Methyl 2-methylindazole-6-carboxylate
- Product Name
- Methyl 2-methylindazole-6-carboxylate
- CAS No.
- 1071433-01-6
- Chemical Name
- Methyl 2-methylindazole-6-carboxylate
- Synonyms
- -2H-indazoL;Methyl 2-methylindazole-6-carboxylate;Methyl 2-Methyl-2H-indazol-6-carboxylate;6-(Methoxycarbonyl)-2-methyl-2H-indazole;methyl 2-methyl-2H-indazole-6-carboxylate;2-Methyl-2H-indazole-6-carboxylic acid methyl ester;2H-Indazole-6-carboxylic acid, 2-methyl-, methyl ester;2-Methyl-2H-indazole-6-carboxylic acid methyl ester
- CBNumber
- CB52485606
- Molecular Formula
- C10H10N2O2
- Formula Weight
- 190.2
- MOL File
- 1071433-01-6.mol
Methyl 2-methylindazole-6-carboxylate Property
- Boiling point:
- 338.9±15.0 °C(Predicted)
- Density
- 1.23±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- form
- solid
- pka
- -0.39±0.30(Predicted)
- Appearance
- Off-white to light yellow Solid
Safety
- WGK Germany
- 3
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SYX00170
- Product name
- 2-Methyl-2H-indazole-6-carboxylic acid methyl ester
- Purity
- Aldrich
- Packaging
- 1g
- Price
- $639
- Updated
- 2025/07/31
- Product number
- M321240
- Product name
- 2-Methyl-2H-indazole-6-carboxylic acid methyl ester
- Packaging
- 5g
- Price
- $1260
- Updated
- 2021/12/16
- Product number
- Y5165
- Product name
- Methyl2-methyl-2H-indazole-6-carboxylate
- Packaging
- 10g
- Price
- $1051
- Updated
- 2021/12/16
- Product number
- 47556
- Product name
- 2-Methyl-2H-indazole-6-carboxylic acid methyl ester
- Packaging
- 5G
- Price
- $2200
- Updated
- 2021/12/16
- Product number
- CHM0392967
- Product name
- METHYL-2-METHYL-2H-INDAZOLE-6-CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $500.56
- Updated
- 2021/12/16
Methyl 2-methylindazole-6-carboxylate Chemical Properties,Usage,Production
Uses
2-Methyl-2H-indazole-6-carboxylic Acid Methyl Ester is a useful synthetic intermediate. It is an analog of Indazole-3-carboxylic Acid Methyl Ester (I505250) which has potential as application of N-benzoylindazole derivatives and analogues as inhibitors of human neutrophil elastase. Indazole-3-carboxylic Acid Methyl Ester (I505250) is also used in the preparation of indazole-pyridine based protain kinase/Akt inhibitors.
Synthesis
170487-40-8
74-88-4
1007219-73-9
1071433-01-6
Sodium hydride (60% dispersed in mineral oil, 154 mg, 3.85 mmol) was added batchwise to an anhydrous tetrahydrofuran solution of methyl 1H-indazole-6-carboxylate (566 mg, 3.21 mmol) under cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 30 min. Subsequently, iodomethane (547 mg, 3.85 mmol) was slowly added dropwise and the reaction was continued with stirring at room temperature overnight. Upon completion of the reaction, the mixture was cooled to 0 °C, the reaction was quenched by careful addition of water and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography afforded methyl 1-methyl-1H-indazole-6-carboxylate (130 mg) and methyl 2-methyl-2H-indazole-6-carboxylate (230 mg) in 59% overall yield. The structures of the products were confirmed by 1H NMR: 1-methyl-1H-indazole-6-carboxylic acid methyl ester: 1H NMR (400 MHz, CDCl3) δ 3.97 (3H, s), 4.14 (3H, s), 7.74-7.82 (2H, m), 8.02 (1H, s), 8.17 (1H, d, J = 0.8 Hz). 2-methyl-2H-indazole- 6-carboxylic acid methyl ester: 1H NMR (400 MHz, CDCl3) δ 3.94 (3H, s), 4.25 (3H, s), 7.65-7.72 (2H, m), 7.92 (1H, s), 8.47 (1H, d, J = 1.2 Hz). Mass spectral analysis: [M + H]+ m/z 191.0815 (calculated value C10H11N2O2, 191.0816).
References
[1] Patent: WO2014/89364, 2014, A1. Location in patent: Paragraph 00477; 00478
Methyl 2-methylindazole-6-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
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