| Identification | More | [Name]
6-Chloropyrimidin-4(3H)-one | [CAS]
4765-77-9 | [Synonyms]
4-CHLORO-6-HYDROXYPYRIMIDINE
6-CHLORO-4-HYDROXYPYRIMIDINE
6-Chloro-4-pyrimidinol
6-CHLOROPYRIMIDIN-4(3H)-ONE
6-CHLOROPYRIMIDIN-4-OL
4(1H)-Pyrimidinone, 6-chloro-(9CI)
6-Chloro-4(1H)-Pyrimidinone
6-CHLORO-4-HYDROXYPYRIMIDINE,98%
6-chloropyrimidin-4(1H)-one
4-Chloropyrimidin-6-one
6-chloro-4(3H)-Pyrimidinone
NSC 618279
4(1H)-Pyrimidinone, 6-chloro- | [EINECS(EC#)]
678-368-2 | [Molecular Formula]
C4H3ClN2O | [MDL Number]
MFCD06200891 | [Molecular Weight]
130.53 | [MOL File]
4765-77-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White to Pale Yellowish Solid | [Melting point ]
194 °C | [Boiling point ]
199.4±50.0 °C(Predicted) | [density ]
1.55±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO, Water | [form ]
Solid | [pka]
6.92±0.40(Predicted) | [color ]
Off-White to Pale Yellowish | [CAS DataBase Reference]
4765-77-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HS Code ]
2933599590 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to Pale Yellowish Solid | [Uses]
4-Chloro-6-hydroxypyrimidine (cas# 4765-77-9) is a compound useful in organic synthesis. | [Definition]
ChEBI: 6-Chloro-4-pyrimidinol is an organohalogen compound and a member of pyrimidines. | [Synthesis]
The general procedure for the synthesis of 6-chloropyrimidin-4(3H)-ones from 4,6-dichloropyrimidines is as follows:
Intermediate 1: Synthesis of 6-chloro-3H-pyrimidin-4-one
4,6-Dichloropyrimidine (Aldrich; 10.00 g, 67.1 mmol), concentrated hydrochloric acid (50 mL), water (50 mL), and dioxane (50 mL) were mixed and heated at 70 °C for 6 h, and subsequently cooled to room temperature to obtain a pink solution. The solvent was removed by evaporation under reduced pressure (using a vacuum pump) to obtain a pink solid. Ethanol (50 mL) was added to the solid and the mixture was heated until the solid was completely dissolved. The solution was cooled slowly in a warm water bath at about 50°C. After standing overnight, it was filtered to obtain an off-white solid, 6-chloro-3H-pyrimidin-4-one (5.02 g, 57% yield), with a melting point of 193-194°C (literature value: 192-193°C, see DJ Brown and JS Harper, J. Chem. Soc. 1961, 1298-1303).
1H NMR (d6-DMSO) data: δ 6.50 (s, 1H), 8.19 (s, 1H), 13.00 (br s, 1H). | [References]
[1] Journal of the Chinese Chemical Society, 2013, vol. 60, # 1, p. 27 - 34
[2] Patent: US2009/149466, 2009, A1
[3] Patent: WO2017/59080, 2017, A1. Location in patent: Page/Page column 288; 289 |
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