| Identification | More | [Name]
2-Chloro-4,6-dimethoxypyrimidine | [CAS]
13223-25-1 | [Synonyms]
2-CHLORO-4,6-DIMETHOXYPYRIMIDINE
PYRIMIDINE, 2-CHLORO-4,6-DIMETHOXY-
4-methoxybenzoicacidsodium
2-CHLOR-4,6-DIMETHOXYPYRIMIDINE
2-CHLORO-4,6-DIMETHOXYPYRIMIDINE 98+% | [EINECS(EC#)]
603-561-5 | [Molecular Formula]
C6H7ClN2O2 | [MDL Number]
MFCD00274530 | [Molecular Weight]
174.58 | [MOL File]
13223-25-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [Melting point ]
100-105 °C | [Boiling point ]
317.1±22.0 °C(Predicted) | [density ]
1.285±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
powder to crystal | [pka]
-1.46±0.30(Predicted) | [color ]
White to Light yellow | [Usage]
2-Chloro-4,6-dimethoxypyrimidine is used as building block in chemical synthesis. Product Data Sheet | [BRN ]
880035 | [InChIKey]
PBEKEFWBLFBSGQ-UHFFFAOYSA-N | [CAS DataBase Reference]
13223-25-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Chemical Properties]
White Powder | [Uses]
2-Chloro-4,6-dimethoxypyrimidine is a useful reactant for the synthesis of polycyclic fused and spiro-?4-?aminopyridines | [Uses]
2-Chloro-4,6-dimethoxypyrimidine is used as building block in chemical synthesis. Product Data Sheet | [Synthesis]
General procedure for the synthesis of 2-chloro-4,6-dimethoxypyrimidine from 2-amino-4,6-dimethoxypyrimidine:
1. 1,260 ml of 36% hydrochloric acid was added to a 5-liter four-necked flask and subsequently cooled to 0°C.
2. 180 g (1.16 moles) of 2-amino-4,6-dimethoxypyrimidine was added to the flask in batches and stirred continuously for about 1 hour until the reaction mixture took on a syrupy consistency.
3. After the reaction mixture was further cooled to -15°C, 260 ml of an aqueous solution containing 159 g (2.3 moles) of NaNO2 was slowly added dropwise over a period of about 1 hour under vigorous stirring.
4. after completion of the dropwise addition, the mixture was continued to be stirred at -15°C to -10°C for 1 hour to ensure complete reaction.
5. While keeping the reaction mixture at -5°C, 1.5 liters of 30% aqueous NaOH was slowly added dropwise to adjust the pH to 7 for neutralization.
6. The resulting purple clay-like substance was collected by filtration under reduced pressure.
7. the target compound 2-chloro-4,6-dimethoxypyrimidine was extracted from the clay-like material using 3 liters of ethyl acetate.
8. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was removed to yield 63 g of light blue crude crystals.
9. Purification and crystallization by silica gel chromatography resulted in 60.8 g of white crystals (yield: 29.9%) with a melting point of 101.5°-102.5°C. The final product was purified by silica gel chromatography. | [References]
[1] Patent: US4986846, 1991, A
[2] Pesticide Science, 1996, vol. 47, # 2, p. 103 - 114 |
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