23688-07-5

Basic information

• Product Name: 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE
• Synonyms: 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE;3,5-DIBROMO-2-THIOPHENECARBOXALDEHYDE;D90005
• CAS NO: 23688-07-5
• Molecular Formula: C₅H₂Br₂OS
• Molecular Weight: 269.94
• Mol File: 23688-07-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE(23688-07-5)
• EPA Substance Registry System: 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE(23688-07-5)

Safety Data

• Hazardous Substances Data: 23688-07-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of heterocyclic compounds with potential therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is used as a key intermediate in the production of various agrochemicals, helping to create effective solutions for pest control and crop protection.
Used in Materials Science:
3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is utilized in materials science as a component in the development of new materials with specific properties, such as those with antimicrobial or anticancer capabilities.
Used in Organic Synthesis:
As a reagent in organic synthesis, 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is used to facilitate numerous chemical reactions, contributing to the creation of a wide range of chemical products.
Used in Antimicrobial Applications:
3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is studied for its potential antimicrobial properties, making it a candidate for use in applications that require the inhibition of microbial growth.
Used in Anticancer Research:
Due to its potential anticancer properties, 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is being investigated for use in cancer research and the development of novel therapeutic agents.

Upstream product

• 3140-93-0 2,3-dibromothiophen 
• 68-12-2 N,N-dimethyl-formamide 
• 3141-27-3 2,5-dibromothiophen 
• 3140-92-9 2,4-dibromothiophene 
• 3141-24-0 2,3,5-tribromothiophene 

Downstream Products

• 675872-43-2 2-(hydroxymethyl)-3,5-dibromothiophene 
• 1174754-33-6 4-(4-bromo-5-(dimethoxymethyl)thiophen-2-yl)-N,N-dimethylbenzenamine 
• 1174754-36-9 5-(4-(dimethylamino)phenyl)-3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(trimethylsilyl)thiophen-3-yl)cyclopent-1-enyl)thiophene-2-carbaldehyde 
• 308255-25-6 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-hydroxy-1-pentyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 
• 308255-24-5 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(2,5-dioxolanyl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 
• 295343-51-0 3-(2-(2-methyl-5-phenylthiophen-3-yl)perfluorocyclopent-1-en-1-yl)-5-phenylthiophene-2-carbaldehyde 
• 308255-23-4 2-(3-bromo-5-phenylthiophen-2-yl)[1,3]dioxolane 
• 249932-09-0 (S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene 
• 675872-45-4 3,5-dibromo-2-trityloxymethylthiophene 

Relevant articles and documents

Synthesis of 2-Substituted 3,5-Dibromothiophenes via a Rearrangement Reaction: A New Example of a Base-Catalyzed Halogen Dance Reaction

The reaction of 2,3-dibromothiophene with 1 equivalent of lithium diisopropylamide at -80 deg C, followed by addition of an electrophile (methyl iodide, methanol, allyl bromide, dimethylformamide, cyclohexanone) gives 2-substituted 3,5-dibromothiophenes selectively and in high yields.The substitution pattern of all products was confirmed by unambiguous assignment of all C-atoms via 13C-NMR spectrometry.

5-[5-(PIPERIDIN-4-YL)THIENO[3,2-C]PYRAZOL-2-YL]INDAZOLE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS FOR SPLICING NUCLEIC ACIDS AND FOR THE TREATMENT OF PROLIFERATIVE DISEASES

The present disclosure features compounds e.g. of formula (I-a) and similar compounds e.g. of formulae (l-g), (l-i), (l-j), (III), (lll-a), (III- b) and (IV) disclosed herein and other related compounds, and pharmaceutical compositions thereof. The present disclosure further discloses said compounds and their compositions for use in methods of modulating nucleic acid splicing, as well as said compounds for use in methods of treating e.g.: ? proliferative diseases, such as e.g. cancer, benign neoplasms or angiogenesis, ? neurological diseases or disorders, such as e.g. Huntington's disease, ? autoimmune diseases or disorders, immunodeficiency diseases or disorders, lysosomal storage disease or disorder, cardiovascular diseases or disorders, metabolic diseases or disorders, respiratory diseases or disorders, renal diseases or disorders, or infectious diseases. Exemplary compounds are e.g. 5-[5-(piperidin-4-y l)thieno[3,2- c]pyrazol-2-yl]indazole and 5-[2-(piperidin-4-yl)-[1,2,4]triazolo[3,2-b] [1,3]thiazol-5-yl]indazole derivatives and related compounds.

