| Identification | More | [Name]
2-Amino-4-chloropyrimidine | [CAS]
3993-78-0 | [Synonyms]
2-AMINO-4-CHLOROPYRIMIDINE
2-PYRIMIDINAMINE, 4-CHLORO-
4-CHLOROPYRIMIDIN-2-AMINE
AKOS BBS-00005838
CHLORO-ISO-CYTOSINE
2-Pyrimidinamine, 4-chloro-(9CI)
2-AMINO-4-CHLOROPYRIMIDINE, 98+%
2-amine-4-chloropyrimidine
4-Chloro-pyrimidin-2-ylamine
4-Chloro-2-pyrimidinamine
NSC 10872
NSC 25184
2-amino-4-chloridepyrimidine
2-amino-4-chloropyrimidein
2-Amino-4-chlor-pyrimidin
4-Chloropyrimidine-2-amine | [Molecular Formula]
C4H4ClN3 | [MDL Number]
MFCD00038021 | [Molecular Weight]
129.55 | [MOL File]
3993-78-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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. | [form ]
Solid | [pka]
3.55±0.10(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36/39:Wear suitable protective clothing and eye/face protection . | [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 |
| Hazard Information | Back Directory | [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 |
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