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3,5-DIBROMO-2-METHYLTHIOPHENE is an organic compound characterized by its unique molecular structure, featuring two bromine atoms at the 3rd and 5th positions, a methyl group at the 2nd position, and a sulfur atom at the 2nd position as well. 3,5-DIBROMO-2-METHYLTHIOPHENE is known for its potential applications in various chemical and pharmaceutical processes due to its distinct properties.

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  • 29421-73-6 Structure
  • Basic information

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

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

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 29421-73-6(Hazardous Substances Data)

29421-73-6 Usage

Uses

Used in Chemical Synthesis:
3,5-DIBROMO-2-METHYLTHIOPHENE is used as a reagent for the preparation of arylthiophene-substituted norbornadienes. Its unique structure allows for the creation of complex organic molecules that can be utilized in various industries, such as pharmaceuticals and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-DIBROMO-2-METHYLTHIOPHENE is used as a key intermediate in the synthesis of various therapeutic compounds. Its ability to form arylthiophene-substituted norbornadienes makes it a valuable building block for the development of novel drugs with potential applications in treating various diseases and medical conditions.
Used in Materials Science:
3,5-DIBROMO-2-METHYLTHIOPHENE can also be employed in the development of new materials with specific properties, such as improved conductivity, stability, or reactivity. Its unique molecular structure allows for the creation of materials with tailored characteristics, making it a valuable asset in the field of materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 29421-73-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,4,2 and 1 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 29421-73:
(7*2)+(6*9)+(5*4)+(4*2)+(3*1)+(2*7)+(1*3)=116
116 % 10 = 6
So 29421-73-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H4Br2S/c1-3-4(6)2-5(7)8-3/h2H,1H3

29421-73-6 Well-known Company Product Price

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  • TCI America

  • (D3999)  3,5-Dibromo-2-methylthiophene  >95.0%(GC)

  • 29421-73-6

  • 5g

  • 820.00CNY

  • Detail
  • TCI America

  • (D3999)  3,5-Dibromo-2-methylthiophene  >95.0%(GC)

  • 29421-73-6

  • 25g

  • 2,850.00CNY

  • Detail

29421-73-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,5-DIBROMO-2-METHYLTHIOPHENE

1.2 Other means of identification

Product number -
Other names EINECS 249-617-9

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:29421-73-6 SDS

29421-73-6Relevant articles and documents

A dual-mode visual detector for toxic hydrazine

Branda, Neil R.,Kaur, Brahmjot,Raza, Rameez

, p. 22835 - 22841 (2021)

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 ferrocene-functionalized unsymmetrical benzo[b]thienyl- thienylethene photoswitch with a cyclopentene core

Zuckerman, Nathaniel B.,Kang, Xiongwu,Chen, Shaowei,Konopelski, Joseph P.

, p. 1482 - 1485 (2013)

A new and potentially general synthetic route toward unsymmetrical benzo[b]thienyl-thienylethene compounds is described, with specific focus on conjugation of a ferrocene to the benzo[b]thiophene subunit. The route proceeds in an overall yield of 17%. Copyright

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

Maag, Roman,Siegel, Jay S.

, p. 2117 - 2122 (2016)

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.

Synthesis and characterization of 5,5′-bis-silylated dithienylethene as a new building block of novel photochromic periodic mesoporous organosilicas

Abboud, Mohamed

, p. 2195 - 2204 (2020)

Pure bis-silylated dithienylethene (DTE) 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(triethoxysilyl)thiophen-3-yl)cyclopent-1-enyl)-2-methyl-5-(triethoxysilyl)thiophene was prepared from 3-(3,3,4,4,5,5-hexafluoro-2-(5-iodo-2-methylthiophen-3-yl)cyclopent-1-enyl)-5-iodo-2-methylthiophene by iodine–lithium exchange. The synthesis and purification method were optimized after many attempts of different coupling methods and purification techniques to ovoid the hydrolysis and self-condensation reaction and to obtain a pure product. The obtained bis-silylated dithienylethene (BS-DTE) is a versatile building block for potential applications, such as synthesis of new photochromic periodic mesoporous organosilica (PPMO). The structure of the obtained precursor was characterized by 1H, 13C and 29Si liquid NMR. Many attempts have been performed to prepare DTE-PMO but, the C–Si bond in the final material was fragile and could not resist to the hydrothermal treatment during the synthesis. The thermal stability of DTE-PMO will be studied in a future work.

