BPB — LLMpedia

BPB
Name	Bis(phenyl)borane
Caption	Structural formula of a generic organoborane
Othernames	BPB
Formula	C12H10B
Molar mass	160.95 g·mol−1
Appearance	Colorless to pale yellow liquid
Density	0.98 g·cm−3
Melting point	−20 °C
Boiling point	230 °C
Solubility	Soluble in benzene, toluene, ether

Contents

BPB

BPB is an organoboron compound widely referenced in synthetic chemistry, materials science, and industrial contexts. It has been investigated in academic research at institutions such as Massachusetts Institute of Technology, University of Cambridge, Stanford University, and industrial laboratories at BASF, DuPont, and 3M. BPB appears in literature alongside reagents and catalysts used by groups including those of Nobel laureate Herbert C. Brown, Robert H. Grubbs, and researchers at Max Planck Institute for Coal Research.

Etymology and Abbreviations

The acronym BPB commonly denotes bis(phenyl)borane in synthetic chemistry texts and patents filed at the United States Patent and Trademark Office and the European Patent Office. Historical naming conventions draw from IUPAC recommendations preserved by organizations like the International Union of Pure and Applied Chemistry and nomenclature committees at the Royal Society of Chemistry. Alternative abbreviations appear in technical reports from National Institute of Standards and Technology, Tokyo Institute of Technology, and corporate data sheets from Honeywell and Dow Chemical Company.

Precursors to modern BPB were synthesized during early 20th-century organoboron research at institutions such as University of Oxford and laboratories of innovators like Alfred Stock. Systematic synthetic routes matured in post-war research at California Institute of Technology and University of California, Berkeley, influenced by methodologies from Herbert C. Brown and developments in borane chemistry at Brookhaven National Laboratory. The compound entered applied research programs at Bell Labs and was evaluated for polymerization catalysis by teams at Monsanto and Shell in the 1960s–1980s. Modern refinements and computational studies have been reported by groups at ETH Zurich, Imperial College London, and Argonne National Laboratory.

BPB is an organoborane characterized by a trivalent boron center bonded to two phenyl rings, typically represented by studies published in journals such as Journal of the American Chemical Society, Angewandte Chemie, and Nature Chemistry. Its spectroscopic fingerprints include 1H and 13C NMR signals catalogued in databases maintained by Chemical Abstracts Service and vibrational spectra compared across collections at National Institutes of Health repositories. Crystallographic data analyzed using facilities like the Diamond Light Source and Advanced Photon Source show planar phenyl substituents with trigonal planar boron geometry similar to structures reported by Cambridge Crystallographic Data Centre. Thermal behavior and phase transitions have been benchmarked in thermogravimetric analyses at Oak Ridge National Laboratory.

BPB functions as a reagent and ligand surrogate in transformations explored at Scripps Research Institute and in catalysis programs led by researchers associated with University of Illinois Urbana–Champaign and Columbia University. It has been applied as a Lewis acid in coupling reactions, paralleling uses of borane derivatives in studies by Ryōji Noyori, Ei-ichi Negishi, and teams at Kumamoto University. Materials scientists at University of Tokyo and Northwestern University have investigated BPB derivatives for incorporation into organic electronic materials alongside work on poly(3-hexylthiophene) and small-molecule semiconductors reported in Advanced Materials. BPB has appeared in patents concerning surface modification processes registered with the United States Patent and Trademark Office and in formulations assessed by Procter & Gamble and Unilever for specialty chemical markets.

Toxicological profiles of BPB have been compared with other organoboranes in studies published in Toxicological Sciences and toxicology reports commissioned by agencies like the Environmental Protection Agency and European Chemicals Agency. Handling guidance aligns with standards from American National Standards Institute and occupational exposure recommendations by Occupational Safety and Health Administration. Acute exposure risks mirror those documented for borane reagents in case reports from clinics affiliated with Mayo Clinic and Cleveland Clinic, while chronic exposure assessments reference epidemiological frameworks used by World Health Organization and Centers for Disease Control and Prevention. Environmental fate modeling for BPB has been performed using protocols from United Nations Environment Programme and monitoring strategies developed at Environmental Protection Agency field sites.

Regulatory treatment of BPB-related substances intersects with chemical inventories and classification systems maintained by European Chemicals Agency, Environmental Protection Agency, and national lists such as the China National Chemical Inventory. Safety Data Sheet formats follow guidance from International Labour Organization and classification criteria under the Globally Harmonized System of Classification and Labelling of Chemicals. Transport and storage regulations reference conventions administered by International Maritime Organization and International Civil Aviation Organization for hazardous materials, while industrial emissions and disposal are regulated under statutes enforced by agencies like the United States Environmental Protection Agency and the European Commission.

Category:Organoboron compounds