ChemicalBook > CAS DataBase List > Methyl 2-methylindazole-6-carboxylate

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
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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
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Safety

WGK Germany 
3
HS Code 
2933998090
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SYX00170
Product name
2-Methyl-2H-indazole-6-carboxylic acid methyl ester
Purity
Aldrich
Packaging
1g
Price
$639
Updated
2025/07/31
TRC
Product number
M321240
Product name
2-Methyl-2H-indazole-6-carboxylic acid methyl ester
Packaging
5g
Price
$1260
Updated
2021/12/16
Apolloscientific
Product number
OR30724
Product name
Methyl 2-methyl-2H-indazole-6-carboxylate
Packaging
1g
Price
$71
Updated
2021/12/16
SynQuest Laboratories
Product number
4H23-1-Q9
Product name
Methyl 2-methyl-2H-indazole-6-carboxylate
Packaging
1g
Price
$84
Updated
2021/12/16
Apolloscientific
Product number
OR30724
Product name
Methyl 2-methyl-2H-indazole-6-carboxylate
Packaging
5g
Price
$254
Updated
2021/12/16
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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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Methyl 2-methylindazole-6-carboxylate Suppliers

Synthonix Inc
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Matrix Scientific
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American Custom Chemicals Corporation
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1071433-01-6, Methyl 2-methylindazole-6-carboxylateRelated Search:


  • 6-(Methoxycarbonyl)-2-methyl-2H-indazole
  • Methyl 2-Methyl-2H-indazol-6-carboxylate
  • 2-Methyl-2H-indazole-6-carboxylic acid methyl ester
  • Methyl 2-methylindazole-6-carboxylate
  • methyl 2-methyl-2H-indazole-6-carboxylate
  • 2H-Indazole-6-carboxylic acid, 2-methyl-, methyl ester
  • -2H-indazoL
  • 2-Methyl-2<i>H</i>-indazole-6-carboxylic acid methyl ester
  • 1071433-01-6