256652-04-7

Basic information

• Product Name: NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER
• Synonyms: NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER;2-NAPHTHALENEBORONIC ACID, PINACOL ESTER;2-Naphthaleneboronic acid, pinacol ester ,98%;2-(Naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-TetraMethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(2-naphthyl)-1,3,2-dioxaborolane
• CAS NO: 256652-04-7
• Molecular Formula: C₁₆H₁₉BO₂
• Molecular Weight: 254.13
• Mol File: 256652-04-7.mol

Chemical Properties

• Melting Point: 64.0 to 68.0 °C
• Boiling Point: 378.681 °C at 760 mmHg
• Flash Point: 182.82 °C
• Appearance: /Solid
• Density: 1.064 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER(256652-04-7)
• EPA Substance Registry System: NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER(256652-04-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 256652-04-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER is used as a key intermediate for the synthesis of various organic compounds due to its unique chemical properties and reactivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER is used as a building block for the development of new drugs, taking advantage of its chemical versatility and potential to form diverse molecular structures.
Used in Agrochemicals:
NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER is utilized as an intermediate in the production of agrochemicals, such as pesticides and fertilizers, where its chemical properties contribute to the effectiveness and stability of the final products.
Used in Dyestuffs:
In the dyestuffs industry, NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER is employed as a crucial intermediate for the synthesis of various dyes and pigments, leveraging its chemical structure to achieve a wide range of colors and properties.

InChI:InChI=1/C16H19BO2/c1-15(2)16(3,4)19-17(18-15)14-10-9-12-7-5-6-8-13(12)11-14/h5-11H,1-4H3

Upstream product

• 580-13-2 2-bromonaphthalene 
• 613-46-7 2-naphthalenecarbonitrile 
• 951887-43-7 2-(2-chloroallyl)naphthalene 
• 91-20-3 naphthalene 

Downstream Products

• 580-13-2 2-bromonaphthalene 
• 613-46-7 2-naphthalenecarbonitrile 
• 951887-43-7 2-(2-chloroallyl)naphthalene 
• 91-20-3 naphthalene 

Relevant articles and documents

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex

A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.

BORON DIIODIDE COMPOUND, AND BORONIC ACID, BORONIC ESTER AND THE LIKE OBTAINED THEREFROM, AND PRODUCTION METHOD OF THEM

PROBLEM TO BE SOLVED: To provide a method which enables simple production of a boronic acid, a boronic ester compound or the like suitable for production of various compounds. SOLUTION: The problem is solved by a boron diiodide compound represented by the following general formula (Y). (In the formula (Y), Ar is an n-valent heteroaryl ring, aryl ring having 10 or more carbon atoms, or substituted benzene ring, where at least one hydrogen atom in these rings may be substituted; n is an integer from 1 to 6; and at least one hydrogen atom in the compound represented by the formula (Y) may be substituted with deuterium.) COPYRIGHT: (C)2019,JPO&INPIT

Rhodium-catalyzed borylation of aryl and alkenyl pivalates through the cleavage of carbonoxygen bonds

Rhodium-catalyzed borylation reactions of aryl and alkenyl pivalates, using a diboron reagent, via the cleavage of carbonoxygen bonds have been developed. The inert nature of the pivalate moiety enables relatively complex aryl boronates to be synthesized via the tandem cross-coupling of carbonhalogen and carbonoxygen bonds.

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: Borylative removal of the directing group

The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.

Application of cooperative iron/copper catalysis to a palladium-free borylation of aryl bromides with pinacolborane

A new cooperative copper/iron catalysis for the borylation of various aryl bromides with pinacolborane, at -10 °C, is reported. Use of the toxic, precious metal Pd is avoided. The mechanism of the protodebromination side reaction is discussed.

Efficient borylation of reactive aryl halides with MPBH (4,4,6-trimethyl-1,3,2-dioxaborinane)

The combination of 4,4,6-trimethyl-1,3,2-dioxaborinane, a particularly stable and inexpensive borylation reagent, and Buchwalds palladium catalyst provides a simple, fast, cost-effective borylation of electron-rich, reactive iodides, bromides, and triflates to produce stable, easily purified boronic esters. Georg Thieme Verlag Stuttgart New York.

Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: Structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters

The selectivity of the iridium boryl complex-catalysed reaction of pyrene and perylene with B2(pin)2 (pin = OCMe2CMe 2O) has been employed in the synthesis of D2h-symmetry pyrene-2,7-(Bpn)2 and D4h-symmetry perylene-2,5,8,11- (Bpin)4 providing direct borylation of positions which are otherwise difficult to derivatise. The Royal Society of Chemistry 2005.