214360-70-0

Basic information

• Product Name: Thiophene-3-boronic acid pinacol ester
• Synonyms: 3-THIOPHENEBORONIC ACID, PINACOL ESTER;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)THIOPHENE;THIOPHENE-3-BORONIC ACID, PINACOL ESTER;4,4,5,5-Tetramethyl-2-thiophen-3-yl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(thien-3-yl)-1,3,2-dioxaborolane;4,4,5,5-TetraMethyl-2-(3-thienyl)-1,3,2-dioxaborolane;Thiophene-3-boronic acid pinacal ester;Thiophene-3-boronic acid pinacal este
• CAS NO: 214360-70-0
• Molecular Formula: C₁₀H₁₅BO₂S
• Molecular Weight: 210.1
• Product Categories: Boronic acids
• Mol File: 214360-70-0.mol
• Article Data: 43

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 286.547 °C at 760 mmHg
• Flash Point: 127.099 °C
• Appearance: /
• Density: 1.075 g/cm³
• Vapor Pressure: 0.00452mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: Thiophene-3-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene-3-boronic acid pinacol ester(214360-70-0)
• EPA Substance Registry System: Thiophene-3-boronic acid pinacol ester(214360-70-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• TSCA: No
• Hazardous Substances Data: 214360-70-0(Hazardous Substances Data)

Usage

General Description

Thiophene-3-boronic acid pinacol ester is a chemical compound used extensively as a reagent in palladium-catalyzed cross-coupling reactions and in organic synthesis. It's a derivative of boronic acid, structured with a thiophene ring, and it's often employed in Suzuki coupling, which is a powerful tool for constructing carbon-carbon bonds. Due to its reactive properties, this compound is particularly useful in the synthesis of complex organic molecules, including pharmaceuticals and polymers. It is generally available as a white to light-brown powder and should be handled with care due to its potential to cause skin and eye irritation.

InChI:InChI=1/C10H15BO2S/c1-9(2)10(3,4)13-11(12-9)8-5-6-14-7-8/h5-7H,1-4H3

Upstream product

• 872-31-1 3-Bromothiophene 
• 73183-34-3 bis(pinacol)diborane 
• 17249-80-8 3-chlorothiophene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 88-13-1 3-Thiophene carboxylic acid 
• 188290-36-0 thiophene 
• 6165-69-1 Thien-3-ylboronic acid 
• 616-44-4 3-Methylthiophene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 10486-61-0 3-thienyl iodide 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 

Downstream Products

• 91720-80-8 3-(1-phenylethyl)thiophene 
• 937602-39-6 5-nitro-2-(thiophen-3-yl)pyridine 
• 16938-72-0 3-(m-tolyl)thiophene 
• 56421-82-0 5-methyl-2-(thiophen-3-yl)pyridine 
• 21298-55-5 3-(2-pyridyl)thiophene 
• 65016-62-8 3-octylthiophene 

Relevant articles and documents

Selective Placement of Bromide and Pinacolboronate Groups about a Tellurophene: New Building Blocks for Optoelectronic Applications

Selective protodeboronation of preformed phosphorescent di- and tetrapinacolboronate (BPin)-substituted tellurophenes controllably affords new tellurophene products that show photoluminescence or, in the case of tellurophenes lacking BPin groups at the 2,5-positions, nonemissive behavior; for comparison the protodeboronation of select thiophene and selenophenes is also reported. The resulting BPin-appended tellurophenes are promising candidates for postfunctionalization via Suzuki-Miyaura cross-coupling and can be effectively converted into their respective brominated tellurophene counterparts via treatment with excess CuBr2. It is expected from prior studies that these brominated tellurophenes will be suitable building blocks (and monomers) for the preparation of conjugated oligomers and polymers featuring narrower optical band gaps in relation to their lighter chalcogen analogues; in this regard preliminary Stille coupling chemistry is reported.

Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane

A benzoic acid-promoted C2-H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.