223799-24-4

Basic information

• Product Name: 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane
• Synonyms: 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane
• CAS NO: 223799-24-4
• Molecular Weight: 204.077
• Mol File: 223799-24-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane(223799-24-4)
• EPA Substance Registry System: 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane(223799-24-4)

Safety Data

• Hazardous Substances Data: 223799-24-4(Hazardous Substances Data)

Usage

Type of compound

Boron-containing heterocyclic compound

Usage

Commonly used in organic synthesis and medicinal chemistry

Ability

Valued for its ability to form carbon-carbon bonds

Reagent

Often used in Suzuki-Miyaura coupling reactions

Building block

Used in the synthesis of pharmaceuticals and agrochemicals

Reaction conditions

Mild reaction conditions

Functional group tolerance

High functional group tolerance, making it a versatile tool for the construction of complex organic molecules.

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 5097-06-3 3,3'-sulfinylbis(methylbenzene) 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 28987-79-3 m-tolylmagnesium bromide 
• 4250-47-9 (3-CH₃-C₆H₄)BCl₂ 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 17933-03-8 m-tolylboronic acid 
• 3955-72-4 3-methylphenyl tosylate 
• 1077-02-7 3-methylphenyl methanesulfonate 

Downstream Products

• 1060639-06-6 1,4,5,8-tetrakis(3-methylphenyl)-9,10-anthracenedione 
• 1313442-54-4 C₂₄H₂₉NO₂ 
• 14625-58-2 2-(3-methylphenyl)benzoxazole 
• 1334512-04-7 C₁₆H₁₆ 
• 1334512-28-5 (S)-3-(3-methylphenyl)-3-phenyl-1-butene 
• 1334512-32-1 (S)-3-(3-methylphenyl)-3-phenyl-1-butanol 
• 1329491-64-6 2-[(3'-methylbiphenyl-2-yl)sulfinyl]pyridine 
• 643-93-6 3-methylbiphenyl 
• 1356399-82-0 1-(3-methylphenyl)-1-(naphthalen-2-yl)ethanol 
• 198648-99-6 tert-butyl 4-hydroxy-4-(3-methylphenyl)-1-piperidinecarboxylate 
• 6957-08-0 1-(m-Methylphenyl)cyclohexanol 
• 1510828-54-2 2-phenyl-6-(m-tolyl)pyridine 
• 4373-61-9 2-(m-tolyl)pyridine 
• 1594124-08-9 (S)-2-((3-methoxyphenyl)(m-tolyl)methyl)-5,5-dimethyl-1,3,2-dioxaborinane 

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.

Palladium-catalysed reactions of conjugated enyne oxiranes with organoborons: A diastereoselective method of the synthesis of 2,4,5-trienol derivatives

A palladium-catalysed reaction of conjugated enyne oxiranes with organoboron reagents is described. This method allows aryl-substituted vinylallenes containing a hydroxyl group on the allylic position to be synthesized, with good diastereomeric ratios, un

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