23145-07-5

Basic information

• Product Name: 5-Bromo-1-benzofuran
• Synonyms: 5-BROMO-1-BENZOFURAN;5-BROMOBENZO[BETA]FURAN;5-BROMOBENZOFURAN;BUTTPARK 95\50-66;5-Bromobenzo[b]furan;5-Bromobenzo[beta]furan, 98 %;5-Bromobenzofuran ,97%;Benzofuran, 5-broMo-
• CAS NO: 23145-07-5
• Molecular Formula: C₈H₅BrO
• Molecular Weight: 197.03
• Product Categories: pharmacetical
• Mol File: 23145-07-5.mol

Chemical Properties

• Melting Point: 8°C(lit.)
• Boiling Point: 226°C(lit.)
• Flash Point: 95.2 °C
• Appearance: Colorless to pale yellow liquid
• Density: 1.573 g/mL at 25 °C
• Vapor Pressure: 0.0835mmHg at 25°C
• Refractive Index: n20/D1.605
• Storage Temp.: Refrigerated.
• CAS DataBase Reference: 5-Bromo-1-benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-benzofuran(23145-07-5)
• EPA Substance Registry System: 5-Bromo-1-benzofuran(23145-07-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 23145-07-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1-benzofuran is used as a key intermediate in the synthesis of 1-(7-benzofuranyl)-4-methylpiperazine, a compound that exhibits strong and selective binding to the serotonin receptor 5-HT2A, even in the presence of the receptor 5-HT7. This selective binding property makes it a promising candidate for the development of drugs targeting serotonin-related disorders.
Used in Chemical Synthesis:
As a light yellow liquid with specific chemical properties, 5-Bromo-1-benzofuran can be utilized in the synthesis of various other organic compounds, contributing to the advancement of chemical research and the development of new materials and pharmaceuticals.

InChI:InChI=1/C8H5BrO/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5H

Upstream product

• 79-11-8 chloroacetic acid 
• 1761-61-1 5-bromosalicyclaldehyde 
• 66826-78-6 5-bromo-2,3-dihydrobenzo[b]furan 
• 271-89-6 1-benzofurane 
• 13997-74-5 2-allyl-4-bromophenol 
• 24589-89-7 2-(4-bromo-2-formylphenoxy)acetic acid 
• 108-24-7 acetic anhydride 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 106-41-2 4-bromo-phenol 
• 591-20-8 3-Bromophenol 
• 204452-94-8 2-(3-bromophenoxy)acetaldehyde diethyl acetal 
• 104743-20-6 2-allyl-1-allyloxy-4-bromobenzene 
• 61131-72-4 trans-4-bromo-2-(2-nitrovinyl)phenol 
• 96853-37-1 4-Bromo-2-(2-nitro-ethyl)-phenol 

Downstream Products

• 10035-16-2 benzofuran-5-carbaldehyde 
• 41744-27-8 eupomatenoid-3 
• 41744-26-7 eupomatenoid 6 
• 40341-58-0 (E)-2-(4-methoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 
• 41744-28-9 eupomatenoid-5 
• 41744-29-0 (E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 
• 365448-06-2 5-bromo-2-(4-methoxyphenyl)-3-methylbenzo[b]furan 
• 365448-05-1 3,5-dibromo-2-(4-methoxyphenyl)benzo[b]furan 
• 365448-15-3 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)phenoxy]dimethylsilane 
• 489422-89-1 3,5-dibromo-2-(3,4-dimethoxyphenyl)benzo[b]furan 
• 489423-03-2 (E)-tert-butyldimethyl{4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}silane 
• 489423-02-1 (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane 
• 489422-91-5 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)-2-methoxyphenoxy]dimethylsilane 

Relevant articles and documents

Substitution vs. addition. Regioselective electro-bromination of benzofuran

Regioselective electro-bromination of benzofuran (2) was achieved successfully by an adequate choice of solvents and bromide salts to afford 5-bromobenzofuran (1), 5,7-dibromobenzofuran (3), and 2,3-dibromo-2,3-dihydrobenzofuran (4), respectively. Upon electrolysis of benzofuran (2) in AcOH/H2O (100/1) containing NH4Br, substitution at the C(5)-position of benzofuran (2) proceeded smoothly to afford 5-bromobenzofuran (1). After passage of totally 4 F/mol of electricity in a similar medium, 5,7-dibromobenzofuran (3) was obtained as a sole product. On the other hand, electrolysis of benzofuran (2) in CH2Cl2/H2O (1/1) and/or AcOH/H2O (10/1) in the presence of either NaBr or NH4Br afforded 2,3-dibromo-2,3-dihydrobenzofuran (4), exclusively.

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

REACTIVE MESOGEN, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY COMPRISING THE SAME

The invention relates to a reactive mesogen, a liquid crystal composition and a liquid crystal display comprising the same. The reactive mesogen is represented by a chemical formula 1, wherein, X1 andX2 independently are hydrogen or halogen, Y is -O-, -S-

Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C?H Activation with Silyldimesitylborane

Direct dimesitylborylation of benzofuran derivatives by a C?H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph2MeSi-BMes2 afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor–(π-spacer)–acceptor systems with intriguing solvatochromic luminescence properties.

Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles

A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.

PYRAZOLE DERIVATIVES AS MALT1 INHIBITORS

Disclosed are compounds, compositions and methods for treating of diseases, syndromes, conditions, and disorders that are affected by the modulation of MALT1. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, R5, R6, R5, G1, and G2 are defined herein.

Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines

A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.

5-bromo-benzofuran preparation method

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 5-bromobenzofuran. The preparation method of 5-bromobenzofuran comprises the following steps: p-bromophenol and 2-bromoacetaldehyde dimethyl aceta

Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate

Visible light-induced monofluoromethylenation of benzofurans and benzothiophenes with ethyl bromofluoroacetate was developed. This method provided a convenient access to novel α-fluoro-α-heteroarylesters under mild reaction conditions.

Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals

An efficient and environmentally benign heterogeneous catalytic process for the synthesis of 2,3-unsubstituted benzo[b]furans has been established via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals. By utilizing tin-exchanged H-β zeolite (Sn-β) as catalyst, a wide range of functionalized 2,3-unsubstituted benzo[b]furans could be prepared in good to excellent yields. The Sn-β zeolite catalyst also exhibited excellent shape selectivity on the cyclization of meta-substituted 2-aryloxyacetaldehyde acetals, and 6-substituted isomers were preferably formed up to 97% regio-selectivity. Moreover, Sn-β zeolite could be easily recovered and reused without any noticeable activity loss.