9-4-1-3-8(7-9)10-5-2-6-12-10/h1-7H

Upstream product

• 196953-06-7 1-(3-bromophenyl)-2,3-butadien-1-one 
• 110-00-9 furan 
• 27246-81-7 3-bromophenylhydrazine hydrochloride 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 591-19-5 m-Bromoaniline 
• 110-46-3 isopentyl nitrite 
• 591-18-4 1-Bromo-3-iodobenzene 
• 118486-94-5 2-(tributylstannyl)furan 
• 3132-99-8 m-bromobenzoic aldehyde 

Downstream Products

• 85553-52-2 3-(furan-2-yl)benzaldehyde 
• 946647-05-8 C₄₉H₇₈N₂O₁₃ 
• 946647-06-9 C₄₉H₇₆N₂O₁₃ 
• 946647-07-0 C₄₉H₈₀N₂O₁₃ 

Relevant articles and documents

Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes

Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.

Visible-Light-Promoted Arylation Reactions Photocatalyzed by Bismuth(III) Oxide

Bismuth(III) oxide has been successfully applied as a photocatalyst in the arylation of heteroarenes with diazonium salts. With a low catalyst loading (1 to 5 mol-%), this cheap and nontoxic semiconductor could efficiently promote the formation of the aryl radical under visible light irradiation. The arylated products are obtained in moderate to good yields, and the process admits straightforward scale-up (10 mmol; 1 mol-% Bi2O3). In two cases, the diazonium salt was generated in situ and used in the photocatalytic arylation in a tandem manner. Besides heteroarenes, Bi2O3 also catalyzed the arylation of differently substituted alkenes and alkynes, thus representing a viable and practical alternative to the more commonly used ruthenium complexes and organic dyes.

Porphyrin-Catalyzed Photochemical C–H Arylation of Heteroarenes

Organic dyes are a promising class of photoredox catalysts and offer a meaningful alternative to broadly applied Ru and Ir complexes. We found that porphyrins with tuned physicochemical properties, by tailoring various substituents at the periphery of the

Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters

Stille cross coupling protocols were utilized for the synthesis of 3-(biaryl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters, which furnished products in high yields where in some cases Suzuki coupling under the conditions utilized provided complex reaction mixture. Samarium iodide reduction of the resulting coupling products produced both of the 2β-carbomethoxy-3- biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2α-carbomethoxy-3- biaryl-8-oxabicyclo[3.2.1]octane diastereomers. Among the series synthesized, the benzothiophene substituted compounds demonstrated significant binding profiles of inhibition of WIN 35,438 with 177-fold selectivity for DAT versus SERT.

Gold(III) porphyrin-catalyzed cycloisomerization of allenones

Gold(III) porphyrin-catalyzed cycloisomerization of allenones gave the corresponding furans in good to excellent yields (up to 98%) and with quantitative substrate conversions. By recovering the Au(III) catalyst, a recyclable catalytic system is developed with over 8300 product turnovers attained for the cycloisomerization of 1-phenyl-buta-2,3-dien-1-one. The versatility of the gold(III) porphyrin catalyst was exemplified by its application to the hydroamination and hydration of phenylacetylene in 73% and 87% yield, respectively.

Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls

The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields

Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: A novel method for hetero biaryl coupling

A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.

C-C-Bond Formation by the Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones: Selectivity and Mechanistic Aspects

The scope of the palladium-catalyzed cyclization/dimerization of terminal allenyl ketones 1 to the 2,4-disubstituted furans 3 has been investigated. Simplified and improved conditions almost exclusively provided the dimer 3, accompanied by only traces of the easily separable monomer 2. The formation of an isomer of 3, the unconjugated ketone 4, was completeley suppressed. Under these mild conditions, besides the normal functional group tolerance known for palladium-catalyzed reactions, an interesting selectivity was observed with functional groups that are known to react either in palladium-catalyzed reactions or reactions catalyzed by other transition-metals. Thus aryl halides, terminal alkynes, 1,6-enynes, and α-allenic alcohols were tolerated. In the latter example the selective reaction of only one out of two different allenes was achieved. Mechanistic investigation indicated a Pd(II)/Pd(IV)-cycle involving palladium(II)-γ-alkoxyvinylcarbene and furylpalladium(IV) hydride intermediates, although a second pathway for the formation of the dimer 3 which also involves Pd(IV)-intermediates like the 3,4-dimethylenepalladacyclopentane 23 and the 3-methylenepalladacyclobutane-like structure 15 (respectively 25) could not completely be excluded.

Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates

Disclosed and exemplified are insecticidal and acaricidal optionally substituted furylbenzyl, thienylbenzyl, pyrazinylbenzyl, or pyridinzylbenzyl esters of the pyrethroid acids, novel pyrethroid alcohols and other intermediates, and compositions, a method of use and a process for preparation of the esters.