4406-77-3

Basic information

• Product Name: 2-PHENYL-1,3,2-DIOXABORINANE
• Synonyms: 2-PHENYL-1,3,2-DIOXABORINANE;Phenylboronic acid 1,3-propanediol ester, 99%;2-Phenyl-1,3,2-dioxaborinane, Phenyl boronic acid glycol ester;2-Phenyl-1,3-dioxa-2-boracyclohexane;2-Phenyl-2-bora-1,3-dioxane;2-Phenyl-5,6-dihydro-4H-1,3,2-dioxaborin;2-Phenyldihydro-4H-1,3,2-dioxaborin;3-propanediol ester
• CAS NO: 4406-77-3
• Molecular Formula: C₉H₁₁BO₂
• Molecular Weight: 161.99
• Mol File: 4406-77-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 106 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.077 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00648mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-PHENYL-1,3,2-DIOXABORINANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-1,3,2-DIOXABORINANE(4406-77-3)
• EPA Substance Registry System: 2-PHENYL-1,3,2-DIOXABORINANE(4406-77-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4406-77-3(Hazardous Substances Data)

Usage

General Description

2-PHENYL-1,3,2-DIOXABORINANE is a chemical compound with the molecular formula C8H11BO2. It is a boron-containing heterocyclic compound that is derived from boron and various alcohols. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Its unique structure makes it useful in a variety of reactions, including Suzuki-Miyaura cross-coupling reactions and other organic transformations. 2-PHENYL-1,3,2-DIOXABORINANE has also been studied for its potential applications in pharmaceuticals and materials science due to its versatile reactivity and stability.

InChI:InChI=1/C9H11BO2/c1-2-5-9(6-3-1)10-11-7-4-8-12-10/h1-3,5-6H,4,7-8H2

Upstream product

• 504-63-2 trimethyleneglycol 
• 98-80-6 phenylboronic acid 
• 1061181-00-7 (-)-4,5-dimethyl-2-phenyl[1.3.2]dioxaborolane 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 6638-70-6 (3aR,7aS)-2-phenyl-hexahydro-2H-1,3,2-benzodioxaborole 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 2848-16-0 diphenyldiboronic acid 
• 3262-89-3 triphenylboroxine 

Downstream Products

• 171288-08-7 6-phenyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 42353-94-6 (E)-oct-4-en-4-ylbenzene 
• 92-52-4 biphenyl 
• 941-69-5 N-phenyl-maleimide 
• 6914-98-3 2-phenylbenzo[de]isoquinoline-1,3-dione 
• 2550-26-7 4-Phenyl-2-butanone 
• 613-37-6 4-methoxylbiphenyl 
• 219967-87-0 tricarbonylrhenium(η(5)-C5H4C6H5) 
• 3076-54-8 phenyllead(IV) triacetate 
• 97782-90-6 tert-butylphenyl(3-hydroxypropoxy)borane 
• 889649-63-2 cis-C₆H₅BO₂(CH₂)3O₂Pd(PPh₃)2 
• 108-88-3 toluene 
• 62787-21-7 3,5-di-tert-butylphenyl phenyl ether 
• 58-72-0 Triphenylethylene 

Relevant articles and documents

Double-Stranded Helical Oligomers Covalently Bridged by Rotary Cyclic Boronate Esters

Novel double helices covalently bridged by cyclic boronate esters were synthesized from complementary dimers with an m-terphenyl backbone joined by a chiral or achiral phenylene linker bearing diethyl boronates and diols, respectively. The X-ray crystallographic analysis and variable-temperature NMR and circular dichroism measurements, along with theoretical calculations, revealed that the double helices function as a “molecular rotor” in which the cyclic boronate ester units rotate, yielding two stable rotamers at low temperatures. Moreover, our data indicates that the covalently bonded double helices can undergo a unique helix-inversion simultaneously with a rotational motion of the boronate esters.

Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement

It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement. Copyright

NOVEL BORATE DERIVATIVES AND THEIR APPLICATIONS

Borates, compositions comprising chiral (cyclic and acyclic) and achiral (cyclic and acyclic) borates; chiral (cyclic and acyclic) and achiral (cyclic and acyclic) biborates; and methods for their synthesis. Additionally, a significantly improved synthetic protocol for the synthesis of wide range of boronates starting from borates or biborates and Grignard or organolithium reagents that can be used for kilo lab and commercial scale production.