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
• Article Data: 13

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

General Description

3,5-Dibromothiophene-2-carbaldehyde is a chemical compound with the molecular formula C6H3Br2OS. It is a derivative of thiophene and contains two bromine atoms and an aldehyde functional group. 3,5-DIBROMOTHIOPHENE-2-CARBALDEHYDE is commonly used in the synthesis of pharmaceuticals, agrochemicals, and materials science applications. It is an important intermediate in the production of various heterocyclic compounds and has been studied for its potential antimicrobial and anticancer properties. Additionally, 3,5-Dibromothiophene-2-carbaldehyde is known for its use in organic synthesis and has been utilized as a reagent in numerous chemical reactions.

Upstream product

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

Downstream Products

• 107938-07-8 3-bromo-5-phenyl-2-thiophenecarboxaldehyde 
• 675872-43-2 2-(hydroxymethyl)-3,5-dibromothiophene 
• 675872-45-4 3,5-dibromo-2-trityloxymethylthiophene 
• 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 
• 308255-23-4 2-(3-bromo-5-phenylthiophen-2-yl)[1,3]dioxolane 
• 295343-51-0 3-(2-(2-methyl-5-phenylthiophen-3-yl)perfluorocyclopent-1-en-1-yl)-5-phenylthiophene-2-carbaldehyde 
• 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 
• 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 
• 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 
• 1174754-33-6 4-(4-bromo-5-(dimethoxymethyl)thiophen-2-yl)-N,N-dimethylbenzenamine 

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.

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.

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.