Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane
[CAS# 78782-17-9]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane
• Synonyms: Bis((pinacolato)boryl)methane
• Molecular Formula: C₁₃H₂₆B₂O₄
• Molecular Weight: 267.97
• CAS Registry Number: 78782-17-9
• EC Number: 810-358-7
• SMILES: B1(OC(C(O1)(C)C)(C)C)CB2OC(C(O2)(C)C)(C)C

Properties

• Density: 0.97±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 272.0±23.0 ºC (760 Torr), Calc.^*
• Flash point: 118.3±22.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane, often referred to as bis(pinacolato)diboron (BPin), is a notable organoboron compound with significant applications in organic synthesis. The compound is characterized by its two boron atoms, each bonded to a pinacolato ligand, and a central methane unit connecting these two boron centers. Its discovery and diverse applications underscore its importance in modern chemical research and industrial processes.

The discovery of bis(pinacolato)diboron dates back to the early 1970s when it was first synthesized and reported in the chemical literature. The compound was developed as part of ongoing research into boron-based reagents and their potential applications in organic chemistry. The synthesis of bis(pinacolato)diboron was achieved by the reaction of boron trifluoride etherate with pinacol, leading to the formation of this versatile reagent. This development was a significant milestone in the field of organoboron chemistry, paving the way for new methodologies and applications.

Bis(pinacolato)diboron is primarily used as a reagent in various organic transformations, particularly in the fields of synthetic organic chemistry and medicinal chemistry. One of its key applications is in the Suzuki-Miyaura cross-coupling reaction, a widely used method for forming carbon-carbon bonds. In this reaction, bis(pinacolato)diboron serves as a boron source that reacts with aryl or vinyl halides in the presence of a palladium catalyst to form biaryl or diaryl compounds. This reaction is crucial for the synthesis of a wide range of complex organic molecules, including pharmaceuticals, agrochemicals, and materials.

The compound is also utilized in the development of new synthetic methodologies. Its ability to form stable organoboron intermediates makes it valuable for designing and optimizing reactions that involve boron chemistry. For example, bis(pinacolato)diboron is employed in the synthesis of boronic acids and esters, which are important building blocks in organic synthesis. These boronic derivatives are used in a variety of chemical transformations and are essential for creating complex molecules with precise functional groups.

In addition to its applications in organic synthesis, bis(pinacolato)diboron has found use in materials science. It is used in the development of boron-containing polymers and materials with unique electronic and optical properties. The incorporation of boron into polymer matrices can enhance their mechanical and thermal properties, making them suitable for various industrial applications, including electronics and advanced materials.

Furthermore, bis(pinacolato)diboron has been explored for its potential applications in environmental and medicinal chemistry. Its role as a reagent in the synthesis of bioactive compounds and its involvement in the design of new materials with environmental applications highlight its versatility and significance in these fields.

Overall, bis(pinacolato)diboron represents a significant advancement in organoboron chemistry with a range of applications that impact various scientific and industrial domains. Its discovery has contributed to the development of new synthetic methods and materials, demonstrating its importance in advancing both fundamental and applied chemical research.