5-Bromo-2,4-dichloropyrimidine Chemical Properties

Melting point:

29-30 °C (lit.)

Boiling point:

128 °C/15 mmHg (lit.)

Density 

1.781 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.603(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ether (Slightly), Ethyl Acetate (Slightly), Toluene (Slightly)

form 

Liquid or Low Melting Solid

pka

-4.26±0.29(Predicted)

Specific Gravity

1.781

color 

Clear colorless to light yellow

BRN 

124441

InChI

InChI=1S/C4HBrCl2N2/c5-2-1-8-4(7)9-3(2)6/h1H

InChIKey

SIKXIUWKPGWBBF-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Br)C(Cl)=N1

CAS DataBase Reference

36082-50-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,C

Risk Statements 

23/24/25-34-43

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3263 8/PG 2

WGK Germany 

3

Hazard Note 

Toxic/Corrosive

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:5-Bromo-2,4-dichloropyrimidine
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5-Bromo-2,4-dichloropyrimidine Usage And Synthesis

Chemical Properties

Colourless Oil

Uses

Starting material for the synthesis of trisubstituted pyrimidines via a combination of nucleophilic substitution and palladium-catalyzed aryl cross-coupling.1

Uses

5-Bromo-2,4-dichloropyrimidine may be employed as starting reagent for the synthesis of positive allosteric modulators for GABA_B receptors (drug-like class of compounds) and pyridinepyrimidine analogs.

General Description

5-Bromo-2,4-dichloropyrimidine is a halogenoprimidine. It has been reported as an intermediate during the synthesis of 2,4-di-t-butoxy-5-bromopyrimidine and 2,4-di-t-butoxy-5-pyrimidineboronic acid.

Synthesis

General procedure for the synthesis of 5-bromo-2,4-dichloropyrimidine from 5-bromouracil: 5-bromouracil (6.0 g, 31.4 mmol) was placed in a reaction flask with phosphorus pentachloride (PCl5, 16.4 g, 87.9 mmol) and 1,1,2-trichloroethane (50 mL) was added as solvent. The reaction mixture was heated to reflux and the transformation of the mixture from suspension to a light yellow transparent solution was observed. The reaction progress was monitored by thin layer chromatography (TLC) and after confirming the complete conversion of the feedstock, the reaction mixture was cooled to room temperature. Subsequently, the reaction mixture was rapidly poured into stirred ice water and stirring was continued for 1 hour. The aqueous phase was extracted with dichloromethane (DCM, 3 x 50 mL), the organic layers were combined and dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed by evaporation under reduced pressure to give a light yellow transparent liquid crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the target compound 5-bromo-2,4-dichloropyrimidine as a colorless transparent liquid (99.5% yield, 97% purity).

References

[1] Patent: CN108117523, 2018, A. Location in patent: Paragraph 0039; 0041; 0043; 0044; 0045
[2] Purinergic Signalling, 2017, vol. 13, # 1, p. 89 - 103
[3] Patent: CN105237483, 2016, A. Location in patent: Paragraph 0039; 0040; 0041; 0042; 0043
[4] Patent: US4299961, 1981, A
[5] Journal of the American Chemical Society, 1934, vol. 56, p. 134,138

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