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Published TCIMAIL newest issue No.197
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CAS RN: 563-41-7 | Product Number: S0032
Semicarbazide Hydrochloride
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Purity: >99.0%(T)
Synonyms:
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 25G |
€16.00
|
3 | 29 |
|
| 500G |
€85.00
|
1 | ≥100 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | S0032 |
| Purity / Analysis Method | >99.0%(T) |
| Molecular Formula / Molecular Weight | CH__5N__3O·HCl = 111.53 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| CAS RN | 563-41-7 |
| Reaxys Registry Number | 3593642 |
| PubChem Substance ID | 87575661 |
| Merck Index (14) | 8444 |
| MDL Number | MFCD00013009 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(Bromination Method) | min. 99.0 % |
Properties (reference)
| Solubility (slightly sol. in) | Alcohol |
| Solubility (insoluble in) | Ether |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H301 : Toxic if swallowed. H315 : Causes skin irritation. H319 : Causes serious eye irritation. H361 : Suspected of damaging fertility or the unborn child. H373 : May cause damage to organs through prolonged or repeated exposure. |
| Precautionary Statements | P260 : Do not breathe dust. P201 : Obtain special instructions before use. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P308 + P313 : IF exposed or concerned: Get medical advice/ attention. P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth. |
Related Laws:
| EC Number | 209-247-0 |
| RTECS# | VT3500000 |
Transport Information:
| UN Number | UN2811 |
| Class | 6.1 |
| Packing Group | III |
| HS Number | 2928009090 |
Application
Synthesis of Alkynyl Ketones using Eschenmoser-Tanabe Fragmentation(alternative method)
Typical Procedure:
To a stirred solution of semicarbazide hydrochloride (12.94 g, 116.0 mmol) and sodium acetate trihydrate (0.95 g, 12 mmol) in water (116 mL) is added 1 (2.63 g, 11.6 mmol) at room temperature. Sufficient 95% ethanol is added to bring about a homogenous solution. After stirring at room temperature for 7 h, the reaction mixture is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (ethyl acetate → ethyl acetate : methanol = 9 : 1) to give 2 (2.92 g, 89%) as a white solid.
Next, to a stirred solution of 2 (1.86 g, 6.57 mmol) in dichloromethane (65.7 mL) is added portionwise 95% lead tetraacetate (6.42 g, 13.8 mmol), maintaining the bath temperature at –10 °C After stirring for 1 h at –10 °C, ethyl acetate is added to the reaction mixture, which is allowed to warm to room temperature. Then the mixture is filtered through a Celite pad and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography (hexane : ethyl acetate = 4 : 1) to give 3 (0.83 g, 60%) as a colorless oil.
To a stirred solution of semicarbazide hydrochloride (12.94 g, 116.0 mmol) and sodium acetate trihydrate (0.95 g, 12 mmol) in water (116 mL) is added 1 (2.63 g, 11.6 mmol) at room temperature. Sufficient 95% ethanol is added to bring about a homogenous solution. After stirring at room temperature for 7 h, the reaction mixture is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (ethyl acetate → ethyl acetate : methanol = 9 : 1) to give 2 (2.92 g, 89%) as a white solid.
Next, to a stirred solution of 2 (1.86 g, 6.57 mmol) in dichloromethane (65.7 mL) is added portionwise 95% lead tetraacetate (6.42 g, 13.8 mmol), maintaining the bath temperature at –10 °C After stirring for 1 h at –10 °C, ethyl acetate is added to the reaction mixture, which is allowed to warm to room temperature. Then the mixture is filtered through a Celite pad and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography (hexane : ethyl acetate = 4 : 1) to give 3 (0.83 g, 60%) as a colorless oil.
References
- 1)Thermolysis of Δ3-1 ,3,4-oxadiazolin-2-ones and 2-phenylimino-Δ3-l,3,4-oxadiazolinesderived from α,β-epoxyketones. An alternative method for the conversion of α,β-epoxyketones to alkynones and alkynals
- 2)Total Synthesis of (–)-Mersicarpine
PubMed Literature
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