59239-47-3

Usage

Uses

Used in Pharmaceutical Research and Development:
((1E,3E)-4-phenylbuta-1,3-dien-1-yl)boronic acid is used as a key intermediate for the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical properties facilitate the development of new drugs with improved therapeutic profiles.
Used in Materials Science:
In the field of materials science, ((1E,3E)-4-phenylbuta-1,3-dien-1-yl)boronic acid is utilized as a component in the production of advanced materials such as liquid crystals and polymers, contributing to the creation of innovative products with specialized properties.
Used as a Reagent in Organic Reactions:
((1E,3E)-4-phenylbuta-1,3-dien-1-yl)boronic acid functions as a versatile reagent in a range of organic reactions. It is particularly valuable in processes like Suzuki-Miyaura coupling, olefination, and cross-coupling reactions, where it aids in the formation of carbon-carbon bonds, thereby expanding the scope of organic synthesis and drug discovery.

Downstream Products

• 1465-80-1 ethyl (E,E)-4-<4-phenylbuta-1,3-dien-1-yl>benzoate 
• 62695-68-5 (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one 
• 73414-54-7 3-methyl navenone-B 
• 82575-21-1 (E)-[(1E)-5,5,5-trifluoropenta-1,3-dien-1-yl]benzene 
• 3042-22-6 2-phenyl-1H-pyrrole 
• 172515-96-7 (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol 

Relevant academic research and scientific papers

Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates

Exchanging BF3 by CF3: The title reaction proceeds under exceedingly mild reaction conditions and provides 2-arylvinyl- and 2-heteroarylvinyl-substituted substrates with E/Z selectivities of more than 95:5. Experimental observations suggest that the reaction does not proceed through a transmetalation of the RBF3K species to the iron catalyst. Copyright

Lithium bis(ethylenedioxyboryl)methide and its reactions with carbonyl compounds and with the chlorotriphenyl derivatives of germanium, tin and lead

Transesterification of tris(dimethoxyboryl)methane, HC[B(OCH3)2]3, with ethylene glycol yielded tris(ethylenedioxyboryl)methane (I), HC(BO2C2H4)3 which with methyllithium in THF at -70°C precipitated lithium bis(ethylenedioxyboryl)methide (II), Li+ HC(BO2C2H4)2-. Reaction of II with Ph3MCl, where M = Ge, Sn, or Pb, gave Ph3MCH(BO2C2H4)2. The analogous 1,3-propanediol ester, Li+HC(BO2C3H6)2-, yielded Ph3MCH(BO2C3H6)2. Treatment of Ph3SnCH(BO2C2H4)2 with MeLi followed by Ph3SnCl gave (Ph3Sn)2CHBO2C2H4, showing that one B and one Sn atom are sufficient to stabilize a carbanion. Reaction of II with aldehydes gave high yields of 1-alkene-1-boronic esters, RCHCHBO2C2H4, with unexpectedly high stereoselectivity, 90-100% trans by NMR analysis. Aqueous work-up of these boronic esters yielded the boronic acids, RCHCHB (OH)2, which crystallized as the pure trans isomers. Ketones react with II in an analogous manner. The reaction with acetophenone was not stereospecific. Functional group compatibility has been demonstrated in condensations of II with 1,3-dichloroacetone, cinnamaldehyde, p-nitrobenzaldehyde, and p-dimethylaminobenzaldehyde. The trans geometry of the major isomer of CH3CHCHBO2C2H4 was proved by B-butylation with butyllithium followed by rearrangement with iodine and base to form cis-2-heptene, a sequence of known stereochemistry, and analogous structure proofs were carried out with cis-CH3CHCHBO2C2H4 and trans-C6H5CHCHBO2C2H4.