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| | 6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Basic information |
| Product Name: | 6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid | | Synonyms: | 6-[2-[(tert-Butoxy)carbonyl]hydrazinyl]-3-pyridinecarboxylic acid;6-Boc-Hydrazynonicotinic acid;6-Boc-hydrazinonicotinic acid;6-({[(tert-butoxy)carbonyl]aMino}aMino)pyridine-3-carboxylic acid;6-(2-(tert-Butoxycarbonyl)hydrazono)-1,6-dihydropyridine-3-carboxylic acid;6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid
6-[2-[(tert-Butoxy)carbonyl]hydrazinyl]-3-pyridinecarboxylic acid;3-Pyridinecarboxylicacid, 6-[1-[(1,1-dimethylethoxy)carbonyl]hydrazinyl]-;6-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]pyridine-3-carboxylic acid | | CAS: | 133081-25-1 | | MF: | C11H15N3O4 | | MW: | 253.25 | | EINECS: | | | Product Categories: | | | Mol File: | 133081-25-1.mol | ![6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Structure](CAS/GIF/133081-25-1.gif) |
| | 6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Chemical Properties |
| Melting point | 126 °C | | density | 1.312 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 2.61±0.10(Predicted) | | form | Solid | | color | White to Off-White |
| | 6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Usage And Synthesis |
| Uses |
6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.
| | Synthesis | Di-tert-butyl dicarbonate (0.40 g, 1.82 mmol) was added to an N,N-dimethylformamide (DMF) solution of 6-hydrazinylpyridine-3-carboxylic acid (0.346 g, 1.82 mmol) and triethylamine (0.32 mL, 2.36 mmol). The reaction mixture was stirred at 25 °C for 1 h to become homogeneous, and stirring was continued for 16 h. The reaction was carried out under reduced pressure. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with a solvent mixture of ethyl acetate/methanol (4:1, v/v) and purified by silica gel column chromatography, using ethyl acetate as eluent, to afford 6-[2-(tert-butoxycarbonyl)hydrazinyl]nicotinic acid (4b) as a light yellow solid (0.44 g, 96% yield).IR (ATR, cm-1): 3353, 3227, 2975, 1719, 1593, 1472, 1372, 1256, 1014, 867, 794, 520. 1H NMR (DMSO-d6, δ): 12.584 (s, 1H), 8.59 (s, 1H), 7.97 (d, J = 9 Hz, 1H), 6.54 (d, J = 9 Hz, 1H). 13C NMR (DMSO-d6, δ): 166.6 , 155.7, 150.5, 138.5, 116.7, 79.3, 28.1, 14.0. MS (ESI-): [M-H]- m/z 252.00. MS (ESI+): [M+H]+ m/z 254.07. HRMS (ESI+): [M+H]+ m/z 254.1145 (calculated values) C11H16N3O4, 254.1141). | | References | [1] Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 208 - 214
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4764 - 4767
[3] Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 951 - 959
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 68 - 76
[5] Pharmazie, 2006, vol. 61, # 4, p. 269 - 273 |
| | 6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Preparation Products And Raw materials |
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