13191-36-1

Basic information

• Product Name: 2,5-DIBROMO-3-METHYLTHIOPHENE
• Synonyms: 2,5-DIBROMO-3-METHYLTHIOPHENE;2,5-DIBROMO-3-METHYLTHIOPHENE 98%;Einecs 236-147-4
• CAS NO: 13191-36-1
• Molecular Formula: C₅H₄Br₂S
• Molecular Weight: 255.96
• EINECS: 236-147-4
• Product Categories: Thiophene;Thiophens
• Mol File: 13191-36-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 226-230°C
• Flash Point: 226-230°C
• Appearance: /
• Density: 1,972 g/cm3
• Vapor Pressure: 0.101mmHg at 25°C
• Refractive Index: 1.6130
• Storage Temp.: 2-8°C
• Sensitive: Light Sensitive
• BRN: 108894
• CAS DataBase Reference: 2,5-DIBROMO-3-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBROMO-3-METHYLTHIOPHENE(13191-36-1)
• EPA Substance Registry System: 2,5-DIBROMO-3-METHYLTHIOPHENE(13191-36-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/38-41-38-22
• Safety Statements: 26-36/37/39-39
• RIDADR: UN 2810 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 13191-36-1(Hazardous Substances Data)

Usage

Uses

2,5-Dibromo-3-methylthiophene, is a building block used in chemical synthesis of various compounds.

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

Upstream product

• 616-44-4 3-Methylthiophene 

Downstream Products

• 492-97-7 2,2'-Bithiophene 
• 113386-76-8 3'-methyl-2,2':5',2-terthiophene 
• 14282-76-9 2-bromo-3-methylthiophene 
• 1435937-73-7 (5-bromo-4-methylthiophen-2-yl)(thiophen-2-yl)methanone 
• 40808-46-6 4-methyl-2,5-diphenylthiophene, 
• 439901-89-0 triphenyl((2,5-dibromothiophen-3-yl)methyl)phosphonium bromide 

Relevant articles and documents

Synthesis and properties of regioregular poly(3-substituted thiophene) bearing disiloxane moiety in the substituent. remarkably high solubility in hexane

Regioregular poly(3-substituted thiophene) derivative bearing pentamethyldisiloxane moiety at the 3-substituent is prepared by nickel-catalyzed polymerization reactions with dehydrobrominative or debrominative generation of the organometallic monomer. The monomer precursors 2-bromo-3-(4- pentamethyldisiloxybutan-1-yl)thiophene (1a) and 2,5-dibromo- 3-(4-pentamethyldisiloxybutan-1-yl)thiophene (1b) are prepared from 3-methylthiophene with 45 steps in overall good yields. Treatment of 1a with TMPMgCl￠LiCl at room temperature for 3 h forms an organometallic monomer and following the addition of a nickel catalyst affords the corresponding polythiophene bearing a disiloxane moiety in the side chain. The reaction of 1b with Grignard reagent leads to the similar monomer and addition of a catalytic amount of [NiCl2(dppe)] also affords polythiophene in highly regioregular manners. The obtained polythiophene is found to be dissolved in a hydrocarbon such as hexane.

Control of vertical distribution of thiophene-based copolymers containing 4,7-Dithien-2-yl-benzo[C][1,2,5]thiadiazole and 3,6-Dithien-2-yl-pyrrolo[3,4-C]pyrrole-1,4(2H,5H)-dione as Side Groups for Photovoltaics

