10243-15-9

Basic information

• Product Name: 3-BROMO-2-METHYL-BENZO[B]THIOPHENE
• Synonyms: 3-BROMO-2-METHYL-BENZO[B]THIOPHENE;3-BROMO-2-METHYL-1-BENZOTHIOPHENE;3-bromo-2-methyl-benzothiophene
• CAS NO: 10243-15-9
• Molecular Formula: C₉H₇BrS
• Molecular Weight: 227.12088
• Mol File: 10243-15-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 42-42.5 °C
• Boiling Point: 302°C at 760 mmHg
• Flash Point: 136.4°C
• Appearance: /
• Density: 1.561g/cm³
• Vapor Pressure: 0.00182mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3-BROMO-2-METHYL-BENZO[B]THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-METHYL-BENZO[B]THIOPHENE(10243-15-9)
• EPA Substance Registry System: 3-BROMO-2-METHYL-BENZO[B]THIOPHENE(10243-15-9)

Safety Data

• Hazardous Substances Data: 10243-15-9(Hazardous Substances Data)

Usage

General Description

3-Bromo-2-methyl-benzo[b]thiophene is a synthetic organic compound characterized by the presence of bromine, sulfur, and a methyl group attached to a benzo[b]thiophene molecular scaffold. Chemically, it typically comes under the class of organobromides and organosulfur compounds. Its extended name is benzo[b]thiophene, 3-bromo-2-methyl-, and it is often denoted by the CAS number 13257-48-4. 3-BROMO-2-METHYL-BENZO[B]THIOPHENE in its pure form is generally found to be light yellow in color. It has potential applications in organic synthesis as a chemical intermediate and is often utilized in the fields of pharmaceuticals and agrochemicals. Like many organobromides, it is assumed to be relatively reactive and should be handled with appropriate safety measures.

InChI:InChI=1/C9H7BrS/c1-6-9(10)7-4-2-3-5-8(7)11-6/h2-5H,1H3

Upstream product

• 1195-14-8 2-Methylbenzothiophene 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 74-88-4 methyl iodide 
• 95-15-8 Benzo[b]thiophene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 57642-62-3 2-methyl-3-phenylbenzothiophen 
• 4923-91-5 2,3-dimethylbenzothiophene 
• 137814-07-4 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene 
• 1195-14-8 2-Methylbenzothiophene 
• 137814-10-9 3,3’-(perfluorocyclobut-1-ene-1,2-diyl)bis(2-methylbenzo[b]thiophene) 
• 1344734-18-4 1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene 
• 1344734-27-5 C₂₅H₁₆F₆S₂ 

Relevant articles and documents

Thieme Chemistry Journal Awardees - Where are They Now? The Influence of Electron-Withdrawing Groups at the 2- and 2′-Positions of Dibenzothienylethenes on Molecular Switching

Three dibenzothienylethenes that carry a methyl, a trifluoromethyl, or a fluoro substituent in the 2- and 2′-position were synthesised in short multistep syntheses, respectively. The trifluoromethyl and fluoromethyl substituents significantly improve the absorption properties of the corresponding open and closed isomers (both in the UV-A and in the visible range). The increasing electron deficiency (i) enlarges the portion of the closed and coloured diarylethene isomer in the corresponding photostationary states and slows down the closing and opening isomerisation, (ii) the switching reactions, both closing and opening, are slowed down, and (iii) the switching quantum yields are lowered.

Diastereoselective self-assembly of a triple-stranded europium helicate with light modulated chiroptical properties

Chiroptical photoswitches are of increasing interest for their potential in advanced information technologies. Herein, an achiral bis-β-diketonate ligand (o-L) with a photoresponsive diarylethene moiety as a linker was designed, which co-assembled with Eu3+ions andR- andS-bis(diphenylphosphoryl)-1,10-binaphthyl (R/S-BINAPO) as chiral ancillaries to form dinuclear triple-stranded helicates, [Eu2(o-L)3(R/S-BINAPO)2]. The helicates in the enantiopure form were confirmed by1H,19F,31P NMR and DOSY NMR analyses. Furthermore, the mirror-image CD and CPL spectra also demonstrate the existence of stable ground- and excited-state chiralities in solution. When exposed to alternate ultraviolet and visible light, the helicates showed reversible color variations from colorless to purple, followed by the presence of light-triggered quadruple optical and chiroptical outputs, named CD, PL, CPL andglumswitches. With these light-modulated optical outputs, the possibility for the fabrication of IMPLICATION and INHIBIT logic gates was discussed.

Reversible Photomodulation of Electronic Communication in a π-Conjugated Photoswitch-Fluorophore Molecular Dyad

The extent of electronic coupling between a boron dipyrromethene (BODIPY) fluorophore and a diarylethene (DAE) photoswitch has been modulated in a covalently linked molecular dyad by irradiation with either UV or visible light. In the open isomer, both moieties can be regarded as individual chromophores, while in the closed form the lowest electronic (S0→S1) transition of the dyad is slightly shifted, enabling photomodulation of its fluorescence. Transient spectroscopy confirms that the dyad behaves dramatically different in the two switching states: while in the open isomer it resembles an undisturbed BODIPY fluorophore, in the closed isomer no fluorescence occurs and instead a red-shifted DAE behavior prevails.

Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions with indium organometallics: Synthesis and photochemical studies

The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R3In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R3In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process.

5-HETEROARYL-PYRIDIN-2-AMINE CONFOUNDS AS NEUROPEPTIDE FF RECEPTOR ANTAGONISTS

The present invention relates to novel aminopyridine derivatives of the general formula (I) and pharmaceutical compositions comprising these compounds, as well as their therapeutic use, particularly as neuropeptide FF (NPFF) receptor antagonists, including, e.g., for the treatment or prevention of pain, opioid-induced hyperalgesia, or addiction.