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| benzonitrile | |
|---|---|
| Name | Benzonitrile |
| IUPAC name | Benzonitrile |
| Other names | Phenylnitrile; Cyanobenzene |
| Formula | C7H5N |
| Molar mass | 103.12 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 1.01 g·cm−3 |
| Melting point | −13 °C |
| Boiling point | 191–192 °C |
| Solubility | Slightly soluble in water; miscible with organic solvents |
benzonitrile
Benzonitrile is an aromatic organic compound consisting of a phenyl ring bonded to a nitrile functional group. It is a colorless liquid historically encountered in laboratory and industrial settings and studied in contexts ranging from organic synthesis to astrochemistry. Benzonitrile's physical and spectroscopic properties have made it a subject of interest in analytical chemistry and molecular spectroscopy.
Benzonitrile has a planar Benzene-derived framework with a linear nitrile moiety attached to the ring, yielding the molecular formula C7H5N and a molecular mass of about 103.12 g·mol−1. Its electronic structure reflects conjugation between the Benzenoid ring and the C≡N triple bond, influencing dipole moment and UV–visible absorption; these features have been characterized using techniques developed at institutions such as Royal Institution and Max Planck Society. Crystallographic studies comparable to work at Cambridge University and ETH Zurich have resolved bond lengths and angles, while rotational spectroscopy investigations akin to those at NASA and Jet Propulsion Laboratory have detected benzonitrile in interstellar contexts. Physical data—melting point, boiling point, density—are routinely reported in handbooks compiled by organizations like IUPAC and American Chemical Society.
Laboratory preparation of benzonitrile commonly employs substitution reactions on aromatic precursors. Classical routes parallel methods pioneered by chemists associated with BASF and DuPont: dehydration of benzamide using reagents analogous to those from Sigma-Aldrich or conversion of aryl halides via palladium-catalyzed cyanation as in protocols influenced by work at University of Chicago and Harvard University. Industrial cyanation methods echo developments from Dow Chemical Company and often use metal-catalyzed cross-coupling employing catalysts similar to those developed at University of California, Berkeley and Massachusetts Institute of Technology. Alternative preparations include Sandmeyer-type transformations historically reported in journals tied to Royal Society of Chemistry and diazonium chemistry documented in reports from Max Planck Society groups.
Benzonitrile participates in reactions characteristic of both aromatic compounds and nitriles. Electrophilic aromatic substitution mechanisms mirror those explored in foundational studies at Imperial College London and École Polytechnique, while nucleophilic additions at the nitrile carbon follow paradigms elaborated by researchers at California Institute of Technology and Stanford University. Reduction to benzylamine employs catalytic hydrogenation techniques developed for processes at Shell plc and Linde plc, while hydrolysis to benzoic acid proceeds under acidic or basic conditions discussed in literature from University of Cambridge and Yale University. Metal coordination chemistry with transition metals has been investigated in laboratories such as ETH Zurich and Max Planck Institute for Chemical Energy Conversion, where benzonitrile acts as a ligand in complexes analogous to those reported for carbon monoxide and phosphines.
Benzonitrile serves as a solvent and synthetic intermediate in organic synthesis pipelines used by companies like Bayer and Siemens; it features in protocols for pharmaceutical intermediates studied at Pfizer and Merck & Co.. It is employed as a ligand surrogate in coordination chemistry research at institutions including University of Oxford and Columbia University, and as a model compound in spectroscopic studies relevant to observatories such as ALMA and Green Bank Observatory. In materials science, benzonitrile derivatives appear in design work at Bell Labs and research groups at Tokyo Institute of Technology for organic electronic precursors. Its detection in interstellar medium research has linked bench chemistry to astrophysical studies at Harvard–Smithsonian Center for Astrophysics and Max Planck Institute for Radio Astronomy.
Toxicological profiles compiled by agencies like Occupational Safety and Health Administration and European Chemicals Agency indicate that benzonitrile is harmful if inhaled or ingested and can cause irritation of eyes and respiratory tract; exposure controls follow standards set by National Institute for Occupational Safety and Health and World Health Organization. Acute toxicity is related to potential cyanide release under extreme conditions, a hazard noted in emergency response guidance from Federal Emergency Management Agency and United States Environmental Protection Agency. Handling precautions align with laboratory practice guidelines promulgated by Centers for Disease Control and Prevention and institutional safety offices at universities such as Johns Hopkins University.
Environmental monitoring programs run by agencies like United States Environmental Protection Agency and Environment Canada assess volatility and biodegradation pathways; benzonitrile exhibits low aqueous solubility and moderate persistence in soil and air under conditions reported in studies from University of Toronto and University of Melbourne. Atmospheric chemistry involving reaction with radicals has been modeled in climate and air-quality studies associated with NASA and European Space Agency, while biodegradation and microbial metabolism have been explored in research linked to Woods Hole Oceanographic Institution and Scripps Institution of Oceanography. Occupational and community exposure assessments follow frameworks developed by National Institute for Occupational Safety and Health and European Food Safety Authority.
Category:Organic nitriles