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Pyridine-4-boronic acid

Pyridine-4-boronic acid structure

CAS No:
1692-15-5
Formula:
C5H6BNO2
Chemical Name:
Pyridine-4-boronic acid
Categories:
Chemical Reagents > Organic Reagents

Description

light orange granular powderPyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.

Pyridine-4-boronic acid Basic Attributes

Molecular Weight：

122.918

Exact Mass：

123.049156

DSSTox ID：

DTXSID90370269

HScode：

29339900

Characteristics

PSA：

53.4

XLogP3：

0.10

Appearance：

light orange granular powder

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

Storage Conditions：

0-6ºC

Vapor Pressure：

6.52E-05mmHg at 25°C

Safety Information

Hazard category：

IRRITANT, KEEP COLD

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22;R36/37/38

safety instructions：

22-24/25-36/37/39-26-45-16

Marks：

Xn,Xi,C,F

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 (16.67%): 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 15 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4-pyridineboronic acid

Pyridine-4-boronic acid Use and Manufacturing

Methods of Manufacturing

In the Ar gas protection, 4-Bromo-pyridine (1.5 g; 10 mmol) was placed in a 200 ml Schlenk flask, After addition of 40 ml of anhydrous deoxygenated tetrahydrofuran, The reaction mixture was cooled to -78 ° C in a low temperature reactor, 5 ml (2.2 M; 11 mmol) of butyllithium was added dropwise, After reaction for 1 h, 4 ml of methyl borate was added, Low temperature reaction 1h and removed overnight.The reaction was quenched with 2 mol / L dilute hydrochloric acid, After recrystallization from n-hexane 0.8 g (0.8 g, 65percent yield) was obtained.

Uses

Pyridine-4-boronic acid can be used as a candidate for Suzuki-Miyaura coupling reaction. Especially, as a N-containing building blocks, pyridine-4-boronic acid was employed to construct some heterocyclic compounds with superior biological activities.
suzuki reaction Boronic acid derivatives and their binding affinities with diols.

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:83
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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