162607-17-2

Basic information

• Product Name: 5-BROMOTHIOPHENE-2-BORONIC ACID
• Synonyms: 2-BROMOTHIOPHENE-5-BORONIC ACID;5-BROMO-2-THIENYLBORONIC ACID;5-BROMO-2-THIOPHENEBORONIC ACID;AKOS BRN-0181;AKOS 92296;5-BROMOTHIOPHENEBORONIC ACID;5-BROMOTHIOPHENE-2-BORONIC ACID;5-BROMOTHIEN-2-YLBORONIC ACID
• CAS NO: 162607-17-2
• Molecular Formula: C₄H₄BBrO₂S
• Molecular Weight: 206.85
• Product Categories: Azoles;blocks;BoronicAcids;Bromides;Thiophene&Benzothiophene;Boronic acids;B (Classes of Boron Compounds);Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Boronic Acids;Boronic Acids and Derivatives;Heteroaryl
• Mol File: 162607-17-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 95-100 °C(lit.)
• Boiling Point: 342.3 °C at 760 mmHg
• Flash Point: 160.8 °C
• Appearance: /solid
• Density: 1.87 g/cm³
• Vapor Pressure: 2.93E-05mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: 0-6°C
• PKA: 8.20±0.53(Predicted)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: 5-BROMOTHIOPHENE-2-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOTHIOPHENE-2-BORONIC ACID(162607-17-2)
• EPA Substance Registry System: 5-BROMOTHIOPHENE-2-BORONIC ACID(162607-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 162607-17-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Reactant involved in:Suzuki coupling reactions for the synthesis of benzotriazole-containing organic sensitizers and meso-Polyarylamide-BODIPY hybridsSuzuki-Miyaura coupling for the synthesis of ratanhineMicrowave-assisted Sonogashira reactions for the synthesis of ethynylarylboronates

InChI:InChI=1/C4H4BBrO2S/c6-4-2-1-3(9-4)5(7)8/h1-2,7-8H

Upstream product

• 19162-80-2 5-bromo-[2]thienyl lithium 
• 60-29-7 diethyl ether 
• 688-74-4 boric acid tributyl ester 
• 3141-27-3 2,5-dibromothiophen 
• 6165-68-0 thiophene boronic acid 
• 121-43-7 Trimethyl borate 

Downstream Products

• 31161-46-3 2-benzoyl-5-bromothiophene 
• 1312457-61-6 5'-{4-(N,N-diphenylamino)stylyl}-2,2'-bithiophene-5-carbaldehyde 
• 1239370-98-9 potassium (5-bromothiophen-2-yl)trifluoroboranuide 
• 138565-27-2 2-phenyl-5-(pyridin-2-yl)thiophene 
• 927384-46-1 5-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)thiophene 
• 29488-24-2 2-Bromo-5-phenyl-thiophene 
• 1352915-40-2 4-(5-boronic acid thiophen-2-yl)triphenylamine 
• 1313392-39-0 5-bromothiophen-2-ol 
• 1003-09-4 2-bromothiophene 

Relevant articles and documents

Covalent functionalization of graphene with polythiophene through a Suzuki coupling reaction

In our tentative previous work, graphene was covalently functionalized by hexylbenzene and poly(9,9-dihexylfluorene) (PF) through a Suzuki coupling reaction. In this paper, thiophene and polythiophene (PTH) were grafted to brominated graphene (Br-Gra) in the same polymeric method. The obtained conjugated system of modified graphene was characterized by various techniques, including Fourier transform-infrared (FT-IR), ultraviolet-vis (UV-vis), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), fluorescence emission spectra, 1H-NMR spectra, and Raman spectroscopy. All the results revealed that thiophene and PTH were successfully grafted to the graphene. What's more, a colour change of their solution (Br-Gra doesn't dissolve in THF, while both thiophene grafted graphene (Gra-3TH) and PTH grafted graphene (Gra-PT) dissolve in THF, and exhibit a black and green color in THF respectively), which is caused by an electron-energy transfer between graphene and the conjugated polymer was also observed. These polymeric conjugated systems of modified graphene materials may open an interesting field for the application of graphene in photoelectric devices.

Novel synthesis of arylboronic acids by electroreduction of aromatic halides in the presence of trialkyl borates

A novel preparation of aryl and heteroarylboronic acids by an electrochemical coupling reaction is described. It is based on the reductive coupling between aromatic or heteroaromatic halides and a trialkyl borate. The reactions are carried out in DMF or THF with the use of sacrificial aluminium or magnesium anodes in a single-compartment cell. Arylboronic acids are obtained with moderate to good selectivities and isolated yields.