| Identification | More | [Name]
4-Iodopyrazole | [CAS]
3469-69-0 | [Synonyms]
1H-PYRAZOLE, 4-IODO-
4-IODO-1H-PYRAZOLE
4-IODOPYRAZOLE
4-IODOPYRAZOLE 99%
4-Iodopyrazole ,98% | [EINECS(EC#)]
222-434-1 | [Molecular Formula]
C3H3IN2 | [MDL Number]
MFCD00005244 | [Molecular Weight]
193.97 | [MOL File]
3469-69-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
108-110 °C (lit.) | [Boiling point ]
291.9±13.0 °C(Predicted) | [density ]
2.335±0.06 g/cm3(Predicted) | [RTECS ]
UQ7145000 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
12.99±0.50(Predicted) | [color ]
White to off-white | [Water Solubility ]
Soluble in water. | [Sensitive ]
Light Sensitive | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C3H3IN2/c4-3-1-5-6-2-3/h1-2H,(H,5,6) | [InChIKey]
LLNQWPTUJJYTTE-UHFFFAOYSA-N | [SMILES]
N1C=C(I)C=N1 | [CAS DataBase Reference]
3469-69-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
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 . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29331900 |
| Hazard Information | Back Directory | [Chemical Properties]
White or off-white solid | [Uses]
4-Iodopyrazole is used in the synthesis of (pyrazolyl)oxobenzocycloheptapyridinyl acetamides that act as inhibitors of c-Met. | [Definition]
ChEBI:4-iodopyrazole is a member of pyrazoles and an organoiodine compound. | [General Description]
4-Iodopyrazole is a valuable intermediate for the synthesis of biologically active compounds. It undergoes iodination in the presence of iodine and ammonium hydroxide to yield 3,4-di-iodo- and 3,4,5-tri-iodo-pyrazole. | [Synthesis]
The general procedure for the synthesis of 4-iodopyrazole from pyrazole is as follows:
Example 1: Preparation of 2-amino-3-methyl-5-(1-methyl-1H-pyrazol-4-yl)-5-(3-pyrimidin-5-ylphenyl)-3,5-dihydro-4H-imidazol-4-one
Step a): Preparation of compound 2
A mixture of pyrazole (3.00 g, 44.0 mmol), iodine (6.71 g, 26.4 mmol) and ceric ammonium nitrate (14.5 g, 26.4 mmol) in acetonitrile (400 mL) was stirred at room temperature for 2.5 hours. Upon completion of the reaction, the mixture was concentrated and partitioned between ethyl acetate (250 mL) and 5% aqueous sodium bisulfite (250 mL). After addition of water (150 mL), the organic layer was separated, washed with brine (250 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to afford compound 2 (7.80 g, 91% yield) as a white solid with a melting point of 105-108 °C.
1H NMR (300 MHz, CDCl3) δ 7.63 (s, 2H). | [References]
[1] Tetrahedron Letters, 2001, vol. 42, # 5, p. 863 - 865
[2] Heterocycles, 2003, vol. 60, # 4, p. 879 - 886
[3] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8075 - 8079
[4] Tetrahedron Letters, 2001, vol. 42, # 11, p. 2089 - 2092
[5] Russian Chemical Bulletin, 2014, vol. 63, # 2, p. 360 - 367 |
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