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| | 2-Amino-4-chloropyrimidine Basic information |
| | 2-Amino-4-chloropyrimidine Chemical Properties |
| Melting point | 155-160 °C (dec.) | | Boiling point | 314.6±34.0 °C(Predicted) | | density | 1.437±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Soluble in dimethyl sulfoxide. | | pka | 3.55±0.10(Predicted) | | form | Solid | | color | White | | InChI | InChI=1S/C4H4ClN3/c5-3-1-2-7-4(6)8-3/h1-2H,(H2,6,7,8) | | InChIKey | DBGFGNCFYUNXLD-UHFFFAOYSA-N | | SMILES | C1(N)=NC=CC(Cl)=N1 | | CAS DataBase Reference | 3993-78-0(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-41-37/38-22 | | Safety Statements | 26-36/37/39-36/39-60 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 2-Amino-4-chloropyrimidine Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | 2-Amino-4-chloropyrimidine is a substrate used in a palladium-catalyzed cyanation with zinc(II) cyanide. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields. | | Synthesis | 2,4-Dichloropyrimidine (1.0 g, 6.7 mmol) was used as starting material and 28% w/v aqueous ammonium hydroxide solution (20 mL) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The obtained residue was dried and subsequently purified by fast column chromatography (FCC) with the eluent being chloroform solution containing 2-10% ethanol, resulting in the isolation of 2-amino-4-chloropyrimidine and 2-chloro-4-aminopyrimidine. Product yields: 200 mg of 2-amino-4-chloropyrimidine in 23% yield and 600 mg of 2-chloro-4-aminopyrimidine in 69% yield. | | Purification Methods | It has also been purified by sublimation in a vacuum and recrystrallisation from H2O. [Hilbert & Johnson J Am Chem Soc 52 1155 1930, Beilstein 24 H 80, 25 III/IV 2117.] | | References | [1] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 62
[2] Journal of the American Chemical Society, 2003, vol. 125, # 33, p. 9970 - 9982
[3] Tetrahedron, 2010, vol. 66, # 6, p. 1280 - 1288
[4] Patent: WO2006/114409, 2006, A1. Location in patent: Page/Page column 18
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 1973 - 1978 |
| | 2-Amino-4-chloropyrimidine Preparation Products And Raw materials |
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