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| | 5-Bromo-2,4-dichloropyrimidine Basic information |
| Product Name: | 5-Bromo-2,4-dichloropyrimidine | | Synonyms: | BUTTPARK 48\06-22;5-BROMO-2,4-DICHLOROPYRIMIDINE;TIMTEC-BB SBB003301;5-Bromo-2,4-Dichloropyridimidine;5-BROMO-2,4-DICHLOROPYRIMIDINE 99%;2,4-DICHLORO-5-BROMO PYRIMIDINE;5-Bromo-2,4-dichL;5-Bromo-2,4-dichloropyrimidine ,97% | | CAS: | 36082-50-5 | | MF: | C4HBrCl2N2 | | MW: | 227.87 | | EINECS: | 629-358-1 | | Product Categories: | Building Blocks;C4 to C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;pharmacetical;Halides;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Pyrimidine Series;Pyridines, Pyrimidines, Purines and Pteredines;Halogenated;Organohalides;Nucleotides and Nucleosides;Aromatics Compounds;Bases & Related Reagents;Nucleotides;Aromatics;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles | | Mol File: | 36082-50-5.mol |  |
| | 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.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), Ether (Slightly), Ethyl Acetate (Slightly), Toluene (Slightly) | | pka | -4.26±0.29(Predicted) | | form | Liquid or Low Melting Solid | | 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) |
| 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 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Eye Dam. 1
Skin Corr. 1B
Skin Sens. 1 |
| | 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 GABAB 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 |
| | 5-Bromo-2,4-dichloropyrimidine Preparation Products And Raw materials |
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