2-Chloro-5-iodopyrimidine Chemical Properties

Melting point:

133.0 to 137.0 °C

Boiling point:

318℃

Density 

2.187

Flash point:

146℃

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

-2.78±0.22(Predicted)

color 

White to Gray to Brown

Sensitive 

Light Sensitive

InChI

InChI=1S/C4H2ClIN2/c5-4-7-1-3(6)2-8-4/h1-2H

InChIKey

WSZRCNZXKKTLQE-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(I)C=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933.59.8000

2-Chloro-5-iodopyrimidine Usage And Synthesis

Description

2-Chloro-5-iodopyrimidine is 2-Chloro-5-iodopyridine is a halo-substituted pyridine, and it is used in biology application as synthesis intermediate in the multi-step synthesis.

Synthesis

Step A. Preparation of 2-chloro-5-iodopyrimidine To a stirred solution of 5-iodopyrimidin-2-amine (2.21 g, 10.0 mmol) in acetonitrile (20 mL) was sequentially added copper(II) chloride (2.02 g, 15 mmol) and tert-butyl nitrite (1.55 g, 15 mmol) at room temperature and under argon protection. The reaction mixture was transferred to an oil bath preheated to 60 °C and reacted under argon atmosphere. After completion of the reaction, the mixture was cooled to room temperature and diluted with the addition of ether (20 mL). The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was dissolved in a small amount of dichloromethane (about 2 mL) and purified by passing through an 80 g ISCO silica gel column using a 20 min gradient elution (0% to 100% ethyl acetate/hexane). 2-Chloro-5-iodopyrimidine (778 mg, 31% yield) was finally obtained as an off-white solid.1H NMR (400 MHz, CDCl3) δ 8.79 (s, 2H).

References

[1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[2] Patent: WO2010/9183, 2010, A1. Location in patent: Page/Page column 79
[3] Patent: US4248618, 1981, A
[4] Patent: WO2013/186692, 2013, A1. Location in patent: Page/Page column 62

2-Chloro-5-iodopyrimidine(32779-38-7)Related Product Information

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• 4-Chloro-5-iodopyrimidine
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• 4-AMINO-2-CHLORO-5-IODOPYRIMIDINE
• 2-Chloro-5-iodopyrimidine
• 2, 4-DICHLORO-5-IODOPYRIMIDINE
• 2,4-dichloro-5-iodo-6-methylpyrimidine