5-Bromo-2-iodopyrimidine Chemical Properties

Melting point:

99-103 °C (lit.)

Boiling point:

341.0±34.0 °C(Predicted)

Density 

2.495±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-2.56±0.22(Predicted)

form 

Crystalline Powder

color 

White to tan

Sensitive 

Light Sensitive

InChI

InChI=1S/C4H2BrIN2/c5-3-1-7-4(6)8-2-3/h1-2H

InChIKey

ZEZKXPQIDURFKA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

183438-24-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-36/37/38

Safety Statements 

26-37/39-37

WGK Germany 

3

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromo-2-iodopyrimidine Usage And Synthesis

Chemical Properties

White solid

Uses

5-Bromo-2-iodopyrimidine can be used to synthesize 5,5′-dibromo-2,2′-bipyrimidine and O,O′-dimethyl hyrtinadine A.

General Description

5-Bromo-2-iodopyrimidine can be synthesized by reacting 5-bromo-2-chloropyrimidine with hydroiodic acid.

Synthesis

General procedure for the synthesis of 5-bromo-2-iodopyrimidine from 5-bromo-2-chloropyrimidine: 5-bromo-2-chloropyrimidine (5.80 g, 30 mmol) and sodium iodide (7.5 g, 50 mmol) were suspended in chloroform (20 mL), and hydriodic acid (57 wt%, 2.85 g, 25.6 mmol) was slowly added at 0 °C. After cooling was withdrawn, the reaction mixture was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was poured into a mixture of 200 mL of ice water with 30 mL of 10 N sodium hydroxide solution. Chloroform (150 mL) was added and stirred for 10 minutes. The organic phase was separated and the aqueous layer was extracted with chloroform (2 x 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 5-bromo-2-iodopyrimidine as a light yellow solid. Yield: 6.29 g (84%). Mass spectrum (MS): M = 284.8 (ESI+). 1H-NMR (300 MHz, CDCl3): δ 8.54 (s, 2H), 7.56 (d, J = 16.4 Hz, 1H), 7.59-7.66 (m, 4H).

References

[1] Angewandte Chemie - International Edition, 1999, vol. 38, # 5, p. 659 - 661
[2] Patent: US2005/222228, 2005, A1. Location in patent: Page/Page column 15-16
[3] Chemical Communications, 1996, # 24, p. 2719 - 2720
[4] Patent: US2012/238751, 2012, A1. Location in patent: Page/Page column 30
[5] Patent: WO2014/43272, 2014, A1. Location in patent: Paragraph 0411; 0412; 0413

5-Bromo-2-iodopyrimidine(183438-24-6)Related Product Information

• 4-Hydroxy-2,6-dimethylpyridine
• (R)-1-Boc-3-(hyroxymethyl)piperidine
• 2,3-Dibromopyridine
• 5-Bromo-1,2,3-trichlorobenzene
• 1,3-Dibromo-2,2-dimethoxypropane
• 7-Fluoro-6-nitro-4-hydroxyquinazoline
• (R)-3-Methylmorpholine hydrochloride
• 5-Bromopyrimidine
• Uracil
• Fluorocytosine
• Silver sulfadiazine
• Cytosine
• 4-Ethyl-5-fluoro-6-hydroxypyrimidine
• Sulfadiazine
• 5-Bromo-2-chloropyrimidine
• Bromine
• 2-Iodopyrimidine
• 5-Bromo-2-iodopyrimidine