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
• Article Data: 9

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

Description

NAPHTHALENE-2-BORONIC ACID, PINACOL ESTER is a white solid that serves as an important raw material and intermediate in various chemical industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs.

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

• 91-20-3 naphthalene 
• 73183-34-3 bis(pinacol)diborane 
• 580-13-2 2-bromonaphthalene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 680192-98-7 deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 24550-07-0 2-(naphthalen-2-yloxy)pyridine 
• 1503-86-2 2-naphthyl pivalate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13517-10-7 boron triiodide 
• 91-58-7 2-chloronaphthalene 
• 67-56-1 methanol 

Downstream Products

• 612-78-2 2,2'-binaphthalene 
• 1501954-10-4 trimethyl((2-(naphthalen-2-yl)phenyl)ethynyl)silane 

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

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.

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.