| Identification | Back Directory | [Name]
3-Chloro-6-iodopyridazine | [CAS]
135034-10-5 | [Synonyms]
SW-116
SWF-116
3-Chloro-6-pyrazine
3-Chloro-6-iodopyridazine
3-Chloro-6-iodo-1,2-diazine
Pyridazine, 3-chloro-6-iodo-
3-Chloro-6-iodopyridazine,97%
3-Chloro-6-iodopyridazine ISO 9001：2015 REACH
3-Chloro-6-iodopyridazine Pyridazine, 3-chloro-6-iodo- | [Molecular Formula]
C4H2ClIN2 | [MDL Number]
MFCD08275187 | [MOL File]
135034-10-5.mol | [Molecular Weight]
240.43 |
| Chemical Properties | Back Directory | [Melting point ]
118-120° | [Boiling point ]
327.7±22.0 °C(Predicted) | [density ]
2.187±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Solid | [pka]
-1.18±0.10(Predicted) | [Appearance]
White to light brown Solid | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C4H2ClIN2/c5-3-1-2-4(6)8-7-3/h1-2H | [InChIKey]
PNEPCDPKMXJYIQ-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NN=C(I)C=C1 |
| Hazard Information | Back Directory | [Uses]
3-Chloro-6-iodopyridazine is a reactant in the Suzuki-Miyaura coupling reaction as well as a reactant in the synthesis of 6-Chloropyridazine-3-carbonitrile (C368635). | [Synthesis]
The general procedure for the synthesis of 3-chloro-6-iodopyridazine from 3,6-dichloropyridazine was as follows: the intermediate (E)-3-{3-[3'-(1-adamantyl)-4'-hydroxyphenyl]-6-pyridazinyl}-2-propenoic acid ethyl ester was prepared as follows. a) Synthesis of 3-chloro-6-iodopyridazine. Followed the method reported in the literature (Goodman, A.J. et al., Tetrahedron, 1999, 55, 15067-15070). A suspension of 3,6-dichloropyridazine (5.000 g, 33.56 mmol), NaI (6.75 g, 45.0 mmol), and HI (55% to 58%, 25 mL) was stirred for 23 h at 44 °C (oil bath) under argon protection. After completion of the reaction, the mixture was cooled to room temperature and quenched with concentrated HCl. Subsequently, the pH was adjusted to 12 with NaOH, stirred for 10 min and extracted with CH2Cl2. The organic phase was washed with water and dried. The solvent was removed under reduced pressure to give 7.96 g (98% yield) of 3-chloro-6-iodopyridazine as a light yellow solid with a melting point of 114-116 °C (literature value: 110-112 °C). 1H NMR (CDCl3) δ 7.23 (d, J = 8.7 Hz, 1H, 4-ArH), 7.84 ppm (d, J = 8.7 Hz, 1H, 5-ArH). | [References]
[1] Patent: US2010/4443, 2010, A1. Location in patent: Page/Page column 34
[2] Patent: WO2011/79305, 2011, A1. Location in patent: Page/Page column 41
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3793 - 3816
[4] Tetrahedron, 1999, vol. 55, # 52, p. 15067 - 15070
[5] Patent: US2005/234046, 2005, A1. Location in patent: Page/Page column 66 |
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