| Identification | More | [Name]
4-IODO-PYRIDIN-3-YLAMINE | [CAS]
105752-11-2 | [Synonyms]
3-AMINO-4-IODOPYRIDINE
4-IODO-PYRIDIN-3-YLAMINE
4-IODO-3-AMINOPYRIDINE
4-Iodopyridin-3-amine
3-amine-4-iodopyridin | [EINECS(EC#)]
678-659-4 | [Molecular Formula]
C5H5IN2 | [MDL Number]
MFCD04971334 | [Molecular Weight]
220.01 | [MOL File]
105752-11-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
69.2-69.5°C | [Boiling point ]
327.2±27.0 °C(Predicted) | [density ]
2.055 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
solid | [pka]
4.79±0.18(Predicted) | [Appearance]
Light yellow to brown Solid | [Sensitive ]
Air & Light Sensitive | [InChI]
InChI=1S/C5H5IN2/c6-4-1-2-8-3-5(4)7/h1-3H,7H2 | [InChIKey]
ZJRSKTXMSIVNAU-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(I)=C1N | [CAS DataBase Reference]
105752-11-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
22-37/38-41 | [Safety Statements ]
26-39 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
3-Amino-4-iodopyridine is a heterocyclic derivative and can be used as a pharmaceutical intermediate. | [Definition]
ChEBI: 3-amino-4-iodopyridine is an aminopyridine that is 3-aminopyridine carrying an additional iodo substituent at postion 4. It has a role as a Saccharomyces cerevisiae metabolite. It is an aminopyridine and an organoiodine compound. | [Synthesis]
General procedure for the synthesis of 3-amino-4-iodopyridine from N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide: N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide (20.00 g, 65.76 mmol) was placed in a 2 L round-bottomed flask, and 24% sulfuric acid aqueous solution (640 mL) was added. The mixture was carefully heated to 100 °C and kept for 4 hours. The progress of the reaction was monitored by analytical HPLC. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was slowly adjusted to 7-8 with 4 N NaOH solution (~700 mL).Subsequently, saturated sodium bicarbonate solution was added and extracted with dichloromethane (3 x 500 mL). The organic phases were combined and concentrated to give 3-amino-4-iodopyridine (13.3 g, 92% yield). | [References]
[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6519 - 6534
[2] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 154
[3] Patent: EP1595881, 2005, A1. Location in patent: Page/Page column 57
[4] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 11 - 16
[5] Tetrahedron Letters, 2004, vol. 45, # 46, p. 8569 - 8573 |
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