Chemical Products 3-Pyridylboronic acid Description
Light Yellow Powder
Chemical Products 3-Pyridylboronic acid Basic Attributes
Molecular Formula ：C5H6BNO2
Molecular Mass ：122.92
Exact Mass ：123.049156
PSA ：53.4 A^2
H-bond Acceptor ：3
H-bond Donor ：2
Chemical Products 3-Pyridylboronic acid Characteristics
Appearance ：White to yellow-orange Powder, Crystals and/or Chunks
Density ：1.22±0.1 g/cm3(Predicted)
Melting Point ：>300 °C(lit.)
Bolling Point ：308.8±34.0 °C(Predicted)
Flash Point ：140.5±25.7 °C
Refractive Index ：1.534
Solubility ：Slightly soluble in methanol.
Storage Condition ：0-6°C
Chemical Products 3-Pyridylboronic acid Safety Information
Hazard Class ：IRRITANT, KEEP COLD
HS Code ：29349990
UN No. ：NONH for all modes of transport
Risk Code ：36/37/38-22-34-11
Safety Instructions ：36/37/39-3-26-45-16
Dangerous Mark ：Xn,Xi,C,F
P Code ：P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Hazard Statements ：H302
Hazard Note ：Irritant
Chemical Products 3-Pyridylboronic acid Product Usage
Pyridine-3-boronic acid is a boric acid substance that can be used in the Suzuki reaction. It is mainly used in laboratory organic synthesis and in the development of chemical medicine.
Chemical Products 3-Pyridylboronic acid Production Methods
General Procedure for the Preparation of Pyridin-3-yl-Boronic Acids (1-6).;  Compounds 1-6 were prepared by the esterification of the appropriate lithiopyridine followed by hydrolysis as previously reported (Cai et al., Tetrahedron Lett. 43: 4285-4287 (2002) ). The synthesis of pyridin-3-yl-3-boronic acid (1) is representative of compounds 2-6. /Pyridin-3-yl-3-boronic acid (1). A 500 mL 3-neck flask was charged with toluene (85 mL), cooled to below-60 °C and a solution of n-BuLi (1.6 M in hexanes, 48.6 mL, 77.8 mmol) was added dropwise over 10 min. After the internal temperature reached-60 °C a solution of 3-bromopyridine (6.8 mL, 70.7 mmol) in toluene (30 mL) was added drop wise to keep the internal temperature below-50 °C. A brownish-black solid precipitated and the resultant slurry was stirred for 20 min. THF (30 mL) was added drop-wise to keep the internal temperature below-50 °C and the resultant slurry was stirred for 15 min. To the slurry was added triisopropyl borate (19.6 mL, 84.9 mmol) in one portion via syringe. The solution was warmed to-15 °C, quenched with HCl (aq) (2.7 N, 70.0 mL) and transferred to a separatory funnel. The aqueous layer was collected and the organic layer was washed with water (10 mL), the combined aqueous layers were neutralized to pH 7 with NaOH (aq) (10 N) and extracted with THF (200 mL x 1,125 mL x 2). The combined organics were concentrated in vacuo and the residue was dissolved in THF/CH30H (1: 1, 140 mL), filtered and diluted to 300 mL with CH3CN. The solvent was switched to CH3CN by distillation and concentrated to 100 mL. The solids were collected by filtration to afford the title compound 1 (6.4 g, 73percent yield) as an off white solid : 1H NMR (CD30D) 6 8.64 (br s, 1H), 8.50 (m, 1H), 8.38 (br s, 1H), 7.65 (br s, 1H). This material was used directly in Suzuki cross coupling reactions.
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