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CAS RN: 6638-79-5 | 產品號碼: D1899
N,O-Dimethylhydroxylamine Hydrochloride
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產品規格
| Appearance | White to Almost white powder to crystal |
| Purity(Neutralization titration) | min. 98.0 % |
| Melting point | 114.0 to 118.0 °C |
性質
| 熔點 | 115 °C |
| 水溶性 | Soluble |
GHS
| 圖形表示 |
|
| 信號詞 | Warning |
| 危險性說明 | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| 防範說明 | P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. |
相關法規
運輸資料
| HS編碼* | 2928.00-000 |
Application
TCI Practical Example: Preparation of Weinreb Amide Using N,O-dimethylhydroxylamine Hydrochloride
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Used Chemicals
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- N,O-Dimethylhydroxylamine Hydrochloride [D1899]
- Acryloyl Chloride
- Sodium Hydrogen Carbonate [S0561]
- Dichloromethane
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Procedure
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N,O-Dimethylhydroxylamine hydrochloride (646.7 mg, 6.63 mmol, 1.2 eq.) was added to a solution of acryloyl chloride (0.45 mL, 500 mg, 5.52 mmol) and NaHCO3 (1.16 g, 13.8 mmol, 2.5 eq.) in dry dichloromethane (4.6 mL) at 0 °C. The mixture was stirred for overnight at room temperature. The reaction mixture was quenched with 3 mol/L HCl (10 mL) and the two layers were separated. The organic layer was washed with sat. NaHCO3 aq. (10 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the Weinreb amide 1 as a colorless liquid (413 mg, 65% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.55).
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Analytical Data
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Weinreb amide 1
1H NMR (270 MHz, CDCl3); δ 6.74 (dd, J = 10.1, 17.1 Hz, 1H), 6.43 (dd, J = 2.3, 17.1 Hz, 1H), 5.76 (dd, J = 2.3, 10.1 Hz, 1H), 3.71 (s, 3H), 3.27 (s, 3H).
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Other Reference
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- Concise stereoselective and stereodivergent syntheses of (±)-melicolones A and B
- S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815.
- O. P. Goel, U. Krolls, M. Stier, S. Kesten, Org. Synth. Coll. 1993, 8, 68.; 1989, 67, 69.
- M. P. Sibi, Org. Prep. Proced. Int. 1993, 25, 15. (review)
- V. K. Khlestkin, D. G. Mazhukin, Curr. Org. Chem. 2003, 7, 967. (review)
Application
Weinreb Ketone Synthesis
Typical procedure (Preparation of Weinreb’s amides from acid chlorides): Acid chloride (1 mmol) and N,O-dimethylhydroxylamine hydrochloride (110mg, 1.1 mmol) are dissolved in ethanol-free chloroform (10 mL) at room temperature. The solution is cooled to 0 °C and pyridine (185 mg, 2.2 mmol) is added. The mixture is stirred at rt for 1 h and evaporated in vacuo. The residue is dissolved in a 1:1 mixture of diethylether and methylene chloride, and washed with brine. The organic layer is dried over anhydrous sodium sulfate and concentrated to give the Weinreb’s amide which is purified by silica gel chromatography or by distillation.
References
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