2-chloro-5-nitropyrimidine Chemical Properties

Boiling point:

279.6±28.0 °C(Predicted)

Density 

1.422±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Off-white to pink Solid

InChI

InChI=1S/C9H9BrO/c1-6-3-8(5-11)4-7(2)9(6)10/h3-5H,1-2H3

InChIKey

USONNBCBJMNJIU-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(C)=C(Br)C(C)=C1

2-chloro-5-nitropyrimidine Usage And Synthesis

Synthesis

Step 1: To a solution of 2,5-dibromo m-xylene (2.0 g, 7.6 mmol) in dichloromethane (20 ml) was slowly added n-butyllithium (n-BuLi, 2.5 M hexane solution, 3 ml, 1.0 eq.) at -78 °C. The reaction mixture was stirred at -78 °C for 1 h. After that, N,N-dimethylformamide (DMF, 1.8 ml, 23 mmol, 3 eq.) was added, followed by slow warming of the reaction system to room temperature. Upon completion of the reaction, the pH was adjusted to 2 with 5% aqueous hydrochloric acid and then extracted with ether (3 x 50 ml). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether (PE):ethyl acetate (EA) = 10:1 to afford 4-bromo-3,5-dimethylbenzaldehyde (0.76 g, 47% yield).

References

[1] European Journal of Organic Chemistry, 2001, # 20, p. 3819 - 3829
[2] Patent: EP2128158, 2009, A1. Location in patent: Page/Page column 21
[3] Patent: US2008/194670, 2008, A1. Location in patent: Page/Page column 49
[4] Patent: WO2006/100631, 2006, A1. Location in patent: Page/Page column 132
[5] Dyes and Pigments, 2018, vol. 155, p. 323 - 331

2-chloro-5-nitropyrimidine(400822-47-1)Related Product Information

• 4-BROMO-3,5-DIMETHYL-BENZAMIDE
• 4-BROMO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER
• 2-chloro-5-nitropyrimidine