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Published TCIMAIL newest issue No.199
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CAS RN: 6638-79-5 | Product Number: D1899
N,O-Dimethylhydroxylamine Hydrochloride
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Purity: >98.0%(T)
Synonyms:
- N-Methoxy-N-methylamine Hydrochloride
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
Shipping Information
|
|---|---|---|---|---|---|
| 25G |
£44.00
|
8 | ≥100 |
|
|
| 100G |
£120.00
|
4 | ≥60 |
|
|
| 500G |
£385.00
|
1 | ≥60 |
|
* Stock available in Belgium: Shipment on the same day
* Stock available in Japan: Please check the Shipping Simulation for estimated shipments. (excludes regulated items and dry ice shipments)
| Product Number | D1899 |
Purity / Analysis Method 
|
>98.0%(T) |
| Molecular Formula / Molecular Weight | C__2H__7NO·HCl = 97.54 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Hygroscopic |
| CAS RN | 6638-79-5 |
| Reaxys Registry Number | 3650353 |
| PubChem Substance ID | 87568359 |
| MDL Number | MFCD00012485 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(Neutralization titration) | min. 98.0 % |
| Melting point | 114.0 to 118.0 °C |
Properties (reference)
| Melting Point | 115 °C |
| Solubility in water | Soluble |
GHS
| Pictogram |
|
| Signal Word | Warning |
| Hazard Statements | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| Precautionary Statements | 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. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. |
Related Laws:
| EC Number | 229-642-1 |
Transport Information:
| HS Number | 2928009090 |
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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Documents
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