31555-60-9

Usage

Uses

Used in Pharmaceutical Industry:
5-bromothiophene-2-carbonyl chloride is used as a building block for the synthesis of pharmaceuticals for its ability to easily react with nucleophiles and serve as a key intermediate in various chemical reactions.
Used in Agrochemical Industry:
5-bromothiophene-2-carbonyl chloride is used as a building block for the synthesis of agrochemicals for its ability to easily react with nucleophiles and serve as a key intermediate in various chemical reactions.
Used in Organic Chemistry Research:
5-bromothiophene-2-carbonyl chloride is used as a valuable tool for organic chemists in the production of complex molecules due to its reactivity as an acyl chloride and its role as a key intermediate in various chemical reactions.
Used in Industrial Applications:
5-bromothiophene-2-carbonyl chloride is used in industrial applications for the synthesis of various organic compounds, taking advantage of its reactivity and its function as a key intermediate in chemical reactions.

Upstream product

• 7311-63-9 5-bromothiophene-2-carboxylic acid 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 527-72-0 2-thiophenylcarboxylic acid 
• 5370-25-2 2-Acetyl-5-bromothiophene 
• 5751-83-7 ethyl 5-bromothiophene-2-carboxylate 

Downstream Products

• 5751-83-7 ethyl 5-bromothiophene-2-carboxylate 
• 859489-42-2 N,N'-bis-(5-bromo-thiophene-2-carbonyl)-o-phenylenediamine 
• 76371-66-9 5-bromo-2-thiophene carboxamide 
• 83851-78-9 (5-bromo-2-thenoyl)-DL-Phe-OMe 
• 83851-79-0 (5-bromo-2-thenoyl)-L-Tyr-OMe 
• 98215-45-3 5-Bromo-thiophene-2-carboxylic acid [2-(3,4-dimethoxy-phenyl)-ethyl]-amide 
• 62224-19-5 5-bromo-2-thiophenecarboxylic acid methyl ester 
• 98027-27-1 5-bromo-thiophene-2-carboxylic acid hydrazide 
• 867006-38-0 5-bromothiophene-2-carboxylic acid 3,5-difluorobenzylamide 
• 890082-24-3 2-bromo-thiophene-5-carboxylic acid (1S,2S)-2-(benzyloxycyclopent-1-yl)amide 
• 1113048-37-5 C₂₁H₁₈BrNO₄S 

Relevant academic research and scientific papers

Quater-, quinque-, and sexithiophene organogelators: Unique thermochromism and heating-free sol-gel phase transition

A series of quater-, quinque-, and sexithiophene derivatives bearing two cholesteryl groups at the α-position, which are abbreviated as 4T-(chol)2, 5T-(chol)2, and 6T-(chol)2, respectively, have been synthesized. It has been found that these oligothiophene derivatives act as excellent organogelators for various organic fluids and show the unique thermochromic behaviors through the sol-gel phase transition. It was shown on the basis of extensive investigations, performed with UV-visible spectroscopy, circular dichroism (CD), transmission electron" microscopy (TEM), scanning electron microscopy (SEM), and atomic force microscopy (AFM), that these gelators self-assemble into the one-dimensional structures in the organogels, in which the π-block moieties of the oligothiophenes are stacked in an H-aggregation mode. Surprisingly, an AFM image shows that 4T-(chol) 2 forms unimolecular fibers in a left-handed helical sense, whereby one pitch of the helical fiber is constructed by 400-540 4T-(chol)2, molecules. Very interestingly, the conformational change in the oligothiophene moieties can be visually detected: for example, 6T-(chol)2 shows a specific absorption maximum in the gel (λmax = 389 nm) and in the solution (λmax = 439 nm). In addition, a sol-gel phase transition of the 6T-(chol)2 gel was implemented by addition of oxidizing and reducing reagents such as FeCl3 and ascorbic acid, respectively. The stimuli-responsive functionality of the oligothiophene-based organogels makes them promising candidates for switchable opto- and electronic soft materials.

