| Identification | More | [Name]
5-Bromo-2-chloropyrimidine | [CAS]
32779-36-5 | [Synonyms]
2C5BP
2-CHLORO-5-BROMOPYRIMIDINE
5-BROMO-2-CHLOROPYRIMIDINE
5-BROMO-2-CHLOROPYRIMIDNE
PYRIMIDINE, 5-BROMO-2-CHLORO-
5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM85%)
MAJORIMPURITYIS2,5-DIBROMOPYRIMIDINE
5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM95%)
5-Bromo-2-chloropyrimidine 85%
5-Bromo-2-chloropyrimidine, 98+% | [EINECS(EC#)]
629-214-8 | [Molecular Formula]
C4H2BrClN2 | [MDL Number]
MFCD00483232 | [Molecular Weight]
193.43 | [MOL File]
32779-36-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to beige crystalline powder | [Melting point ]
73-79 °C (lit.) | [Boiling point ]
95°C 15mm | [density ]
1.859±0.06 g/cm3(Predicted) | [Fp ]
95°C/15mm | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
-2.84±0.22(Predicted) | [color ]
Off-white to beige | [Water Solubility ]
insoluble | [Detection Methods]
HPLC,NMR | [BRN ]
507955 | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C4H2BrClN2/c5-3-1-7-4(6)8-2-3/h1-2H | [InChIKey]
XPGIBDJXEVAVTO-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C(Br)C=N1 | [CAS DataBase Reference]
32779-36-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
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 .
S36/39:Wear suitable protective clothing and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3335 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29335900 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to beige crystalline powder | [Uses]
5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors. | [Preparation]
Under nitrogen protection, 35 g (0.2 mol) of 2-hydroxy-5-bromopyrimidine, 61.3 g (0.4 mol) of phosphorus oxychloride, and 200 mL of toluene were added into the reaction flask. At 35 ℃, triethylamine 40.5g was added and then heated up at 80-85 ℃. Stir the reaction for 6 hours, sampling HPLC to detect the raw material (less than 2%), and lower the temperature. After concentrating the mixture under reduced pressure to remove most of the toluene and Phosphorus oxychloride, put the reaction solution into 10°C water, and adjust pH=8-9 with 20% sodium carbonate aqueous solution. Finally, 5-Bromo-2-chloropyrimidine was obtained after purification. | [Reactivity Profile]
5-Bromo-2-chloropyrimidine, a 2,5-dihalopyrimidine, is a useful organic electrophiles. It could react with tri(3-indolyl)indium reagent through cross-coupling reaction. Other aryl- and heteroarylindium
reagents, such as thiophenyl-, pyridyl-, naphthyl-, and
alkynylindium reagents, also reacted with 5-bromo-2-
chloropyrimidine to afford the corresponding 2-chloro-5-substituted pyrimidines[1].
| [References]
[1] Mosquera A, et al. Cross-Coupling Reactions of Indium Organometallics with 2,5-Dihalopyrimidines: Synthesis of Hyrtinadine A?. Organic Letters, 2008; 10: 3745–3748.
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