In 2019,Organometallics included an article by Eberhardt, Nathan A.; Wellala, Nadeesha P. N.; Li, Yingze; Krause, Jeanette A.; Guan, Hairong. Safety of (4-Bromophenyl)methanol. The article was titled 《Dehydrogenative Coupling of Aldehydes with Alcohols Catalyzed by a Nickel Hydride Complex》. The information in the text is summarized as follows:
A nickel hydride complex, {2,6-(iPr2PO)2C6H3}NiH, has been shown to catalyze the coupling of RCHO and R’OH to yield RCO2R’ and RCH2OH, where the aldehyde also acts as a hydrogen acceptor and the alc. also serves as the solvent. Functional groups tolerated by this catalytic system include CF3, NO2, Cl, Br, NHCOMe, and NMe2, whereas phenol-containing compounds are not viable substrates or solvents. The dehydrogenative coupling reaction can alternatively be catalyzed by an air-stable nickel chloride complex, {2,6-(iPr2PO)2C6H3}NiCl, in conjunction with NaOMe. Acids in unpurified aldehydes react with the hydride to form nickel carboxylate complexes, which are catalytically inactive. Water, if present in a significant quantity, decreases the catalytic efficiency by forming {2,6-(iPr2PO)2C6H3}NiOH, which causes catalyst degradation On the other hand, in the presence of a drying agent, {2,6-(iPr2PO)2C6H3}NiOH generated in situ from {2,6-(iPr2PO)2C6H3}NiCl and NaOH can be converted to an alkoxide species, becoming catalytically competent. The proposed catalytic mechanism features aldehyde insertion into the nickel hydride as well as into a nickel alkoxide intermediate, both of which have been exptl. observed Several mechanistically relevant nickel species including {2,6-(iPr2PO)2C6H3}NiOC(O)Ph, {2,6-(iPr2PO)2C6H3}NiOPh, and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh have been independently synthesized, crystallog. characterized, and tested for the catalytic reaction. While phenol-containing mols. cannot be used as substrates or solvents, both {2,6-(iPr2PO)2C6H3}NiOPh and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh are efficient in catalyzing the dehydrogenative coupling of PhCHO with EtOH. The experimental part of the paper was very detailed, including the reaction process of (4-Bromophenyl)methanol(cas: 873-75-6Safety of (4-Bromophenyl)methanol)
(4-Bromophenyl)methanol(cas: 873-75-6) undergoes three-component reaction with acetylferrocene and arylboronic acid to give ferrocenyl ketones containing biaryls.Safety of (4-Bromophenyl)methanol It is used in the synthesis of amphiphilic, symmetric rod-coil, triblock copolymer of poly(9,9-didodecylfluorene-2,7-diyl) and poly(hydroxyl ethyl methacrylate)
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts