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Published TCIMAIL newest issue No.198
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CAS RN: 29684-56-8 | Product Number: M1279
(Methoxycarbonylsulfamoyl)triethylammonium Hydroxide Inner Salt
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Purity: >97.0%(N)
Synonyms:
- Burgess Reagent
- Methyl N-(Triethylammoniosulfonyl)carbamate
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 1G |
38,00 €
|
3 | ≥40 |
|
| 5G |
122,00 €
|
7 | ≥100 |
|
| 25G |
442,00 €
|
2 | 16 |
|
*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 | M1279 |
Purity / Analysis Method 
|
>97.0%(N) |
| Molecular Formula / Molecular Weight | C__8H__1__8N__2O__4S = 238.30 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive,Heat Sensitive |
| Packaging and Container
|
1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 29684-56-8 |
| Reaxys Registry Number | 1432131 |
| PubChem Substance ID | 87573236 |
| Merck Index (14) | 1502 |
| MDL Number | MFCD00077815 |
Specifications
| Appearance | White to Light yellow to Light orange powder to crystal |
| Purity(with Total Nitrogen) | min. 97.0 % |
| Melting point | 74.0 to 80.0 °C |
| NMR | confirm to structure |
Properties (reference)
| Melting Point | 79 °C |
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:
Transport Information:
| HS Number | 2935909099 |
Application
Preparation of Oxazoline Derivatives Using Burgess Reagent
Typical Procedure:
A solution of dipeptide 1 (56.4 mg, 0.16 mmol) in dry THF (3 mL) is added in a Pyrex tube and flushed with nitrogen. To this solution, Burgess reagent (41.9 mg, 0.176 mmol) is added in small portions and then, the mixture is heated at 70 °C for 0.7-2.5 h until the reaction is completed. After cooling to room temperature, the mixture is evaporated onto silica gel. The resultant residue is purified by column chromatography to give the desired oxazoline derivative 2 (39.6 mg, 74% yield).
A solution of dipeptide 1 (56.4 mg, 0.16 mmol) in dry THF (3 mL) is added in a Pyrex tube and flushed with nitrogen. To this solution, Burgess reagent (41.9 mg, 0.176 mmol) is added in small portions and then, the mixture is heated at 70 °C for 0.7-2.5 h until the reaction is completed. After cooling to room temperature, the mixture is evaporated onto silica gel. The resultant residue is purified by column chromatography to give the desired oxazoline derivative 2 (39.6 mg, 74% yield).
References
Application
Burgess Dehydration Reaction
Typical Procedure:
Burgess reagent (1.3 g, 5.5 mmol) is added to a solution of alcohol 1 (.6 g, 1.8 mmol) in anhydrous THF (4 mL) under N2 atmosphere, and the resulting solution is refluxed for 1 h. The mixture is poured into H2O, then extracted with AcOEt. The organic layer is washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified by SiO2 column chromatography (hexane : AcOEt = 1 : 1) to give the dehydrated product 2 in quantitive yield.
Refereces
- Enantioselective Total Synthesis of a Potent Antitumor Antibiotic, Fredericamycin A.
PubMed Literature
Documents
Product Articles
[TCIMAIL No.160] Organic Syntheses Utilizing the Chemical Properties of Chlorosulfonyl Isocyanate[TCIMAIL No.097] Burgess Reagent
Product Documents (Note: Some products will not have analytical charts available.)
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