Tributyl borate
[CAS# 688-74-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Borate
• Name: Tributyl borate
• Synonyms: Tributoxyborane
• Molecular Formula: C₁₂H₂₇BO₃
• Molecular Weight: 230.15
• CAS Registry Number: 688-74-4
• EC Number: 211-706-5
• SMILES: B(OCCCC)(OCCCC)OCCCC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.853 g/mL
• Melting point: -70 ºC
• Index of Refraction: 1.410, Calc.^*, 10409
• Boiling Point: 230.6±8.0 ºC (760 mmHg), Calc.^*, 230-235 ºC
• Flash Point: 93.3±0.0 ºC, Calc.^*, 93 ºC
• Water solubility: decomposes

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Hazard Statements: H302-H312-H315-H318-H319-H335-H360FD
• Precautionary Statements: P203-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Reproductive toxicity	Repr.	1B	H360FD

Discovory and Applicatios

Tributyl borate (TBB) is an organoboron compound with the chemical formula C12H27BO4. It is classified as a trialkyl borate and is characterized by the presence of three butyl groups attached to a boron atom. TBB is a colorless, viscous liquid known for its solubility in organic solvents and its ability to form stable complexes with various substrates.

The discovery of tributyl borate can be traced back to the early 20th century when researchers began exploring the chemical properties and applications of organoboron compounds. One of the pioneering works in this area was conducted by chemist Charles A. Coates in the 1940s, who studied various trialkyl borates, including tributyl borate. His research highlighted the potential of these compounds in organic synthesis, leading to further investigations into their reactivity and applications.

Tributyl borate has gained recognition for its diverse applications in various fields, particularly in organic chemistry and materials science. One of its primary uses is as a reagent in organic synthesis, where it serves as a boron source in various chemical reactions. TBB is often employed in the synthesis of organoboron compounds, which are valuable intermediates in the production of pharmaceuticals, agrochemicals, and fine chemicals. Its ability to facilitate the formation of carbon-boron bonds has made it an essential tool for chemists working in synthetic organic chemistry.

In addition to its role in organic synthesis, tributyl borate is utilized as a solvent and reaction medium in various chemical processes. Its high boiling point and low volatility make it suitable for use in high-temperature reactions and as a reaction solvent for polymerization processes. TBB is also employed in the preparation of boron-containing polymers, which exhibit unique properties such as improved thermal stability and chemical resistance. These materials have applications in coatings, adhesives, and other industrial products.

Moreover, tributyl borate has found applications in the field of analytical chemistry. It is often used as a derivatizing agent for the analysis of alcohols and phenols, enhancing their detectability in chromatographic techniques such as gas chromatography (GC) and high-performance liquid chromatography (HPLC). The ability of TBB to form stable complexes with various analytes improves the sensitivity and selectivity of these analytical methods, making it a valuable reagent in chemical analysis.

Another important application of tributyl borate is in the formulation of lubricants and plasticizers. Its compatibility with various polymer matrices allows it to enhance the performance of lubricants by providing excellent lubricating properties and reducing friction. Additionally, TBB serves as a plasticizer in polymer formulations, improving the flexibility and processability of materials used in packaging, automotive parts, and consumer products.

Despite its many beneficial applications, safety considerations are crucial when handling tributyl borate. It is classified as a hazardous substance, and exposure may lead to skin and eye irritation. Therefore, appropriate safety measures, including the use of personal protective equipment and proper ventilation, should be implemented when working with this compound.

In summary, tributyl borate is a versatile organoboron compound with a wide range of applications in organic synthesis, materials science, and analytical chemistry. Its discovery has paved the way for advancements in various chemical processes and products, contributing significantly to the fields of chemistry and industry.

References

2020. Fabrication of B-Containing Glass and Glass-Ceramic Materials via Liquid Organic Phase Pyrolysis. Russian Journal of Inorganic Chemistry, 65(3).
DOI: 10.1134/s0036023620030055

1959. Preparation of trialkylborines by the action of organometallic compounds on metaboric esters. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 8(6).
DOI: 10.1007/bf00916686

2023. Effectively improving flame retardancy levels of finished cotton fabrics only by simple binary silicon-boron oxide sols. Journal of Polymer Research, 30(11).
DOI: 10.1007/s10965-023-03812-5