5-BROMO-2-ETHOXY-4-PYRIDINEBORONIC ACID Chemical Properties

Melting point:

103-105 °C

Boiling point:

374.8±52.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

6.88±0.58(Predicted)

InChI

1S/C7H9BBrNO3/c1-2-13-7-3-5(8(11)12)6(9)4-10-7/h3-4,11-12H,2H2,1H3

InChIKey

RLPXRCAGOQMYBN-UHFFFAOYSA-N

SMILES

CCOc1cc(B(O)O)c(Br)cn1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

WGK 3

HS Code 

2933399990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

5-BROMO-2-ETHOXY-4-PYRIDINEBORONIC ACID Usage And Synthesis

Application

5-Bromo-2-ethoxypyridine-4-boronic acid is an organic intermediate that can be used in coupling reactions such as Suzuki, and is mainly used in laboratory research and development processes and chemical and pharmaceutical synthesis processes.

Synthesis

LDA (2.0 M in heptane-THF-ethylbenzene, 2.0 mL, 4.0 mmol) was added dropwise to a solution of 5-bromo-2-methoxypyridine (9) (727 mg, 3.9 mmol) in anhydrous THF (10 mL) at -78 ??C. The reaction mixture was stirred at -78 ??C for 1 h, then TIPB (1.5 g, 7.8 mmol) was added dropwise. The mixture was stirred at -78 ??C for 1 h, then quenched with H2O (10 mL) and allowed to warm to 20 ??C overnight. Post-treatment of the reaction solution (the aqueous layer was then acidified to pH 4 with 48% aqueous HBr to precipitate) gave the product 3-bromo-6-methoxy-4-pyridinylboronic acid. 5-Bromo-2-ethoxyarsenyl-4-boronic acid was synthesized with reference to the method described above from the following materials: a solution of 5-bromo-2-ethoxypyridine (10) (261 mg, 1.3 mmol), THF (10 mL), and LDA (2.0 M heptane-THF-ethylbenzene, 0.8 mL, 1.5 mmol). The product was a white solid (74 mg, 23%).

5-BROMO-2-ETHOXY-4-PYRIDINEBORONIC ACID(612845-46-2)Related Product Information

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