Four new D—A type copolymers with 2D-conjugated side-chain identified PfToBT, PbToBT, PfTDPP and PbTDPP, containing two acceptors 4,7-dithien-2-yl-benzo[c][1,2,5]thiadiazole (DTBT), and diketopyrrolopyrrole (DPP) linked by thiophene donors, are obtained using Pd-catalyzed Stille-coupling reaction. These polymers show a broad visible-near-infrared absorption band (Eg?=?1.79–1.66?eV) and possess a relatively low-lying HOMO level at ?5.34 to ?5.12?eV. All the polymer:PC70BM blend films showed edge-on structure and have similar dπ-spacing values. According to the structure of conjugated side-chain, the vertical distributions of polymer chains and PC70BM within the BHJ (bulk heterojunction) were different. When DPP used as an acceptor, conjugated side chains of the polymer coexisted with PC70BM in same position. The BHJ film prepared from PfToBT, PbToBT had a discontinuous network between polymer and PC70BM, whereas films from PfTDPP and PbTDPP formed continuous and evenly distributed network between them. This optimized vertical morphology promotes hole transport along respective pathways of polymers and fullerenes in the vertical direction, leading to high JSC. PbTDPP shows PCE up to 2.9% (Jsc of 9.4?mA/cm2, Voc of 0.68 V, and FF of 0.44).

Use of poly(3-methylthio)thiophene blends for direct laser tracing and bulk heterojunction solar cells

In this article we demonstrate the use of a blend made of two regioregular polythiophenic derivatives, namely poly(3-methylthio)thiophene and poly(3-hexyl)thiophene, to obtain conductive traces by the simple laser exposure of their thin films to a suitable laser source. The polymeric blend was also tested as a photoactive layer for BHJ solar cells, showing an improved surface morphology and a wider absorption spectrum, thus resulting in an enhanced photovoltaic performance. In the standard condition normally used for the cell preparation, we obtained a 3.16% power conversion efficiency. The device showed good reproducibility and stability over time.

1,2,3-Triazolyl functionalized thiophene, carbazole and fluorene based A-: Alt -B type π-conjugated copolymers for the sensitive and selective detection of aqueous and vapor phase nitroaromatics (NACs)

A series of highly emissive π-conjugated A-alt-B type copolymers (P1-P3) appended with a 1,2,3-triazole moiety was synthesized via Suzuki polymerization. The well-defined and soluble π-conjugated copolymers were characterized via multinuclear NMR spectroscopy and tetradetector GPC studies, showing a molecular weight (Mn) in the range of 16.4-20.1 kDa with a polydispersity index in the range of 1.25-1.42. The synthesized emissive π-conjugated polymer probes were explored as fluorescent chemosensors for nitroaromatic compounds (NACs) in solution, vapor and contact mode. Detailed photophysical and sensing studies were performed to understand the polymer-NAC interaction, inducing the selective fluorescence quenching of the π-conjugated polymer probes through the photoinduced electron transfer (PET) mechanism. All the polymeric probes (P1-P3) were highly reversible in nature with NACs, and thus could be reused multiple times. The limit of detection of the probes towards nitroaromatics was found to be in the range of 120-200 ppb with a high association constant in the order of 104 M-1. Furthermore, test paper kits were also fabricated, which allowed the trace detection of picric acid by the naked eye, making it a practical means for the quick, easy and inexpensive on-site detection of NAC-based explosives.

Preparation method 2, 5 - dibromo -3 - methylthiophene

The invention discloses a preparation method of 2,5-dibromo-3-thiotolene shown as a formula (II). The method comprises the followings steps that the preparation method of the 2,5-dibromo-3-thiotolene shown as the formula (II) is characterized in that the method is performed through the following steps that 3-thiotolene shown as a formula (I) is used as a raw material; a brominating agent of potassium bromide is added; the mixture is stirred and mixed uniformly in a mixed solution of acetic acid and water; a brominating agent of ZnAl-BrO3-LDHs is slowly added at 10 to 50 DEG C; continuous stirring is performed for reaction for 2h; obtained reaction liquid is subjected to aftertreatment to obtain the 2,5-dibromo-3-thiotolene shown as the formula (II); the mass quantity ratio of the 3-thiotolene shown as the formula (I) to the ZnAl-BrO3-LDHs to the potassium bromide is 1:1.3:(1.6 to 1.9). The preparation method has the advantages that the reaction conditions are mild; the used brominating reagent is a solid matter, is cheap, is easily obtained and achieves an environment-friendly effect; the reaction operation is simple; the aftertreatment is convenient; the target product yield is high; the side reactions are few. The formulas are shown in the specification.