Bis(neopentyl glycolato)diboron
[CAS# 201733-56-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Boric acid
• Name: Bis(neopentyl glycolato)diboron
• Synonyms: 5,5,5',5'-Tetramethyl-2,2'-bi-1,3,2-dioxaborinane
• Molecular Formula: C₁₀H₂₀B₂O₄
• Molecular Weight: 225.89
• CAS Registry Number: 201733-56-4
• EC Number: 639-407-9
• SMILES: B1(OCC(CO1)(C)C)B2OCC(CO2)(C)C

Properties

• Melting point: 179-183 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Bis(neopentyl glycolato)diboron is a chemical compound with the formula C10H16B2O4, characterized by its two neopentyl glycolate ligands coordinated to a central diboron unit. This compound has attracted significant attention in recent years due to its unique structural features and its applications in various fields of chemistry.

The discovery of Bis(neopentyl glycolato)diboron arose from research focused on developing new boron-containing compounds with potential applications in organic synthesis and materials science. The compound is synthesized by reacting diboron compounds with neopentyl glycolate, a process that typically involves controlled conditions to ensure the formation of the desired product with high purity. This synthesis strategy leverages the reactivity of boron and the stability of neopentyl glycolate ligands to produce a compound with unique chemical properties.

One of the key applications of Bis(neopentyl glycolato)diboron is in organic synthesis, where it serves as a versatile reagent for the development of complex molecules. The compound is used in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for forming carbon-carbon bonds in organic chemistry. In this reaction, Bis(neopentyl glycolato)diboron acts as a boron source, facilitating the coupling of aryl and vinyl halides with various nucleophiles to form biaryl and polyaryl compounds. This application is particularly valuable for synthesizing pharmaceuticals, agrochemicals, and advanced materials.

In addition to its role in organic synthesis, Bis(neopentyl glycolato)diboron has applications in materials science. The compound is utilized in the development of new polymers and materials with tailored properties. Its boron-containing structure contributes to the formation of materials with specific electronic or optical characteristics, which can be exploited in fields such as organic electronics and photonics. The ability to incorporate boron into polymer matrices enables the creation of materials with enhanced stability and performance.

The compound also finds use in catalysis, where it serves as a catalyst or catalyst precursor in various chemical reactions. Its unique structure allows it to participate in catalytic processes, facilitating transformations that are difficult to achieve with other reagents. This aspect of its application broadens its utility in synthetic chemistry and materials development.

Overall, Bis(neopentyl glycolato)diboron represents a significant advancement in the field of boron chemistry. Its discovery and application in organic synthesis, materials science, and catalysis underscore its importance as a versatile and valuable compound in both research and industrial contexts.

References

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2018. PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation. *Synlett*.
DOI: 10.1055/s-0036-1591549

2015. Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acids. *Synthesis*.
DOI: 10.1055/s-0034-1378835

2015. Nickel-Catalyzed Ipso-Borylation of Aryl Methyl Ethers. *Synfacts*.
DOI: 10.1055/s-0034-1381121

2015. Borylation of Alkyl Bromides by Using Copper(I) Oxide Nanoparticles on Carbon Black. *Synfacts*.
DOI: 10.1055/s-0035-1560135