167693-07-4

Basic information

• Product Name: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-phenylbutyl)-
• Synonyms: 1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-(4-phenylbutyl);D-1413;2-(4-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butane
• CAS NO: 167693-07-4
• Molecular Formula: C16H25BO2
• Molecular Weight: 260.184
• Mol File: 167693-07-4.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-phenylbutyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-phenylbutyl)-(167693-07-4)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-phenylbutyl)-(167693-07-4)

Safety Data

• Hazardous Substances Data: 167693-07-4(Hazardous Substances Data)

Upstream product

• 768-56-9 4-Phenylbut-1-ene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 16520-62-0 4-Phenyl-1-butyne 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 73183-34-3 bis(pinacol)diborane 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 74-97-5 chlorobromomethane 
• 329685-40-7 4,4,5,5-tetramethyl-2-(3-phenylpropyl)-[1,3,2]dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 1570511-19-1 2,2'-(4-phenylbutane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 2270-20-4 5-Phenylpentanoic acid 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 122-97-4 3-Phenyl-1-propanol 

Downstream Products

• 36329-86-9 (4-phenylbutyl)boronic acid 
• 36884-28-3 5-phenyl-1-pentanal 
• 10521-91-2 5-phenylpentan-1-ol 
• 20620-59-1 5-phenyl-n-valeric acid methyl ester 
• 3360-41-6 4-phenyl-butan-1-ol 

Relevant articles and documents

Synthesis of DBpin using Earth-abundant metal catalysis

The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.

Selective hydroboration of equilibrating allylic azides

The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.

Enantioselective Cobalt-Catalyzed Cascade Hydrosilylation and Hydroboration of Alkynes to Access Enantioenriched 1,1-Silylboryl Alkanes

Enantioenriched 1,1-silylboryl alkanes possess silyl and boryl groups that are both connected to the same stereogenic carbon center at well-defined orientations. As these chiral multifunctionalized compounds potentially offer two synthetic handles, they are highly valued building blocks in asymmetric synthesis as well as medicinal chemistry. Despite the potential usefulness, efficient synthetic approaches for their preparation are scarce. Seeking to address this deficiency, an enantioselective cobalt-catalyzed hydrosilylation/hydroboration cascade of terminal alkynes has been realized. This protocol constitutes an impressive case of chemo-, regio-, and stereoselectivity wherein the two different hydrofunctionalization events are exquisitely controlled by a single set of metal catalyst and ligand, an operation which would usually require two separate catalytic systems. Downstream transformations of enantioenriched 1,1-silyboryl alkanes led to various valuable chiral compounds. Mechanistic studies suggest that the present reaction undergoes highly regioselective and stereocontrolled sequential hydrosilylation and hydroboration processes.