| Identification | More | [Name]
2-Naphthylhydrazine hydrochloride | [CAS]
2243-58-5 | [Synonyms]
2-HYDRAZINONAPHTHALENE
2-HYDRAZINONAPHTHALENE HYDROCHLORIDE
2-NAPHTHALENYL HYDRAZINE HYDROCHLORIDE
2-NAPHTHYLHYDRAINE HYDROCHLORIDE
2-NAPHTHYL HYDRAZINE
2-NAPHTHYLHYDRAZINE HYDROCHLORIDE
N'-NAPHTHALEN-2-YL-HYDRAZINE HCL
2-naphthylhydrazinium(1+) chloride
2-NaphthylhydrazineHCl
2-naphthylhydrazinium chloride
2-Hydrazinonaphthalene monohydrochloride
Naphthalen-2-yl-hydrazine hydrochloride | [Molecular Formula]
C10H11ClN2 | [MDL Number]
MFCD04109481 | [Molecular Weight]
194.66 | [MOL File]
2243-58-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
123°C | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White | [InChI]
InChI=1S/C10H10N2.ClH/c11-12-10-7-3-5-8-4-1-2-6-9(8)10;/h1-7,12H,11H2;1H | [InChIKey]
FYSSYOCJFZSKNW-UHFFFAOYSA-N | [SMILES]
NNC1=C2C(C=CC=C2)=CC=C1.[H]Cl | [CAS DataBase Reference]
2243-58-5(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow powder | [Uses]
2-Naphthylhydrazine Hydrochloride acts as a reagent in the synthesis and biological activity of some new pyrazoline and pyrimidine derivatives as antibacterial and antifungal agents. Synthesis and biological evaluation of 6-hydroxypyridazinone derivatives as σ1 receptor ligands for treating neuropathic pain. | [Synthesis]
2.1 Synthesis of 2-naphthylhydrazine hydrochloride
To a suspension of 2-naphthylamine (800 mg, 5.59 mmol) in hydrochloric acid (6.0 M, 6 mL), a solution of sodium nitrite (NaNO2, 578 mg, 8.38 mmol) in water (1.2 mL) was slowly added under cooling conditions in a water-ice bath (addition time was 2 min). The reaction mixture was stirred in a water-ice bath for 1 h, followed by the slow addition of stannous chloride (SnCl2, 3.71 g, 19.56 mmol) (addition time was 5 min). The resulting suspension was continued to be stirred in a water-ice bath for 3.5 h, followed by filtration. The filter cake was washed sequentially with ice water (0°C, 4 × 8 mL), room temperature water (1 × 8 mL), ice ether (0°C, 2 × 4 mL), and ether/hexane (1:1, 2 × 4 mL) and hexane (2 × 5 mL). The solid was dried to give 690 mg of the target product (Rf = 0.7, 40% ethyl acetate/hexane unfolding agent, milky white solid, 63% yield).
1H NMR (DMSO-d6, 250 MHz, δ): 7.81 (m, 2H, ArH), 7.71 (d, J = 7.7 Hz, 1H, ArH), 7.49-7.19 (m, 4H, ArH).
MS-El+ m/z: 159.1 (M-HCl+1). | [References]
[1] Patent: EP2395003, 2011, A1. Location in patent: Page/Page column 12; 17-18
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1714 - 1720
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 20, p. 5202 - 5205
[4] Angew. Chem., 2014, vol. 126, # 20, p. 5303 - 5306,4 |
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