6783-04-6

Basic information

• Product Name: 1,3,2-Benzodioxaborole, 2-[(1E)-2-phenylethenyl]-
• Synonyms: (E)-styryl-1,3,2-benzodioxaborole;2-(2-phenylethenyl)-1,3,2-benzodioxaborole;(E)-1-styryl-1,3,2-benzodioxaborole;(E)-2-phenylethenylboronic acid catechol ester;trans-2-phenylethenyl-1,3,2-benzodioxaborole;(E)-styrylboronic acid catechol ester
• CAS NO: 6783-04-6
• Molecular Formula: C14H11BO2
• Molecular Weight: 222.051
• Mol File: 6783-04-6.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 1,3,2-Benzodioxaborole, 2-[(1E)-2-phenylethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Benzodioxaborole, 2-[(1E)-2-phenylethenyl]-(6783-04-6)
• EPA Substance Registry System: 1,3,2-Benzodioxaborole, 2-[(1E)-2-phenylethenyl]-(6783-04-6)

Safety Data

• Hazardous Substances Data: 6783-04-6(Hazardous Substances Data)

Usage

Chemical structure

A cyclic compound containing a boron, oxygen, and carbon atoms in a unique arrangement.

Common use

Widely used in organic synthesis and as a building block for various pharmaceutical compounds.

Reactivity

The presence of the boron atom gives this compound unique reactivity.

Applications

Useful in the development of new drugs and agrochemicals.

Aromatic structure

Contains a benzene ring and a dioxaborole moiety.

Medicinal chemistry

Potentially valuable for targeting specific biological receptors or enzymes.

Versatility

Has diverse applications in the field of organic chemistry and drug discovery.

Upstream product

• 536-74-3 phenylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 130407-46-4 mer-{(1,2-pentylenedioxy)boryl}(Cl)(PMe₃)3iridium hydride 
• 100-42-5 styrene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 10294-34-5 boron trichloride 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 39491-73-1 (E)-(4-methylpenta-1,3-dien-1-yl)benzene 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 103-26-4 Methyl cinnamate 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 270907-95-4 6-[(E)-styryl]-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 103-26-4 methyl cinnamate 
• 26071-86-3 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole 
• 215254-67-4 2,2'-(1-phenylethane-1,2-diyl)dibenzo[1,3,2]dioxaborole 
• 6502-98-3 5,5-dimethyl-3-[(E)-2-phenylvinyl]cyclohex-2-en-1-one 
• 1335044-43-3 [2-((E)-styryl)-4-methoxyphenyl]phosphonic acid diethyl ester 

Relevant articles and documents

XBphos-Rh: A halogen-bond assembled supramolecular catalyst

The use of halogen bonding as a tool to construct a catalyst backbone is reported. Specifically, pyridyl- and iodotetrafluoroaryl-substituted phosphines were assembled in the presence of a rhodium(i) precursor to form the corresponding halogen-bonded complex XBphos-Rh. The presence of fluorine substituents at the iodo-containing supramolecular motif was not necessary for halogen bonding to occur due to the template effect exerted by the rhodium center during formation of the halogen-bonded complex. The halogen-bonded supramolecular complexes were successfully tested in the catalytic hydroboration of terminal alkynes.

Synthesis and reaction chemistry of boryliridium hydride complexes formed by oxidative addition of catecholborane to iridium(I): Lessons for metal-catalyzed hydroboration

The mechanism of catalytic hydroboration was studied through the use of an iridium model complex. Oxidative addition of the B-H bond in (1,2-phenylenedioxy)borane (catecholborane) to (Me3P) 3Ir(COE)(Cl) (COE = cyclooctene) produces mer-(Me3P) 3Ir(Cl)(H)(BO2C6H4) (1). Compound 1 reacted with alkynes to form vinyliridium complexes and will catalyze the hydroboration of alkynes with (1,2-phenylenedioxy)borane. The mechanism of catalytic hydroboration of acetylenes with catecholborane involves: oxidative addition of the B-H bond to the iridium center, followed by chloride dissociation and acetylene coordination, migratory-insertion into the Ir-H bond to form the metallo-vinyl complex, and finally reductive elimination to produce trans-alkylvinylboronate esters. A stable metallo-vinyl complex was produced in the reaction of 1 with dimethylacetylene dicarboxylate and displayed two isomers in solution, one of which showed fluxional behavior. Single crystal X-ray diffraction elucidated a single solid-state structure, but the structures of the isomers in solution and the fluxional properties were studied with NMR spectroscopy and DFT calculations.

Catalytic hydroboration by an imido-hydrido complex of Mo(iv)

The imido-hydrido complex (ArN)Mo(H)(Cl)(PMe3)3 catalyses a variety of hydroboration reactions, including the first example of catalytic addition of HBCat to nitriles to form the bis(borylated) amines RCH2N(BCat)2/su