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CAS RN: 141556-45-8 | Product Number: D3446
1,3-Dimesitylimidazolium Chloride
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Purity: >98.0%(HPLC)
Synonyms:
- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium Chloride
- IMes·HCl
Product Documents:
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| Product Number | D3446 |
Purity / Analysis Method 
|
>98.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__2__1H__2__5ClN__2 = 340.90 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Room Temperature (Recommended in a cool and dark place, <15°C) |
| Packaging and Container
|
1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 141556-45-8 |
| Reaxys Registry Number | 5468834 |
| PubChem Substance ID | 87559077 |
| MDL Number | MFCD02684541 |
Specifications
| Appearance | White to Light yellow powder to crystal |
| Purity(HPLC) | min. 98.0 area% |
| Purity(with Total Nitrogen) | min. 96.0 % |
Properties (reference)
| Melting Point | 352 °C |
| Solubility (soluble in) | Methanol |
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. 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. |
Related Laws:
Transport Information:
| H.S.code* | 2933.29-000 |
Application
Ester-amide Exchange Reactions of Vinyl Esters Using N-Heterocyclic Carbene (NHC) Catalysts
Experimental procedure:
A suspension of potassium tert-butoxide (2.8 mg, 0.025 mmol) and IMes·HCl (10.2 mg, 0.03 mmol) in anhydrous toluene (1.0 mL) is stirred at ambient temperature for 0.5 h. A vinyl ester (0.5 mmol) and an amine (0.75 mmol) are added subsequently and the solution is stirred at 60 °C. The crude mixture is purified by flash silica gel column chromatography to give the desired product.
A suspension of potassium tert-butoxide (2.8 mg, 0.025 mmol) and IMes·HCl (10.2 mg, 0.03 mmol) in anhydrous toluene (1.0 mL) is stirred at ambient temperature for 0.5 h. A vinyl ester (0.5 mmol) and an amine (0.75 mmol) are added subsequently and the solution is stirred at 60 °C. The crude mixture is purified by flash silica gel column chromatography to give the desired product.
References
- N-Heterocyclic carbene-catalysed amidation of vinyl esters with aromatic amines
Application
NHC-catalyzed Difluorocarbene Generation and Aryl Difluoromethyl Ether Synthesis
Typical Procedure (Entry 2):
To a toluene solution (0.4 mL) of 1,3-dimesitylimidazolium chloride (IMes·HCl) (2.7 mg, 0.0079 mmol), sodium carbonate (8.5 mg, 0.080 mmol), and 6,7-dimethyl-α-tetralone (70 mg, 0.40 mmol) is added trimethylsilyl difluoro(fluorosulfonyl)acetate (100 µL, 0.48 mmol) at room temperature. The reaction mixture is stirred and heated at 80 °C for 1 h. After cooling the resulting mixture to room temperature, DDQ (182 mg, 0.80 mmol) and toluene (2 mL) are added and the mixture is heated at 100 °C for 2 h. Purification by column chromatography (SiO2, hexane) gives the desired product (82 mg, Y. 91%) as a colorless liquid.
To a toluene solution (0.4 mL) of 1,3-dimesitylimidazolium chloride (IMes·HCl) (2.7 mg, 0.0079 mmol), sodium carbonate (8.5 mg, 0.080 mmol), and 6,7-dimethyl-α-tetralone (70 mg, 0.40 mmol) is added trimethylsilyl difluoro(fluorosulfonyl)acetate (100 µL, 0.48 mmol) at room temperature. The reaction mixture is stirred and heated at 80 °C for 1 h. After cooling the resulting mixture to room temperature, DDQ (182 mg, 0.80 mmol) and toluene (2 mL) are added and the mixture is heated at 100 °C for 2 h. Purification by column chromatography (SiO2, hexane) gives the desired product (82 mg, Y. 91%) as a colorless liquid.
References
- N-Heterocyclic carbene-catalyzed difluorocarbene generation and its application to aryl difluoromethyl ether synthesis
Application
Regioselectivity-Switchable Hydroarylation of Styrenes
Reference
PubMed Literature
Documents
Product Articles
[Research Articles] Ester-amide Exchange Reactions of Vinyl Esters Using N-Heterocyclic Carbene (NHC) Catalysts[Research Articles] Regioselectivity-Switchable Hydroarylation of Styrenes
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