4-AMINO-3,5-DIBROMOPYRIDINE Chemical Properties

Melting point:

165-170 °C

Boiling point:

292.9±35.0 °C(Predicted)

Density 

2.147

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.96±0.24(Predicted)

color 

Light yellow to Yellow to Orange

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-37/38-41

Safety Statements 

26-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333990

4-AMINO-3,5-DIBROMOPYRIDINE Usage And Synthesis

Chemical Properties

white solid

Uses

4-Amino-3,5-dibromopyridine is an important synthetic intermediate of a natural product Desmopyradine, can be converted into another important pyridine intermediate such as 3, 5-dibromopyridine, 3, 5-dibromo-4-iodopyridine and the like, and has important synthetic value.

Preparation

A preparation method of 4-Amino-3,5-dibromopyridine is characterized by comprising the following steps: pyridine or pyridine salt is taken as raw material, ammonium salt and H are added into HBr solution2O2And reacting in one step to obtain the 4-Amino-3,5-dibromopyridine.

Synthesis

General procedure for the synthesis of 4-amino-3,5-dibromopyridine from 4-aminopyridine: To a suspension of 4-aminopyridine (188.2 mg, 2.0 mmol, 1.0 eq.) in dichloromethane (10 mL) was added slowly over a period of 1 hour a dichloromethane (30 mL) solution of N-bromosuccinimide (818.7 mg, 4.6 mmol, 2.3 eq.). ) solution. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a mixture of succinimide and 4-amino-3,5-dibromopyridine. The mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1) to afford the target product 4-amino-3,5-dibromopyridine (464.8 mg, 1.84 mmol, 92% yield) as a colorless solid. Thin layer chromatography (TLC) Rf value was 0.62 (unfolding agent: hexane/ethyl acetate = 1/1). The melting point is 163-167 °C. Infrared spectrum (KBr, cm^-1): 3535, 3429, 3266, 3100, 2667, 2536, 2329, 1872, 1825, 1785, 1626, 1566, 1522, 1485, 1408, 1323, 1262, 1154, 1138, 1081, 1051, 892, 855. 747, 726, 658, 589, 573, 517, 468, 431.NMR hydrogen spectrum (300 MHz, CDCl3) δ 8.31 (2H, s, H2/6), 5.06 (2H, s, NH). NMR carbon spectra (75 MHz, CDCl3) δ 149.9, 147.8, 106.2. electron bombardment mass spectra (EI-MS) m/z calculated value C5H4Br2N2 [M]+ 249.87, measured value 249.90.

References

[1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Chemistry - A European Journal, 2012, vol. 18, # 20, p. 6328 - 6334
[3] Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1557 - 1563
[4] Patent: CN106957259, 2017, A. Location in patent: Paragraph 0015; 0017; 0019
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4575 - 4578

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