Cyclopentylhydrazine hydrochloride CAS 24214-72-0
Cyclopentylhydrazine hydrochloride Basic information
| Product Name: | Cyclopentylhydrazine hydrochloride |
| Synonyms: | 1-CYCLOPENTYHYDRAZINE HYDROCHLORIDE;1-CYCLOPENTYLHYDRAZINE HYDROCHLORIDE;CYCLOPENTYL HYDRAZINE HYDROCHLORIDE;CyclopentylhydrazineHCl;Hydrazinocyclopentane hydrochloride;cyclopentylhydrazine, HCl salt;cyclopentyl-hydrazinhydrochloride;CYCLOPENTYLHYDRAZINE;HYDRON;CHLORIDE |
| CAS: | 24214-72-0 |
| MF: | C5H13ClN2 |
| MW: | 136.62 |
| EINECS: | |
| Product Categories: | Ring Systems |
| Mol File: | 24214-72-0.mol |
Cyclopentylhydrazine hydrochloride Chemical Properties
| Melting point | 131-132 °C |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| form | Powder |
| Appearance | White to off-white Solid |
| InChI | InChI=1S/C5H12N2.ClH/c6-7-5-3-1-2-4-5;/h5,7H,1-4,6H2;1H |
| InChIKey | GONHTJWVIZVBOU-UHFFFAOYSA-N |
| SMILES | C1(NN)CCCC1.Cl |
Safety Information
| Hazard Codes | Xi |
| Hazard Note | Irritant |
| HS Code | 2928009090 |
| Uses | Cyclopentylhydrazine Hydrochloride |
| Synthesis | 79201-39-1 24214-72-0 Step 2: Synthesis of cyclopentylhydrazine hydrochlorideTert-butyl N'-cyclopentylidenehydrazine formate (5.448 g, 27.48 mmol) was dissolved in a solvent mixture of anhydrous tetrahydrofuran (25 mL) and anhydrous methanol (34 mL). Under argon protection, sodium cyanoborohydride (2.044 g, 32.53 mmol) was added in batches, followed by refluxing the reaction mixture for 10 min. Upon completion of the reaction, it was cooled to room temperature, 6N hydrochloric acid (12 mL) was added, and refluxing was continued for 1.5 hours. An aliquot was analyzed by NMR and it was confirmed that some of the BOC protecting groups were still not removed. Add 6N hydrochloric acid and continue refluxing for 3 hours. At the end of the reaction, cooled to room temperature and stirred overnight. The insoluble material was removed by filtration, and the filtrate was concentrated and azeotropized with toluene three times to completely remove the water. The residue was dissolved in hot isopropanol, cooled to room temperature, diluted with ether and further cooled. The solid was collected by filtration to afford cyclopentylhydrazine hydrochloride (3.903 g, 103% yield), which could be used in subsequent reactions without further purification. |
| References | [1] Patent: US2007/225280, 2007, A1. Location in patent: Page/Page column 48 [2] Patent: WO2014/16789, 2014, A1. Location in patent: Page/Page column 18; 19 [3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 2, p. 393 - 404 [4] Journal of Organic Chemistry, 1981, vol. 46, # 26, p. 5413 - 5414 [5] Patent: US2004/220186, 2004, A1. Location in patent: Page 19 |
Cyclopentylhydrazine hydrochloride Preparation Products And Raw materials
| Raw materials | Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI)-->Sodium cyanoborohydride-->Water-->Tetrahydrofuran-->Methanol-->Hydrochloric acid |
| Preparation Products | 2-CYCLOPENTYL-5-METHYL-2H-PYRAZOL-3-YLAMINE |
