| Identification | More | [Name]
4-Amino-2,6-dichloropyridine | [CAS]
2587-02-2 | [Synonyms]
2,6-DICHLORO-4-AMINOPYRIDINE
2,6-DICHLOROPYRIDIN-4-AMINE
2,6-DICHLORO-PYRIDIN-4-YLAMINE
4-AMINO-2,6-DICHLOROPYRIDINE
AURORA KA-3022
4-Pyridinamine, 2,6-dichloro-
2,6-dichloro-4-pyridinamine
2,6-Dichloropyridine-4-amine
4-Amino-2,6-dichloropyridine, 98+% | [EINECS(EC#)]
629-221-6 | [Molecular Formula]
C5H4Cl2N2 | [MDL Number]
MFCD00052832 | [Molecular Weight]
163 | [MOL File]
2587-02-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
169-173 °C (lit.) | [Boiling point ]
336.7±37.0 °C(Predicted) | [density ]
1.497±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
0.49±0.50(Predicted) | [color ]
White to buff | [BRN ]
114351 | [InChI]
InChI=1S/C5H4Cl2N2/c6-4-1-3(8)2-5(7)9-4/h1-2H,(H2,8,9) | [InChIKey]
WAEZOSSWRXDWAX-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC(Cl)=CC(N)=C1 | [CAS DataBase Reference]
2587-02-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Pyridine, 4-amino-2,6-dichloro-(2587-02-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
4-Amino-2,6-dichloropyridine is a compound useful in organic synthesis used in the synthesis of Rho kinase inhibitors. | [Synthesis]
The general procedure for the synthesis of 4-amino-2,6-dichloropyridine from 2,6-dichloro-4-nitropyridine was as follows: to a solution of 2,6-dichloro-4-nitropyridine (14.82 g, 76.79 mmol) in ethanol (350 mL) was added sequentially iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol), and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). The reaction was carried out at 95 °C with stirring for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the pH was adjusted to neutral. After filtration, the filtrate was concentrated and extracted with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to afford 11.9 g of the title product 4-amino-2,6-dichloropyridine in 95.1% yield. | [References]
[1] Patent: US2012/289497, 2012, A1. Location in patent: Page/Page column 51-52
[2] Patent: EP2524917, 2012, A1. Location in patent: Page/Page column 58-59
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[4] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 12, p. 2133 - 2144
[5] ChemCatChem, 2016, vol. 8, # 8, p. 1485 - 1489 |
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