Non-covalent bridging of bithiophenes through chalcogen bonding grips

In this work, chalcogen functionalized dithiophenes, equipped on both extremities with chalcogen-bonding recognition heterocycles, have been prepared following two synthetic pathways. The insertion of the chalcogenazolo[5,4-β]pyridine allows the control of the organization at the solid state. X-Ray diffraction analysis of the single crystals, showed that the Te-doped derivatives give the most persistant assemblies, with the molecules arranging at solid-state in wire-like polymeric structures through Te?N interactions. As expected, the introduction of the Se and Te atoms, dramatically decreases the emission properties, with the Te-bearing congeners being virtually non emissive.

D–π–A–π–D type solvatochromic fluorescence probes based on triphenylamine: Synthesis, photophysical properties and application

Two D–π–A–π–D type solvatochromic fluorescence probes (JT1 and JT2) based on triphenylamine have been synthesized. The photophysical and electrochemical properties of these probes as well as their solvatochromic behavior were studied. The Stokes shifts of JT1 and JT2 reach 175 nm (6417.0 cm?1) and 218.6 nm (9916.7 cm?1) in the acetonitrile solution, respectively. There is an excellent linear correlation between the Stokes shifts and the ET (30) solvent polarity values in different solvents. The high responsiveness of JT1 and JT2 to solvent polarity makes them promising candidates for solvatochromic fluorescence probes, especially for the detection of the polarity of non-proton solvents or the content of water in tetrahydrofuran.

Solution-processable n-type organic field-effect transistor (OFET) materials based on carbonyl-bridged bithiazole and dioxocyclopentene-annelated thiophenes

A series of electronegative π-conjugated compounds composed of carbonyl-bridged bithiazole and alkyl-substituted dioxocyclopenta[b]thiophene were synthesized as a candidate for solution-processable n-type organic semiconductor materials and characterized on the basis of photophysical and electrochemical properties. Cyclic voltammetry measurements showed that the first half-wave reduction potentials of these compounds are between -0.97 and -1.14 V versus ferrocene/ferrocenium, which corresponds to lowest unoccupied molecular orbital energy levels between -3.83 and -3.66 eV. Thanks to hexyl or dodecyl groups in the molecules, the compounds are sufficiently soluble to realize the fabrication of their thin films through a spin-coating method. As a result, the prepared organic field-effect transistors based on these newly developed compounds exhibited n-channel characteristics not only under vacuum but also in air, and the best field-effect electron mobility observed under vacuum was 0.011 cm2 V-1 s-1 with an on/off ratio of 108 and a threshold voltage of 16 V. Copyright

Host-guest co-assembly triggered turn-on and ratiometric sensing of berberine and its detoxicating

Fluorescent sensing for specific detection of berberine is an important issue in view of its potential jeopardization to food safety and human health, but remains less investigated. To the best of our knowledge, there is no fluorescence turn-on and ratiometric sensors available for specific detection of berberine. In this study, calix[4]carbazole (3) has been synthesized and its property of recognizing berberine has been evaluated by UV–vis, fluorescence, NMR, DLS and TEM techniques. The results show that 3 selectively recognizes berberine among the tested drugs and detects it with turn-on and ratiometric fluorescence due to their co-assembly nature. Moreover, 3 is not only low toxic and can reduce toxicity of berberine to human normal liver L02 cell, but also can release berberine to tumor HepG2 cells at acid micro-environment. It therefore holds a great potential for further exploration

Fine tuning of the photovoltaic properties of triarylethylene-bridged dyes by altering the position and proportion of phenyl/thienyl groups

Four triarylethylene (TAE) π-spacers have been applied for Y-shaped dyes in dye-sensitized solar cells (DSSCs) and their effects on photovoltaic performance have been fully investigated. All photosensitizers inherit the ability of three-dimensional TAE to weaken the π-π stacking in aggregation state, while their suppression on charge recombination in electrolytes presents a high reliance on the position and proportion of phenyl/thienyl groups embedded in TAE moieties. In iodine electrolytes, benzene-rich triphenylethene-based dye JY65 achieves the best open-circuit voltage of 739 mV, sharply higher than that of 614 mV for trithienylethene (TTE)-based dye JY63. Moreover, dyes JY64 and D-1 with hetero-TAE-bridge tend to show better power convention efficiency (PCE) stemming from the higher short-circuit current density and moderate open-circuit voltage. Whereas in cobalt electrolytes, the TTE-bridged JY63 attains a superior PCE of 5.84%, inversely surpassing the value of 5.28% based on D-1 under the same condition. Therefore, tuning the TAE skeletons via altering the position and proportion of aryl groups in it would bring in a promising design for anti-stacking sensitizers to meet the varied demand in DSSCs.

PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS

Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Discovery and structural optimization of 9-O-phenylsulfonyl-berberines as new lipid-lowering agents

Berberine is a quaternary isoquinoline alkaloid that exhibits potent hypoglycemic and hypolipidemic activity. Many medicinal chemists are currently working on structural modifications around the parent scaffold of berberine, expecting to further enhance its hypolipidemic activity and reducing its cytotoxicity. In this study, a focused berberine-like compound library containing 12,600 molecules was built via the introduction of various “drug-like” fragments at the C8 and C9 positions of berberine. Sixteen comopounds were hit by using the in-house QSAR models previously reported by our group. Considering synthesis feasibility and the cost of building-blocks, only four berberine analogs (library ID: 2028, 3847, 6033, and 12456) were selected and synthesized for investigating their lipid-lowering activities. Preliminary lipid-lowering study showed that compound 12456 with the phenylsulfonyl group at the C9 position had potent cholesterol inhibitory activity in HepG2 cells, superior to that of the parent compound berberine. Subsequently, a total of twenty-five 9-O-phenylsulfonyl-berberines (1a-1y) and twenty-four 9-O-phenylsulfonyl-tetrahydroberberine (2a-2x) were designed, synthesized, and evaluated by lipid-lowering experiments. The results displayed that most compounds exhibited more lipid-lowering activities than berberine. Among them, compound 1m inhibited cholesterol production close to 50% in both cell models when compared with the blank control; the inhibition of triglycerides exceeded 70%. Moreover, 1m also had significant pharmacological effects on the inhibition of LDLC and promotion of HDLC production, especially in the HepG2 cell model, in which the inhibitory rate against LDLC was close to 70% and the increase rate of HDLC was more than 75%. The hypolipidemic experiment of SD rats demonstrated that after 40 days of administration (1m, 15 mg/kg/d), blood cholesterol was reduced by 19.6%, triglycerides reduced by 34.52%, and LDLC reduced by 41.49%, when compared with the high-fat diet model (HFD). In addition, after 80 days of administration, the three indexes of 1m were still better than that of berberine. Oil Red O staining and H&E staining results showed that 1m exhibited potent lipid scavenging activity. All in all, 1m was discovered and identified as a potent lipid-lowering agent and a new berberine-like candidate, being evaluated by subsequent studies.

Thiophene 2, 5-disubstituted-tetrahydroisoquinoline compound and preparation and application thereof

The invention discloses a thiophene 2, 5-disubstituted tetrahydroisoquinoline compound as shown in a formula (I), a preparation method thereof and application thereof as a tumor multidrug resistance reversal agent. Pharmacological experiment results show that the compound provided by the invention has excellent tumor multidrug resistance reversal activity and sensitization chemotherapy drug activity, and can be clinically used as a malignant tumor multidrug resistance reversal agent and a chemotherapy drug sensitizer.

Pine Rosin as a Valuable Natural Resource in the Synthesis of Fungicide Candidates for Controlling Fusarium oxysporum on Cucumber

To improve the effect of pine rosin in plant fungicides, four series of dehydroabietyl-1,3,4-thiadiazole derivatives from the natural product rosin were synthesized. Based on the evaluation of the in vitro antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oxysporum, and Magnaporthe oryzae, rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound 3e [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against F. oxysporum with an EC50 of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The in vivo antifungal activity results showed that 3e exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound 3e on F. oxysporum was it changed the mycelial morphology, increased the cell membrane permeability, and inhibited the synthesis of ergosterol in the mycelia. Furthermore, the quantitative structure-activity relationship studies revealed that the frontier orbital energy in the molecule had a key role in the antifungal activity through the conjugation and electrostatic interaction between compound 3e and the receptors of the target. Thus, the present study highlighted the application of rosin-based fungicidal candidates and exploited efficient plant pesticides for sustainable crop production.