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Pyridin-3-ylboronic acid

Pyridin-3-ylboronic acid structure

CAS No:
1692-25-7
Formula:
C5H6BNO2
Chemical Name:
Pyridin-3-ylboronic acid
Synonyms:
Boronic acid,B-3-pyridinyl-;3-Pyridineboronic acid;Boronic acid,3-pyridinyl-;B-3-Pyridinylboronic acid;3-Pyridylboronic acid;(3-Pyridinyl)boronic acid;Dihydroxy(3-pyridyl)borane;Pyridin-3-ylboronic acid;1401311-60-1;1628674-20-3
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Light Yellow Powder

Pyridin-3-ylboronic acid Basic Attributes

Molecular Weight：

122.92

Exact Mass：

122.92

BRN：

471943

DSSTox ID：

DTXSID30370268

HScode：

29349990

Characteristics

PSA：

53.4

XLogP3：

-1.23860

Appearance：

White to yellow-orange Powder, Crystals and/or Chunks

Density：

1.22±0.1 g/cm3(Predicted)

Melting Point：

>300 °C(lit.)

Boiling Point：

308.8±34.0 °C(Predicted)

Flash Point：

140.5±25.7 °C

Refractive Index：

1.534

Water Solubility：

Slightly soluble in methanol.

Storage Conditions：

0-6°C

Vapor Pressure：

0.000288mmHg at 25°C

Safety Information

Hazard category：

IRRITANT, KEEP COLD

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-22-34-11

safety instructions：

36/37/39-3-26-45-16

Marks：

Xn,Xi,C,F

Hazard note：

Irritant

Precautionary statement(s)：

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

GHS Classification：

|Warning|H302 (18.18%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 11 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

3-pyridineboronic acid

Pyridin-3-ylboronic acid Use and Manufacturing

Methods of Manufacturing

General Procedure for the Preparation of Pyridin-3-yl-Boronic Acids (1-6).; [0275] 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. [0276]/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.

Uses

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.

Computed Properties

Molecular Weight:122.92
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:123.0491586
Monoisotopic Mass:123.0491586
Topological Polar Surface Area:53.4
Heavy Atom Count:9
Complexity:89
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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