4,6-Dichloro-5-methoxypyrimidine Chemical Properties

Melting point:

54-58 °C

Boiling point:

257.8±35.0 °C(Predicted)

Density 

1.446±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Dichloromethane (Slightly)

form 

Solid

pka

-4.13±0.26(Predicted)

color 

White

InChI

InChI=1S/C5H4Cl2N2O/c1-10-3-4(6)8-2-9-5(3)7/h2H,1H3

InChIKey

IJQIGKLDBGKSNT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5018-38-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933599590

4,6-Dichloro-5-methoxypyrimidine Usage And Synthesis

Chemical Properties

Off-white solid

Uses

4,6-Dichloro-5-methoxypyrimidine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

Example 3.2 Preparation of 4,6-dichloro-5-methoxypyrimidine: 5-methoxypyrimidine-4,6-diol (96.0 g, 676 mmol) and triethylamine (95.0 mL, 680 mmol) were suspended in anhydrous toluene (1.2 L) and heated to 100-105°C. A solution of anhydrous toluene (200 mL) with trichlorophosphate (140 mL, 1.5 mol) was added slowly and dropwise over 30 min. The reaction mixture was refluxed for 1 hour and cooled to room temperature. The toluene layer was decanted and ice water was added to the residue. The heavier black oil layer was separated, dilution was continued with ice water, and the mixture was extracted with toluene (2 x 200 mL). The toluene extracts were combined and the aqueous layer discarded. The organic phase was washed sequentially with saturated sodium bicarbonate solution (2×300 mL), saturated saline (400 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the title compound 4,6-dichloro-5-methoxypyrimidine (103.4 g, 86% yield) as a white solid.1H NMR (CDCl3) δ 4.00 (s, 3H), 8.55 (s, 1H).

References

[1] Patent: US2009/286816, 2009, A1. Location in patent: Page/Page column 12
[2] Patent: EP714896, 1996, A1
[3] Patent: US2006/52398, 2006, A1. Location in patent: Page/Page column 39
[4] Patent: US5300506, 1994, A
[5] Patent: US5077293, 1991, A

4,6-Dichloro-5-methoxypyrimidine(5018-38-2)Related Product Information

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