608534-44-7

Usage

Uses

Used in Organic Synthesis:
2-Indanylboronic Acid Pinacol Ester is used as a reagent in organic synthesis for the formation of stable cyclic boronate compounds. Its application is particularly valuable in reactions involving 1,2and 1,3-diols, where it forms 1,3,2-dioxaborolanes and 1,3,2-dioxaborinanes that can be isolated and further utilized in various chemical processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Indanylboronic Acid Pinacol Ester is used as an intermediate in the synthesis of complex organic molecules, including potential drug candidates. Its ability to form stable boronate compounds with specific diols makes it a useful building block for the development of new medicinal agents.
Used in Material Science:
2-Indanylboronic Acid Pinacol Ester is also utilized in material science for the development of new materials with unique properties. The stable cyclic boronate structures it forms can be incorporated into polymers, coatings, and other materials to enhance their characteristics, such as stability, reactivity, or selectivity.
Overall, 2-Indanylboronic Acid Pinacol Ester is a versatile chemical compound with applications in organic synthesis, pharmaceuticals, and material science, owing to its ability to form stable cyclic boronate compounds with specific diols.

InChI:InChI=1/C15H21BO2/c1-14(2)15(3,4)18-16(17-14)13-9-11-7-5-6-8-12(11)10-13/h5-8,13H,9-10H2,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 95-13-6 1-indene 
• 73183-34-3 bis(pinacol)diborane 
• 25177-85-9 2-indancarboxylic acid 
• 2975-41-9 2,3-dihydro-1H-inden-2-amine 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 54672-55-8 2,3-dihydro-1H-indene-2-carbonyl chloride 
• 17623-96-0 2-bromoindane 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1257661-35-0 4’,4’,5’,5’-tetramethyl-2’-(1-phenylbutan-3-yl)-1’,3’,2’-dioxaborolane 
• 67-56-1 methanol 

Downstream Products

• 1557201-10-1 potassium (2,3-dihydro-1H-inden-2-yl)trifluoroborate 

Relevant academic research and scientific papers

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Light-Mediated Sulfur-Boron Exchange

Interaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters is described. The reaction is promoted by an organic photocatalyst (3DPA2FBN) u

Method for directly preparing alkyl borate compound from alkyl halide

The invention relates to a method for directly preparing an alkyl borate compound from an alkyl halide, which comprises the following steps: in a protective atmosphere, mixing a titanium metal catalyst, an alkali compound, a borate compound and an alkyl halide or sulfonate compound, reacting at 35-100 DEG C for 8-24 hours, so that the alkyl halide or sulfonate compound is directly converted into the alkyl boronic acid pinacol ester compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate application range.

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.

Selective electrocatalytic hydroboration of aryl alkenes

Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco

Decarboxylative Borylation of Stabilized and Activated Carbon Radicals

Redox-active esters (RAEs) as active radical precursors have been extensively studied for C?B bond formations. However, the analogous transformations of stabilized radicals from the corresponding acid precursors remain challenging owing to the strong preference towards single-electron oxidation to the stable carbocations. This work describes a general strategy for rapid access to various aliphatic and aromatic boronic esters by mild photoinduced decarboxylative borylation. Both aryl and alkyl radicals could be generated from the leaving group-assisted N-hydroxybenzimidoyl chloride esters, even α-CF3 substituted substrates could be activated for further elaboration.

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.

Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones.

Metal catalyst-free photo-induced alkyl C-O bond borylation

Metal catalyst free, blue visible light-induced C-O bond borylation of unactivated tertiary alkyl methyl oxalates has been developed to furnish tertiary alkyl boronates. From the secondary alcohols activated with imidazolylthionyl, moderate yields of boronates were attained under standard photo-induced conditions. Preliminary mechanistic studies confirmed the involvement of a (DMF)2-B2cat2 adduct that weakly absorbs light at 437 nm so as to initiate a Bcat radical. A radical-chain process is proposed wherein the alkyl radical is engaged. This journal is

Divergent, Stereospecific Mono- and Difluoromethylation of Boronic Esters

There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH2F and CHF2 groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α-fluoro-boronic esters. These unique intermediates can be readily transformed into the corresponding mono- or difluoromethylated compounds through proto- or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2-migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.