29421-73-6

Basic information

• Product Name: 3,5-DIBROMO-2-METHYLTHIOPHENE
• Synonyms: 3,5-DIBROMO-2-METHYLTHIOPHENE;2-METHYL-3,5-DIBROMO-THIOPHENE
• CAS NO: 29421-73-6
• Molecular Formula: C₅H₄Br₂S
• Molecular Weight: 255.96
• EINECS: 249-617-9
• Product Categories: Thiophene&Benzothiophene;Thiophens
• Mol File: 29421-73-6.mol
• Article Data: 65

Chemical Properties

• Melting Point: -15°C(lit.)
• Boiling Point: 230°C(lit.)
• Flash Point: 94 °C
• Appearance: /
• Density: 2.006 g/cm³
• Vapor Pressure: 0.0928mmHg at 25°C
• Refractive Index: 1.6120-1.6160
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 3,5-DIBROMO-2-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMO-2-METHYLTHIOPHENE(29421-73-6)
• EPA Substance Registry System: 3,5-DIBROMO-2-METHYLTHIOPHENE(29421-73-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 29421-73-6(Hazardous Substances Data)

Usage

Uses

3,5-Dibromo-2-methylthiophene is a useful reagent for the preparation of arylthiophene-substituted norbornadienes.

InChI:InChI=1/C5H4Br2S/c1-3-4(6)2-5(7)8-3/h2H,1H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 75-15-0 carbon disulfide 
• 3140-93-0 2,3-dibromothiophen 
• 74-88-4 methyl iodide 
• 3141-27-3 2,5-dibromothiophen 

Downstream Products

• 348639-14-5 3-bromo-2-methyl-5-trimethylsilylethynylthiophene 
• 730985-76-9 3-bromo-5-(4-cyanophenyl )-2-methylthiophene 
• 30319-05-2 3-bromo-2-methylthiophene 
• 1332306-30-5 3-bromo-2-methyl-5-(phenylethynyl)thiophene 
• 1388722-82-4 C₃₅H₂₆F₆INO₂S₂ 
• 1229936-73-5 4,4,5,5-tetramethyl-2-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-enyl)-1,3,2-dioxaborolane 
• 1229936-89-3 (2R,3S,5R)-5-(4-amino-6-methyl-5-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol 
• 162607-23-0 2,5-dimethylthien-3-ylboronic acid 
• 31819-37-1 3-bromo-2,5-dimethylthiophene 
• 1229936-57-5 3-(2-bromocyclopent-1-enyl)-2-methyl-5-phenylthiophene 
• 61285-25-4 3-bromo-2-methyl-5-phenylthiophene 

Relevant articles and documents

A dual-mode visual detector for toxic hydrazine

Hydrazine (N2H4) is one of the commonly used chemical reagents in numerous industries and applications but its toxicity to humans poses a need to develop simple visual detection methods. Herein, we demonstrate a novel dual-mode system to detect and simultaneously consume hydrazine in vapour and solution by using a small photoresponsive molecule that has altered optical response (both colourimetric and fluorescent) after reacting with hydrazine. This journal is

Synthesis of a Five-Fold-Differentiated 1,3,5,7,9-Pentasubstituted Corannulene: A Maximal Labeling Problem in the Context of Corannulene

This work defines a maximally labeled isomer problem in the context of 1,3,5,7,9-pentasubstituted corannulenes and explores two new synthetic strategies for the construction of key C-C bonds in the corannulene nucleus: a) a Diels-Alder cycloaddition of thiophene dioxide and acenaphthene fragments; b) a manganese-mediated reductive coupling of benzylic halides, which tolerates carboxy ester functionality. It advances the area of curved aromatics based on corannulene by setting a new family of targets for chemical synthesis and providing additional general synthetic tools.

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Photoswitchable organic nanoparticles and a polymer film employing multifunctional molecules with enhanced fluorescence emission and bistable photochromism

Get turned on: Fluorescent photochromic organic nanoparticles (FPONs) of 1 (see picture) show a strongly enhanced fluorescence emission with increasing concentration and bistable photochromism. High-contrast on/off fluorescence switching has been successfully implemented in size-tuned FPONs of 1 and also in a photo-rewritable polymer film highly loaded with 1. (Chemical equation presented).

Switchable Mesomeric Betaines Derived from Pyridinium-Phenolates and Bis(thienyl)ethane

Syntheses of push–pull substituted non-symmetric bis(thienyl)ethenes (BTEs) possessing a central perfluorocyclopentene core are described. The substituent effects of anisole, phenole, and phenolate as well as pyridine, pyridinium, and N-methylpyridinium substituents, joined through their 3- or 4-positions to the central BTE core, respectively, cover the range from very strongly electron-donating [σ(4-phenolate)=?1.00] to extremely strongly electron-withdrawing [σ(pyridinium-4-yl)=+2.57] in the title mesomeric betaines. The different isomers possessing 4-yl/4-yl, 4-yl/3-yl and 3-yl/3-yl substituents represent different combinations of conjugated and cross-conjugated partial structures and cause different spectroscopic properties. In addition, through-space conjugation between the 2- and 2′-position of the thiophenes can be observed which circumvents the charge-separation of through-bond cross-conjugation. The BTE possessing the push–pull chromophore consisting of 3-anisole and 4-pyridinium substituents (24) displays the best extinction coefficients within the series of compounds described here (?=33.8/15.7 L/mol ? cm), while the mesomeric betaine possessing an N-methylpyridinium-4-yl and a 4-phenolate substituent (29) displays considerable bathochromic shifts to λmax=724 nm in its closed form.

Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches

Nucleosidic and oligonucleotidic diarylethenes (DAEs) are an emerging class of photochromes with high application potential. However, their further development is hampered by the poor understanding of how the chemical structure modulates the photochromic properties. Here we synthesized 26 systematically varied deoxyuridine- and deoxycytidine-derived DAEs and analyzed reaction quantum yields, composition of the photostationary states, thermal and photochemical stability, and reversibility. This analysis identified two high-performance photoswitches with near-quantitative, fully reversible back-and-forth switching and no detectable thermal or photochemical deterioration. When incorporated into an oligonucleotide with the sequence of a promotor, the nucleotides maintained their photochromism and allowed the modulation of the transcription activity of T7 RNA polymerase with an up to 2.4-fold turn-off factor, demonstrating the potential for optochemical control of biological processes.