| Identification | More | [Name]
1-Methylindazole-3-carboxylic acid | [CAS]
50890-83-0 | [Synonyms]
1-METHYL-1H-INDAZOLE-3-CARBOXYLIC ACID
1-METHYL-3-INDAZOLECARBOXYLIC ACID
1-METHYLINDAZOLE-3-CARBOXYLIC ACID
1-METHYL-INDAZOLE-CARBOXYLIC-ACID
AKOS BB-9979
N-METHYL-(1H)INDAZOLE-3-CARBOXYLIC ACID
N-METHYL-INDAZOLE-3-CARBOXYLIC ACID
N-METHYL-INDOZOLE-3-CARBOXYLIC ACID
TIMTEC-BB SBB000193
1-chloro-2-methyl-4-nitrobenzene
1-MethylIndazoleCarboxylicAcid(ForGranisetronHcl)
1-methylindazole-3-carboxylic acid (intermediate of granisetron)
1H-INDAZOLE-3-CARBOXYLIC ACID, 1-METHYL-
MIC(1-methyl-indozole-3-carboxylicacid)
METHYL-INDOZOLE-3-CARBOXYLIC ACID
1-Methylindazole-3-carboxylic acid ,98% | [EINECS(EC#)]
626-233-3 | [Molecular Formula]
C9H8N2O2 | [MDL Number]
MFCD00272569 | [Molecular Weight]
176.17 | [MOL File]
50890-83-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
213 °C | [Boiling point ]
383.7±15.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.14±0.10(Predicted) | [color ]
White to Off White | [Water Solubility ]
Insoluble in water. Soluble in DMSO and Methanol. | [Detection Methods]
T,NMR | [InChI]
InChI=1S/C9H8N2O2/c1-11-7-5-3-2-4-6(7)8(10-11)9(12)13/h2-5H,1H3,(H,12,13) | [InChIKey]
OVVDFORZEGKEJM-UHFFFAOYSA-N | [SMILES]
N1(C)C2=C(C=CC=C2)C(C(O)=O)=N1 | [CAS DataBase Reference]
50890-83-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Off White Solid | [Uses]
1-Methylindazole-3-carboxylic acid is used as important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used as a pharmaceutical adjuvant, Granisetron Impurity D. | [Uses]
Granisetron Impurity D.
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 63, p. 8448, 1998 DOI: 10.1021/jo981557o | [Synthesis]
Calcium oxide (7.0 g, 0.124 mol, 2.0 molar equiv.) was added to technical methanol (150 ml), and the mixture was heated under reflux for 2 hours in a nitrogen atmosphere Indazole-3-carboxylic acid (10 g, 0.062 mol) was then added, and the reflux was continued for 2 hours. Dimethyl sulfate (15.6 g, 11.8 ml, 0.124 mole, 2.0 molar equiv.) was added dropwise under reflux for 2 hours, and the reflux continued for 2 hours. Water (100 ml) and 46% aqueous sodium hydroxide solution were added to produce a pH of about 14. Then, conc. hydrochloric acid was added to the reaction mixture to produce a pH of about 4. Calcium sulfate was collected by filtration and washed on a filter with hot methanol (3×30 ml). The methanol was removed under reduced pressure from the filtrate. The residuary mixture was stirred vigorously for 6 hours with a controlled pH of about 4. The solid product was collected by filtration, washed with water (3×30 ml), and dried in an oven at 50° C. overnight to give crude 1-Methylindazole-3-carboxylic acid. | [Purification Methods]
The crude 1-Methylindazole-3-carboxylic acid (1-MICA) (10.4 g) was treated by slurry in a methanol-water (3:7) mixture heated under reflux for 4 hours. The suspension was cooled to room temperature, and the solid product was collected by filtration, washed with the methanol-water (3:7) mixture (3×10 ml), and dried in an oven at 50° C. overnight to give pure 1-MICA (9.3 g, 85.6% yield, purity by HPLC: 99.70%).
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