845885-86-1

Basic information

• Product Name: 2-(4-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE
• Synonyms: 2-(4-PYRIDYL)-5,5-DIMETHYL-1,2,3-DIOXABORINANE;2-(3-PYRIDYL)-5,5-DIMETHYL-1,2,3-DIOXABORANE;2-(3-PYRIDYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE;2-(3-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE;PYRIDINE-3-BORONIC ACID, NEOPENTYL ESTER;PYRIDINE-3-BORONIC ACID NEOPENTYLGLYCOL ESTER;5,5-Dimethyl-2-(pyridin-3-yl)-1,3,2-dioxaborinane;3-PYRIDINEBORONIC ACID NEOPENTYLGLYCOL ESTER, 97%
• CAS NO: 845885-86-1
• Molecular Formula: C10H14BNO2
• Molecular Weight: 191.03
• Mol File: 845885-86-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 92-96 °C(lit.)
• Boiling Point: 309.8 °C at 760 mmHg
• Flash Point: 141.2 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0.00114mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.22±0.12(Predicted)
• CAS DataBase Reference: 2-(4-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE(845885-86-1)
• EPA Substance Registry System: 2-(4-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE(845885-86-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 845885-86-1(Hazardous Substances Data)

Usage

Uses

3-Pyridineboronic acid neopentylglycol ester can be used as a reactant: To synthesize N-alkyl-3-boronopyridinium salts by reacting with corresponding alkyl halides. In the ruthenium-catalyzed diastereoselective C-H bond α-arylation of cyclic amines. To prepare 2-(3-pyridyl)benzoxazole by reacting with benzoxazole via copper-catalyzed oxidative arylation reaction. In the Suzuki-Miyaura cross-coupling reaction.

InChI:InChI=1/C10H14BNO2/c1-10(2)7-13-11(14-8-10)9-3-5-12-6-4-9/h3-6H,7-8H2,1-2H3

Upstream product

• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1120-90-7 3-iodopyridine 

Downstream Products

• 7500-05-2 3-hydroxy-1-methylpyridin-1-ium iodide 
• 1624848-51-6 3-{5-[1-(pyrrolidin-1-yl)cyclohexyl]-1,3-thiazol-2-yl}pyridine 
• 109-00-2 3-HYDROXYPYRIDINE 

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.