15961-35-0

Basic information

• Product Name: 4,4,6-TRIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE
• Synonyms: PHENYLBORONIC ACID, HEXYLENE GLYCOL CYCLIC ESTER;4,4,6-TRIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE;2-PHENYL-4,4,6-TRIMETHYL-1,3,2-DIOXABORINATE;BENZENEBORONIC ACID-1,1,3-TRIMETHYLTRIMETHYLENE ESTER;2-Phenyl-4,4,6-trimethyl-1,3,2-dioxaborinane;Benzeneboronic acid, hexylene glycol ester
• CAS NO: 15961-35-0
• Molecular Formula: C₁₂H₁₇BO₂
• Molecular Weight: 204.07
• Mol File: 15961-35-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,4,6-TRIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,6-TRIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE(15961-35-0)
• EPA Substance Registry System: 4,4,6-TRIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE(15961-35-0)

Safety Data

• Hazardous Substances Data: 15961-35-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4,4,6-Trimethyl-2-phenyl-1,3,2-dioxaborinane is used as a reagent for the introduction of boron functional groups in the synthesis of various pharmaceuticals. Its ability to form stable complexes with transition metals aids in the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Production:
In the agrochemical industry, 4,4,6-Trimethyl-2-phenyl-1,3,2-dioxaborinane serves as a building block for the creation of novel agrochemicals. Its role in the synthesis of boron-containing compounds contributes to the development of more effective and targeted pest control agents.
Used in Material Science:
4,4,6-Trimethyl-2-phenyl-1,3,2-dioxaborinane is utilized as a key component in the synthesis of advanced materials, such as polymers and composites. Its incorporation into these materials enhances their properties, leading to improved performance in various applications.
Used in Organometallic Catalysis:
As a ligand in organometallic catalysis reactions, 4,4,6-Trimethyl-2-phenyl-1,3,2-dioxaborinane is employed to form stable complexes with transition metals. This enhances the efficiency and selectivity of catalytic processes, facilitating the synthesis of complex organic compounds with high yields and purity.

Upstream product

• 107-41-5 2-methyl-2,4-pentanediol 
• 2848-16-0 diphenyldiboronic acid 
• 591-50-4 iodobenzene 
• 10199-14-1 4,4,6-trimethyl-1,3,2-dioxaborinane 
• 108-86-1 bromobenzene 
• 61676-61-7 2-isopropoxy-4,4,6-trimethyl-[1,3,2] dioxaborinane 
• 100-58-3 phenylmagnesium bromide 
• 230299-21-5 4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron 
• 1538-62-1 triphenylantimony(V) diacetate 
• 98-80-6 phenylboronic acid 
• 109674-45-5 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide 
• 28249-75-4 2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 14190-17-1 diphenyliodonium acetate 
• 1483-72-3 diphenyliodonium chloride 

Downstream Products

• 26939-18-4 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine 
• 92-91-1 biphenyl-4-acetaldehyde 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 6301-56-0 ethyl 4-phenylbenzoate 
• 1008-88-4 3-phenylpyridine 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 28567-35-3 (tert-butoxymethylene)dibenzene 
• 92-52-4 biphenyl 
• 101-81-5 Diphenylmethane 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 713-36-0 2-benzyltoluene 
• 29921-41-3 (o-benzyl)chlorobenzene 
• 6639-40-3 1,2-bis(2-chlorophenyl)ethane 

Relevant articles and documents

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.

Photoinduced Miyaura Borylation by a Rare-Earth-Metal Photoreductant: The Hexachlorocerate(III) Anion

The first photoinduced carbon(sp2)–heteroatom bond forming reaction by a rare-earth-metal photoreductant, a Miyaura borylation, has been achieved. This simple, scalable, and novel borylation method that makes use of the hexachlorocerate(III) anion ([CeIIICl6]3?, derived from CeCl3) has a broad substrate scope and functional-group tolerance and can be conducted at room temperature. Combined with Suzuki–Miyaura cross-coupling, the method is applicable to the synthesis of various biaryl products, including through the use of aryl chloride substrates.

Nickel-catalysed decarbonylative borylation of aroyl fluorides

The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.

Tris(trimethylsilyl)silylboronate Esters: Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions

New, bulky tris(trimethylsilyl)silylboronate pinacol and hexylene glycol esters ((TMS)3Si-B(pin) and (TMS)3Si-B(hg)) were prepared in 46 and 61% yields, respectively, by the reaction of tris(trimethylsilyl)silylpotassium with the corresponding boron electrophiles. Notably, these silylboronate esters exhibited high stability to air and silica gel and were applied to the transition-metal-free boryl substitution of aryl halides, providing the desired borylated products in high yields with excellent B:Si ratios (up to 96% yield, B/Si = 99/1). These new silylboronate esters were also applied to a sequential borylation/cross-coupling process with various aryl halides, as well as the base-mediated silaboration of styrene.

Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes

A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C-H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C-H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. The potential utility of these methods in medicinal chemistry applications is highlighted.

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

A mild carbon-boron bond formation from diaryliodonium salts

The direct metal-free borylation of diaryliodonium salts with diboron reagents is now demonstrated to be a feasible process toward formation of aryl boronic esters without any additive or catalysts, and it can be extended to a two-step C-C coupling of both aryl groups of the initial diaryliodonium reagent.

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

Iron catalysis and water: A synergy for refunctionalization of boron

A new catalytic system has been optimized to promote the conversion of boron species into others. FeCl3 associated with imidazole and water favors boron refunctionalization under mild conditions. Georg Thieme Verlag Stuttgart New York.