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)

Flash point:

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

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromo-2-chloropyrimidine Usage And Synthesis

Description

5-Bromo-2-chloropyrimidine is a halogenated pyrimidine analogue containing chloro and bromo substituents at positions 2 and 5 of the benzene ring structure. The compound is used as a pharmaceutical intermediate in the preparation of macitentan, an endothelin receptor antagonist drug for the treatment of pulmonary hypertension.

Chemical Properties

Off-white to beige crystalline powder

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.

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.

5-Bromo-2-chloropyrimidine(32779-36-5)Related Product Information

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