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| | 4,6-Dichloro-5-pyrimidinecarbaldehyde Basic information |
| Product Name: | 4,6-Dichloro-5-pyrimidinecarbaldehyde | | Synonyms: | 4,6-Dichloro-5-formylpyrimidine;4,6-DICHLOROPYRIMIDINE-5-CARBALDEHYDE,PURITY:97% MIN(HPLC);6-DichloropyriMidine-5-carboxaldehyde;5-PyriMidinecarbaldehyde, 4,6-dichloro-;4,6-Dichloro-5-pyrimidinecarbaldehyde ,96%;5-PyriMidinecarboxaldehyde, 4,6-dichloro-;4,6-Dichloro-5-formylpyrimidine, 4,6-Dichloro-5-formyl-1,3-diazine;4,6-Dichloropyrimidine-5-carboxaldehyde,97% | | CAS: | 5305-40-8 | | MF: | C5H2Cl2N2O | | MW: | 176.99 | | EINECS: | | | Product Categories: | Heterocycle-Pyrimidine series;Pyrimidine series;Carbonyl Compounds;Heterocycles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Pyrimidine | | Mol File: | 5305-40-8.mol |  |
| | 4,6-Dichloro-5-pyrimidinecarbaldehyde Chemical Properties |
| Melting point | 66-71 °C | | Boiling point | 92-93 °C(Press: 0.05 Torr) | | density | 1.588±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | form | solid | | pka | -5.90±0.26(Predicted) | | color | Yellow | | InChI | InChI=1S/C5H2Cl2N2O/c6-4-3(1-10)5(7)9-2-8-4/h1-2H | | InChIKey | XQSJHQXYQAUDFC-UHFFFAOYSA-N | | SMILES | C1=NC(Cl)=C(C=O)C(Cl)=N1 | | CAS DataBase Reference | 5305-40-8(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-43-36/38-22 | | Safety Statements | 26-36-36/37 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1 |
| | 4,6-Dichloro-5-pyrimidinecarbaldehyde Usage And Synthesis |
| Chemical Properties | White to off-white solid | | Uses | 4,6-Dichloropyrimidine-5-carboxaldehyde is used as a substrate in the synthesis of N-terminal surrogate in amino acid and peptide analogues. | | Synthesis | General procedure for the synthesis of 4,6-dichloro-5-pyrimidinecarboxaldehyde from N,N-dimethylformamide (DMF) and 4,6-dihydroxypyrimidine: First, DMF (64 mL) was mixed with phosphorus oxychloride (POCl3) (200 mL) and stirred for 1 hr at 0 °C. Subsequently, 4,6-dihydroxypyrimidine (50.0 g, 446 mmol) was added to the mixture and stirring was continued for 0.5 h at room temperature. Next, the resulting non-homogeneous mixture was heated to reflux for 3 hours. After completion of the reaction, the volatiles were removed by distillation under reduced pressure and the residue was carefully poured into ice water. The aqueous phase was extracted six times with ether and the organic phases were combined. The organic phase was washed sequentially with aqueous sodium bicarbonate (NaHCO3) and pure water and dried over anhydrous sodium sulfate (Na2SO4). The dried organic phase was concentrated under reduced pressure and finally crystallized by ethyl acetate (EtOAc)-petroleum ether mixed solvent to afford the target product 4,6-dichloro-5-pyrimidinecarboxaldehyde (43.5 g, 55% yield). The product was analyzed by LC-MS (ESI), m/z 177 [M+H]+. | | References | [1] Patent: US2006/281700, 2006, A1. Location in patent: Page/Page column 34
[2] Patent: US2006/281755, 2006, A1. Location in patent: Page/Page column 40
[3] Patent: US2006/281764, 2006, A1. Location in patent: Page/Page column 25
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3353 - 3358
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2936 - 2941 |
| | 4,6-Dichloro-5-pyrimidinecarbaldehyde Preparation Products And Raw materials |
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