Name | 3-Methyl-6-nitroindazole |
Synonyms | 3-Methyl-6-nitroindole 3-Methyl-6-nitroindazole 3-Methyl-6-Nitro-1h-Indole 3-METHYL-6-NITRO-1H-INDOZOLE 3-Methyl-6-nitro-1H-indaz... 3-Methyl-6-nitro-1H-indazole 3-Methyl-6-nitro-2H-indazole 3-Methyl-6-Nifro-1H-Indazole 3-METHYL-6-NIFRO-1H-INDAZOLE 3-methyl-6-nitro-3H-indazole 3-Methyl-6-Nitro-1H-Indozole |
CAS | 6494-19-5 |
EINECS | 613-731-0 |
InChI | InChI=1/C8H7N3O2/c1-5-7-3-2-6(11(12)13)4-8(7)10-9-5/h2-5H,1H3 |
Molecular Formula | C8H7N3O2 |
Molar Mass | 177.16 |
Density | 1.437 |
Melting Point | 187-188°C |
Boling Point | 384.9±22.0 °C(Predicted) |
Flash Point | 122.8°C |
Solubility | Chloroform (Slightly), Methanol (Slightly) |
Vapor Presure | 0.00684mmHg at 25°C |
Appearance | Solid |
Color | Beige to Dark Yellow |
pKa | 11.47±0.40(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.704 |
MDL | MFCD07082704 |
Risk Codes | 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
Safety Description | S24/25 - Avoid contact with skin and eyes. S36/37 - Wear suitable protective clothing and gloves. |
HS Code | 29339900 |
Application | 3-methyl-6-nitro-1h-indazole is an important intermediate of patent drug pazopanib, pazopanib, a novel oral angiogenesis inhibitor developed by GlaxoSmithKline, interferes with the new angiogenesis required for survival and growth of recalcitrant tumors, targeting the vascular endothelial growth factor receptor (VEGFR) acts by inhibiting the generation of new blood vessels that supply the tumor. |
preparation | the method of synthesizing 3-methyl-6-nitro-1h-indazole in a microchannel reactor is carried out according to the following steps: Step 1, the 2-ethyl-5-nitroaniline is dissolved in acetic acid to prepare a mass concentration of 22% solution and a mass concentration of 30% sodium nitrite aqueous solution as reaction materials, the reaction material is passed into each straight channel module in the microchannel reactor by the metering pump for preheating, and the molar ratio of 2-ethyl-5-nitroaniline to sodium nitrite is controlled by the flow rate = 1:1.3, control 2-ethyl-5-nitroaniline acetic acid solution flow rate: 20mL/min, control sodium nitrite aqueous solution flow rate: 6.2/min, the acetic acid solution of 2-ethyl-5-nitroaniline is driven into the preheating module of the first microchannel module, and the temperature is controlled at 45 ℃; the acetic acid solution and the sodium nitrite solution of 2-ethyl-5-nitroaniline are respectively pumped into the second mixing module of the micro-mixer with respective metering pumps for mixing, through a series of enhanced mass transfer type Micro Channel Module and DC type Micro Channel Module, after the reaction process is completed, the reaction temperature is 45 degrees C, the reaction residence time is 90s The product flows out from the outlet of the reactor; Step 3. The product is then pre-cooled to 10 °c, then added to ice water under stirring, filtered, and the filter cake is washed with ice water, it was added to toluene for 1 hour, washed twice with toluene, and then dried to obtain 3-methyl-6-nitro-1h-indazole as a bright yellow solid. |