415718-60-4

Basic information

• Product Name: 4-(5-BROMOTHIOPHEN-2-YL)BENZONITRILE
• Synonyms: 4-(5-BROMOTHIOPHEN-2-YL)BENZONITRILE
• CAS NO: 415718-60-4
• Molecular Formula: C₁₁H₆BrNS
• Molecular Weight: 264.14
• Product Categories: pharmacetical
• Mol File: 415718-60-4.mol

Chemical Properties

• Boiling Point: 360.7°Cat760mmHg
• Flash Point: 171.9°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-(5-BROMOTHIOPHEN-2-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-BROMOTHIOPHEN-2-YL)BENZONITRILE(415718-60-4)
• EPA Substance Registry System: 4-(5-BROMOTHIOPHEN-2-YL)BENZONITRILE(415718-60-4)

Safety Data

• Hazardous Substances Data: 415718-60-4(Hazardous Substances Data)

Usage

Uses

4-(5-Bromothiophen-2-yl)benzonitrile can be prepared to use as antiprotozoals.

InChI:InChI=1/C11H6BrNS/c12-11-6-5-10(14-11)9-3-1-8(7-13)2-4-9/h1-6H

Upstream product

• 15961-46-3 4-(2-thienyl)benzonitrile 
• 1003-09-4 2-bromothiophene 
• 3058-39-7 4-iodobenzonitrile 
• 29504-81-2 5-iodo-2-bromothiophene 
• 126747-14-6 4-cyanophenylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 

Relevant articles and documents

Compound and application thereof

The compound has the structure shown in the formula (1), X is O or S, and L is selected from a single bond. A substituted or unsubstituted C5 - C60 arylene group, a substituted or unsubstituted C3 - C60 heteroarylene group, the Ar being selected from one of a substituted or unsubstituted C5 - C60 aryl group, a substituted or unsubstituted C3 - C60 heteroaryl group, and the - L-Ar is not selected from phenyl, biphenyl, or cyano substituted phenyl. When the compound provided by the invention is applied OLED devices, the efficiency of the device can be effectively improved, the driving voltage is reduced, and the compound is a good-performance electronic transmission material.

Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model

Most transcription factors were for a long time considered as undruggable targets because of the absence of binding pockets for direct targeting. HOXA9, implicated in acute myeloid leukemia, is one of them. To date, only indirect targeting of HOXA9 expres

Antimalarials with benzothiophene moieties as aminoquinoline partners

Malaria is a severe and life-threatening disease caused by Plasmodium parasites that are spread to humans through bites of infected Anopheles mosquitoes. Here, we report on the efficacy of aminoquinolines coupled to benzothiophene and thiophene rings in inhibiting Plasmodium falciparum parasite growth. Synthesized compounds were evaluated for their antimalarial activity and toxicity, in vitro and in mice. Benzothiophenes presented in this paper showed improved activities against a chloroquine susceptible (CQS) strain, with potencies of IC50 = 6 nM, and cured 5/5 Plasmodium berghei infected mice when dosed orally at 160 mg/kg/day x 3 days. In the benzothiophene series, the examined antiplasmodials were more active against the CQS strain D6, than against strains chloroquine resistant (CQR) W2 and multidrug-resistant (MDR) TM91C235. For the thiophene series, a very interesting feature was revealed: hypersensitivity to the CQR strains, resistance index (RI) of 1. This is in sharp contrast to chloroquine, indicating that further development of the series would provide us with more potent antimalarials against CQR strains.

Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group

The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and various electron-deficient aryl bromides as aryl sources, C5-(hetero)arylated thiophenes were synthesized in moderate to high yields, without cleavage of the thienyl C-Br bond. Moreover, sequential direct thienyl C5-arylation followed by Pd-catalysed direct arylation or Suzuki coupling at the C2-position allows to prepare 2,5-di(hetero)arylated thiophenes bearing two different (hetero)aryl units in only two steps. This method provides a green access to arylated thiophene derivatives as it reduces the number of steps to prepare these compounds and also the formation of wastes.

Palladium-catalyzed coupling reactions of bromothiophenes at the C-H bond adjacent to the sulfur atom with a new activator system, AgNO3/KF

(Chemical Equation Presented) Bromothiophene derivatives react with aryl iodides catalyzed by a palladium complex in the presence of a silver(I) nitrate/potassium fluoride system to induce coupling at the C-H bond, while the carbon-bromine bond is intact.

Structural selectivity of aromatic diamidines

Competition dialysis was used to study the interactions of 13 substituted aromatic diamidine compounds with 13 nucleic acid structures and sequences. The results show a striking selectivity of these compounds for the triplex structure poly dA:(poly dT)su

Antileishmanial activities of several classes of aromatic dications

Aromatic dicationic molecules possess impressive activity against a broad spectrum of microbial pathogens, including Pneumocystis carinii, Cryptosporidium parvum, and Candida albicans. In this work, 58 aromatic cations were examined for inhibitory activity against axenic amastigote-like Leishmania donovani parasites. In general, the most potent of the compounds were substituted diphenyl furan and thiophene dications. 2,5-Bis-(4-amidinophenyl)thiophene was the most active compound. This agent displayed a 50% inhibitory concentration (IC50) of 0.42 ± 0.08 μM against L. donovani and an in vitro antileishmanial potency 6.2-fold greater than that of the clinical antileishmanial dication pentamidine and was 155-fold more toxic to the parasites than to a mouse macrophage cell line. 2,4-Bis-(4-amidinopheny)furan was twice as active as pentamidine (IC50, 1.30 ± 0.21 μM), while 2,5-bis-(4-amidinopheny)furan and pentamidine were essentially equipotent in our in vitro antileishmanial assay. Carbazoles, dibenzofurans, dibenzothiophenes, and benzimidazoles containing amidine or substituted amidine groups were generally less active than the diphenyl furans and thiophenes. In all cases, aromatic dications possessing strong antileishmanial activity were severalfold more toxic to the parasites than to a cultured mouse macrophage cell line. These structure-activity relationships demonstrate the potent antileishmanial activity of several aromatic dications and provide valuable information for the future design and synthesis of more potent antiparasitic agents.