905966-46-3

Basic information

• Product Name: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-(3-thienyl)-
• CAS NO: 905966-46-3
• Molecular Formula: C9H13BO2S
• Molecular Weight: 196.078
• Mol File: 905966-46-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-(3-thienyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-(3-thienyl)-(905966-46-3)
• EPA Substance Registry System: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-(3-thienyl)-(905966-46-3)

Safety Data

• Hazardous Substances Data: 905966-46-3(Hazardous Substances Data)

Usage

Structure

Boronic acid derivative with a dioxaborinane ring and a thienyl group

Organic synthesis

Used as a reagent for cross-coupling reactions

Suzuki-Miyaura coupling

Particularly effective in this type of reaction

Pharmaceutical synthesis

Utilized in the synthesis of various pharmaceuticals

Agrochemical synthesis

Employed in the production of agrochemicals

Materials science

Studied for potential applications in organic electronic materials and sensors

Functional groups

Boronic acid, dioxaborinane ring, and thienyl group

Reactivity

Active in cross-coupling reactions

Stability

Relatively stable under appropriate conditions

Solubility

Soluble in organic solvents, such as tetrahydrofuran (THF) or dimethyl sulfoxide (DMSO)

Appearance

Typically a solid or viscous liquid

Color

May vary depending on the specific compound and purity

Odor

May have a characteristic odor, but this can vary

Toxicity

Potentially toxic, depending on the specific compound and its concentration

Hazards

May be flammable or corrosive, depending on the compound

Storage

Should be stored in a cool, dry, and well-ventilated area, away from incompatible substances

Disposal

Follow proper waste disposal procedures and regulations for chemical compounds

Regulatory information

May be subject to specific regulations and guidelines depending on the region and intended use (e.g., REACH, TSCA)

Upstream product

• 872-31-1 3-Bromothiophene 
• 57186-57-9 2-methoxy-5,5,-dimethy-1,3,2-dioxaborinane 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 6165-69-1 Thien-3-ylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Downstream Products

• 20608-91-7 4-(thien-3-yl)benzoic acid methyl ester 
• 21308-81-6 3-(thiophen-3-yl)pyridine 
• 37784-63-7 ethyl-3 thiophene acetate 
• 2404-87-7 3-phenylthiophene 
• 1415045-62-3 N,N-diethyl-2-(thiophen-3-yl)benzamide 
• 1380226-50-5 N,N-dibenzylthienyl-3-amine 
• 133039-41-5 3-cinnamylthiophene 
• 1334512-05-8 C₁₃H₁₂S 
• 104934-52-3 3-dodecylthiophene 

Relevant articles and documents

Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates

A Ru0-catalyzed direct C-H arylation and alkenylation of furfural imines with aryl- or alkenyl-boronates, in the presence of benzylideneacetone as a sacrificial hydride acceptor, is disclosed. This reaction provides access, after hydrolysis, to C3-arylated or vinylated furfural derivatives, and thus valorizes these relevant building-blocks obtained from lignocellulosic biomass. This approach, involving C-H activation by a Ru0/RuII, cycle offers several advantages, notably simple, mild and neutral reaction conditions.

Selective Monoarylation of Aromatic Ketones and Esters via Cleavage of Aromatic Carbon-Heteroatom Bonds by Trialkylphosphine Ruthenium Catalysts

We report here the ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds. Under the newly developed catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and sty

Beyond Directed ortho Metalation: Ruthenium-Catalyzed Amide-Directed CAr-OMe Activation/Cross-Coupling Reaction of Naphthamides with Aryl Boronates

A new and general synthetic methodology for the construction of biaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzed cross-coupling of ortho-methoxy naphthamides with aryl boroneopentylates is described. The isomeric 1-MeO-2-naphthamides and 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamides in excellent yields. Competition experiments showed the higher reactivity of 1-MeO-2-naphthamide over 2-MeO-benzamide. Orthogonality between the C-O activation/cross-coupling and the Suzuki-Miyaura reactions was established. The method provides naphthalenes which are difficult to prepare by directed ortho metalation.