2-AMINO-5-BROMO-3-IODOPYRIDINE Chemical Properties

Melting point:

111-112°C

Boiling point:

308.2±42.0 °C(Predicted)

Density 

2.426±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.25±0.49(Predicted)

color 

White to Yellow to Orange

Sensitive 

Light Sensitive

InChI

InChI=1S/C5H4BrIN2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9)

InChIKey

XPERZSKJGNUSHI-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1I

CAS DataBase Reference

381233-96-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36:37/38-41-37/38-22

Safety Statements 

26-36/37/39-37

WGK Germany 

3

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29333990

MSDS

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2-AMINO-5-BROMO-3-IODOPYRIDINE Usage And Synthesis

Chemical Properties

Brown powder

Uses

2-Amino-5-Bromo-3-Iodopyridine is used as an important intermediate of pharmaceuticals and farm chemicals.

Synthesis

The general steps for the synthesis of 2-amino-3-iodo-5-bromopyridine from 2-amino-5-bromopyridine are as follows: Step 1: Iodination reaction 5-Bromo-pyridin-2-ylamine (50 g, 289 mmol) was dissolved in 2 M sulfuric acid (500 mL) and potassium iodate (30.8 g, 144 mmol) was added in batches. The mixture was heated to 100°C and an aqueous solution of potassium iodide (26.5 g, 160 mmol) was added slowly and dropwise (50 mL) over about 1 hour. After 1 hour of reaction, stirring was continued for 30 minutes, followed by cooling to room temperature. The pH of the aqueous phase was adjusted to 8-9 with alkali and then the mixture was extracted with ethyl acetate (3 times). The organic layers were combined and washed sequentially with aqueous sodium thiosulfate, water and brine, dried (Na2SO4) and concentrated to give 2-amino-3-iodo-5-bromopyridine as a brown solid (77.4 g, 90% yield). NMR data (300 MHz, CDCl3): δ 8.06 (d, J = 2.2 Hz, 1H), 7.96 (d, J = 2.2 Hz, 1H), 4.96 (s, 2H).

References

[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 10093 - 10096
[2] Angew. Chem., 2013, vol. 52, # 38, p. 10093 - 10096,4
[3] Patent: WO2011/73263, 2011, A1. Location in patent: Page/Page column 78
[4] Patent: WO2012/10538, 2012, A2. Location in patent: Page/Page column 28
[5] Patent: US2012/22258, 2012, A1. Location in patent: Page/Page column 13-14

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