| Identification | Back Directory | [Name]
2,3-DIMETHYL-6-NITRO-2H-INDAZOLE | [CAS]
444731-73-1 | [Synonyms]
Pazopanib Impurity 19
3-Methly-6-nitroindazole
2,3-dimethyl-6-nitrobazole
2,3-Dimethyl-6-nitro-1H-i...
2,3-dimethyl-6-nitro-indazole
3-diMethyl-6-nitro-2H-indazole
2,3-DIMETHYL-6-NITRO-2H-INDAZOLE
2,3-dimethyl-6-nitro-1H-indazole
2H-Indazole, 2,3-diMethyl-6-nitro-
2,3-DIMETHYL-6-NITRO-2H-INDAZOLE ISO 9001：2015 REACH | [EINECS(EC#)]
610-189-7 | [Molecular Formula]
C9H9N3O2 | [MDL Number]
MFCD10703326 | [MOL File]
444731-73-1.mol | [Molecular Weight]
191.19 |
| Chemical Properties | Back Directory | [Melting point ]
183-186°C | [Boiling point ]
377.0±22.0 °C(Predicted) | [density ]
1.36±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-0.55±0.30(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C9H9N3O2/c1-6-8-4-3-7(12(13)14)5-9(8)10-11(6)2/h3-5H,1-2H3 | [InChIKey]
JHGRUPGVUMAQQU-UHFFFAOYSA-N | [SMILES]
N1=C2C(C=CC([N+]([O-])=O)=C2)=C(C)N1C |
| Hazard Information | Back Directory | [Uses]
2,3-Dimethyl-6-nitro-2H-indazole is an impurity in the synthesis of Pazopanib (P210925) hydrochloride, an oral angiogenesis inhibitor targeting VEGFR and PDGFR. | [Synthesis]
General procedure for the synthesis of 2,3-dimethyl-6-nitroindazole (2a) from 3-methyl-6-nitro-1H-indazole (1a, 10.00 g, 56 mmol) and dimethyl carbonate (DMC, 6.04 g, 67 mmol): first, 3-methyl-6-nitro-1H-indazole and triethylenediamine (DABCO, 6.40 g, 56 mmol) were dissolved in 100 mL of N,N-dimethylformamide (DMF). The reaction mixture was stirred at room temperature for 15 min, followed by slow dropwise addition of dimethyl carbonate. After the dropwise addition, the reaction system was heated to reflux temperature with continuous stirring for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 120 mL of water was added and stirred for 15 minutes, at which time a large amount of light yellow solid precipitated. The solid product was collected by filtration and dried to give 2,3-dimethyl-6-nitroindazole (2a, 8.66 g, 81.1% yield). The melting point of the product was 187~187.6 °C. 1H NMR (400 MHz, DMSO-d6) δ: 2.67 (s, 3H), 4.14 (s, 3H), 7.73 (d, J = 9.2 Hz, 1H), 7.93 (d, J = 8.8 Hz, 1H), 8.51 (s, 1H). | [structure and hydrogen bonding]
In the mol-ecule of 2,3-dimethyl-6-nitro-2H-indazole, C9H9N3O2, the indazole ring system is almost planar [maximum deviation = 0.019 (3) Å for the C atom bearing the nitro group]. In the crystal structure, inter-molecular C—H...O inter-actions link the mol-ecules into centrosymmetric dimers, forming R 2 2(18) ring motifs. Aromatic π–π contacts between indazole rings [centroid–centroid distances = 3.632 (1) and 3.705 (1)?] may further stabilize the structure[1].
| [References]
[1] Yan Chen, Ping Wei, Zheng Fang. “2,3-Dimethyl-6-nitro-2H-indazole.” Acta crystallographica. Section E, Structure reports online 65 Pt 8 (2009): o1775.
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