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Product Name:    5-Bromo-2-chloropyrimidine

Synonyms:PYRIMIDINE, 5-BROMO-2-CHLORO-;
2-chloro-5-broMopyriMidine(5-broMo-2-chloropyriMidine);
2-chloro -5-broMo - uracil;
5 - broMine - 2 - chloro pyriMidine;
5-methyl-4,5-dihydrothiazol-2-amine;Macitentan Intermediate 5;
Macitentan Impurity 27;
5-BROMO-2-CHLOROPYRIMIDINE
CAS:    32779-36-5
MF:    C4H2BrClN2
MW:    193.43
EINECS:    629-214-8
Product Categories:    Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Pyrimidine Series;Halides;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Heterocycles;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Variety of halogenated heterocyclic series;Halogenated;Organohalides;Building Blocks;C4 to C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series;Pharmaceutical intermediates;Thiophenes;bc0001
Mol File:    32779-36-5.mol
5-Bromo-2-chloropyrimidine Structure
5-Bromo-2-chloropyrimidine Chemical Properties
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
pka    -2.84±0.22(Predicted)
form     Crystalline Powder
color     Off-white to beige
Water Solubility     insoluble
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 Information
Hazard Codes     Xi
Risk Statements     36/37/38
Safety Statements     26-36/39-37/39-36
RIDADR     UN 3335
WGK Germany     3
HazardClass     IRRITANT
HS Code     29335990

Uses    5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors.
Uses    5-Bromo-2-chloropyrimidine is applied as a pharmaceutical intermediate, in the synthesis of pharmaceutical goods such as inhibitors. It is also employed in the cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines.

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].