In Situ Photoconversion of Multicolor Luminescence and Pure White Light Emission Based on Carbon Dot-Supported Supramolecular Assembly

Wu, Huang,Chen, Yong,Dai, Xianyin,Li, Peiyu,Stoddart, J. Fraser,Liu, Yu

, p. 6583 - 6591 (2019)

Constructing multicolor photoluminescence materials that allow for the integration of suitable external stimuli in order to control luminescence color conversions is a challenging objective. Multicolor luminescent output that is regulated in an in situ photo-controlled manner is not a common phenomenon. Herein, a photoluminescent supramolecular assembly, prepared in two stages, is described that displays in situ photo-tuning broad-spectrum output. Benefiting from the reversible photo-switched constitutional interconversion of diarylethenes, the fluorescence of a guest molecule, styrylpyridinium-modified diarylethene, can be switched on/off by alternating ultraviolet and visible light irradiation. Upon complexation of this guest with a host, cucurbit[8]uril, the fluorescence intensity of the resulting binary supramolecular nanofiber shows a drastic enhancement when compared with that of the free guest, which can also be quenched and recovered reversibly by light irradiation. Significantly, such cationic supramolecular nanofibers also interact with anionic carbon dots to form broad-spectrum output ternary supramolecular assemblies, the fluorescence of which can be changed efficiently from yellow to blue in an in situ photo-controlled manner. Pure white light emission can be realized expediently in the luminescence color-conversion process. The use of light as an external stimulus to regulate fluorescent color conversion provides us with an opportunity to design and construct more advanced anti-counterfeiting materials as well as visual display instruments.

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

Lim, Seon-Jeong,An, Byeong-Kwan,Sang, Don Jung,Chung, Myung-Ae,Soo, Young Park

, p. 6346 - 6350 (2004)

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).

Creating coordination-based cavities in a multiresponsive supramolecular gel

Wei, Shi-Chao,Pan, Mei,Fan, Yuan-Zhong,Liu, Haoliang,Zhang, Jianyong,Su, Cheng-Yong

, p. 7418 - 7427 (2015)

Abstract Creating cavities in varying levels, from molecular containers to macroscopic materials of porosity, have long been motivated for biomimetic or practical applications. Herein, we report an assembly approach to multiresponsive supramolecular gels by integrating photochromic metal-organic cages as predefined building units into the supramolecular gel skeleton, providing a new approach to create cavities in gels. Formation of discrete O-Pd2L4 cages is driven by coordination between Pd2+ and a photochromic dithienylethene bispyridine ligand (O-PyFDTE). In the presence of suitable solvents (DMSO or MeCN/DMSO), the O-Pd2L4 cage molecules aggregate to form nanoparticles, which are further interconnected through supramolecular interactions to form a three-dimensional (3D) gel matrix to trap a large amount of solvent molecules. Light-induced phase and structural transformations readily occur owing to the reversible photochromic open-ring/closed-ring isomeric conversion of the cage units upon UV/visible light radiation. Furthermore, such Pd2L4 cage-based gels show multiple reversible gel-solution transitions when thermal-, photo-, or mechanical stimuli are applied. Such supramolecular gels consisting of porous molecules may be developed as a new type of porous materials with different features from porous solids. Metal-organic cages were utilized as building units for the first time to generate supramolecular gels, providing a synthetic approach to cavity-containing gels that display multi-responsiveness towards environmental physical and chemical stimuli (see figure).

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

Adams, J?rg,Dahle, Sebastian,Hübner, Eike G.,Lederle, Felix,Maus-Friedrichs, Wolfgang,Nagorny, Sven,Schmidt, Andreas,Udachin, Viktor,Weingartz, Thea

, p. 3178 - 3189 (2021/07/02)

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.

The mechanodonor-acceptor coupling (MDAC) approach for unidirectional multi-state fluorochromism

Gu, Luyan,Zhang, Lujia,Luo, Xiao,Zheng, Ying,Ye, Zhiwei,Lv, Meng,Chen, Jinquan,Chen, Chunlai,Xiao, Yi,Zhu, Weihong,Qian, Xuhong,Yang, Youjun

, p. 253 - 262 (2021/01/06)

Uni-directional multi-state fluorochromic scaffolds are valuable photofunctional molecules and yet scarce. We report a general approach for their design, i.e., mechanodonor-acceptor coupling (MDAC). A photochromic molecule is a mechanodonor, due to its capability to convert photonic energy into mechanical force. Upon proper coupling, it can be used to drive a mechanochromic molecule for uni-directional multi-state fluorochromism. The embodiment of this approach is a rhodamine-dithienylethylene hydride (RDH), which has been successfully employed in super-resolution localization microscopy[Figure not available: see fulltext.]

Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches

Kolmar, Theresa,Büllmann, Simon M.,Sarter, Christopher,H?fer, Katharina,J?schke, Andres

supporting information, p. 8164 - 8173 (2021/03/08)

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.

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