Mechanistic Insights into the Triplet Sensitized Photochromism of Diarylethenes

Operating photoswitchable molecules repetitively and reliably is crucial for most of their applications, in particular in (opto)electronic devices, and related to reversibility and fatigue resistance, which both critically depend on the photoisomerization mechanism defined by the substitution pattern. Two diarylethene photoswitches bearing biacetyl triplet sensitizers either at the periphery or at the core were investigated using both stationary as well as transient UV/Vis absorption spectroscopy ranging from the femtosecond to the microsecond time scale. The diarylethene with two biacetyl moieties at the periphery is switching predominantly from the triplet excited state, giving rise to an enhanced fatigue resistance. In contrast, the diarylethene bearing one diketone at the photoreactive inner carbon atom cyclizes from the singlet excited state and shows significantly higher quantum yields for both cyclization and cycloreversion.

Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.

Light-Activated Sensitive Probes for Amine Detection

Our new, simple, and accurate colorimetric method is based on diarylethenes (DAEs) for the rapid detection of a wide range of primary and secondary amines. The probes consist of aldehyde- or ketone-substituted diarylethenes, which undergo an amine-induced decoloration reaction, selectively to give the ring-closed isomer. Thus, these probes can be activated at the desired moment by light irradiation, with a sensitivity that allows the detection of amines at concentrations as low as 10?6m in solution. In addition, the practical immobilization of DAEs on paper makes it possible to detect biogenic amines, such as cadaverine, in the gas phase above a threshold of 12 ppbv within 30 seconds.

5-alkylidenethiophen-2(5H)-ones as biofilm inhibitors

A number of thiophen-2(5H)-ones with different substituents in the 3-, 4-and 5-position have been synthesized and tested as inhibitors of biofilm production by the marine bacterium Vibrio harveyi BB120. Concentrations that inhibited 50% or 90% of biofilm formation (BIC50, BIC90) and of plantonic growth (PIC50, PIC90) are reported.

New fluorescent bis-dithienylethene (DTE)-based bipyridines as reverse interrupters: Single vs. double photochromism

The synthesis and characterization of a series of fluorescent bis-dithienylethene (DTE)-based bipyridines, where the donor (D) and acceptor (A) groups are located on the same thiophene ring of the DTE unit, and their zinc(ii) and rhenium(i) complexes are reported. Their photochromic properties have been investigated by UV-visible and 1H NMR spectroscopy. These studies reveal that in non-polar solvents it is possible to modulate the photoreactivity, single vs. double ring-closure, by changing the nature of the donor group. The solvent effect, as well as the influence of the organometallic moieties on the photochromic behavior of these molecules, is also discussed. Finally, upon photoconversion to the photostationary state (PSS), a quenching of fluorescence is observed for the bipyridine ligands, due to disruption of the conjugation upon ring-closing.

THIOPHENE DERIVATIVE

The present invention provides a compound represented by the formula (I) or its salt, solvate, or physiologically functional derivative; and a pharmaceutical composition which is useful for treatment or prevention of conditions or disorders having sensitivity to selective androgen receptor modulation, the composition comprising the above-described compound; among others:

Carbonic anhydrase inhibitors

Compounds of the following formula are disclosed: Compounds of Formula I are the topic of this invention: STR1 Wherein G, J and the two atoms of the thiophene ring to which they are attached form a six-membered ring chosen from STR2 The compounds are usef

Halogen Dance Reactions at Thiophenes and Furans: Selective Access to a Variety of New Trisubstituted Derivatives

LDA-induced halogen migrations and their selective preventions on various bromo substituted thiophenes and furans gave upon reaction with electrophiles access to a large variety of new tri-substituted derivatives.Extension of HD-methodology to 5,5'-dibromo-2,2'-bithiophene enabled for the first time control of selective mono- and double halogen migration.