| Identification | More | [Name]
4,6-Dichloro-5-methoxypyrimidine | [CAS]
5018-38-2 | [Synonyms]
4,6-DICHLORO-5-METHOXYPYRIMIDINE
2,4-dimethoxy-2-methylmercapyrimidine
4,6-Dichlor-5-methoxypyrimidin
4,6-DICHLORO-5-METHOXYPYRIMIDINE 99%
2,4-Dichloro-5-methoxypyrimidine
Pyrimidine, 4,6-dichloro-5-methoxy- | [EINECS(EC#)]
225-699-1 | [Molecular Formula]
C5H4Cl2N2O | [MDL Number]
MFCD00087680 | [Molecular Weight]
179 | [MOL File]
5018-38-2.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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