568572-21-4

Basic information

• Product Name: 1,3,2-Dioxaborinane, 2-benzo[b]thien-2-yl-5,5-dimethyl-
• CAS NO: 568572-21-4
• Molecular Formula: C13H15BO2S
• Molecular Weight: 246.138
• Mol File: 568572-21-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborinane, 2-benzo[b]thien-2-yl-5,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborinane, 2-benzo[b]thien-2-yl-5,5-dimethyl-(568572-21-4)
• EPA Substance Registry System: 1,3,2-Dioxaborinane, 2-benzo[b]thien-2-yl-5,5-dimethyl-(568572-21-4)

Safety Data

• Hazardous Substances Data: 568572-21-4(Hazardous Substances Data)

Usage

Chemical compound

A substance with a unique molecular structure consisting of a boron-containing heterocyclic ring with a benzo[b]thiophene group attached to it.

Building block

Commonly used in organic synthesis and medicinal chemistry as a building block for creating more complex molecules.

Potential applications

Has potential applications in the development of pharmaceuticals and agrochemicals due to its ability to participate in various chemical reactions and form important chemical bonds.

Unique structure and reactivity

Its unique structure and reactivity make it an important reagent for the synthesis of complex organic molecules.

Lewis acid catalyst

The boron atom in the molecule can act as a Lewis acid catalyst, further expanding its usefulness in chemical processes.

Chemical reactions

Capable of participating in various chemical reactions, such as cross-coupling reactions, Suzuki-Miyaura reactions, and other C-C and C-heteroatom bond-forming reactions.

Stability

Relatively stable under a range of reaction conditions, making it suitable for use in various synthetic applications.

Solubility

Generally soluble in common organic solvents, such as tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), and dichloromethane (DCM), which facilitates its use in chemical reactions.

Purity

Often available in high purity, which is essential for its use in sensitive chemical reactions and the synthesis of pharmaceutical compounds.

Safety and handling

As with any chemical compound, proper safety precautions should be taken when handling 1,3,2-Dioxaborinane, 2-benzo[b]thien-2-yl-5,5-dimethyl-, including the use of appropriate personal protective equipment (PPE) and following established safety guidelines.

Upstream product

• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 6314-28-9 benzo[b]thiophene-2-carboxylic acid 
• 38210-35-4 2-(benzothiophen-2-yl)pyridine 
• 22913-24-2 methyl benzo[b]thiophene-2-carboxylate 

Relevant articles and documents

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.

Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters

(Chemical Equation Presented) The copper(I)-catalyzed carboxylation reaction of aryl- and alkenylboronic esters proceeded smoothly under CO 2 to give the corresponding carboxylic acid in good yield. This reaction showed wide generality with higher functional group tolerance compared to the corresponding Rh(I)-catalyzed reaction.