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CAS RN: 14338-32-0 | Product Number: C0903
2-Chloro-1-methylpyridinium Iodide
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Purity: >98.0%(T)
Synonyms:
Product Documents:
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| 25G |
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| Product Number | C0903 |
| Purity / Analysis Method | >98.0%(T) |
| Molecular Formula / Molecular Weight | C__6H__7ClIN = 255.48 |
| 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 | Light Sensitive,Hygroscopic |
| CAS RN | 14338-32-0 |
| Reaxys Registry Number | 3572320 |
| PubChem Substance ID | 87565959 |
| SDBS (AIST Spectral DB) | 10163 |
| Merck Index (14) | 6301 |
| MDL Number | MFCD00011984 |
Specifications
| Appearance | Light yellow to Amber to Dark green powder to crystal |
| Purity(HPLC) | min. 95.0 area% |
| Purity(Nonaqueous Titration) | min. 98.0 % |
| Solubility in Water | almost transparency |
Properties (reference)
GHS
| Pictogram |
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| 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* | 2933.39-000 |
Application
TCI Practical Example: Peptide coupling reagent: Mukaiyama condensation reagent
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Used Chemicals
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Procedure
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Boc-Pro-OH (1.65 g, 7.65 mmol), 2-chloro-1-methylpyridinium iodide (1.95 g, 7.65 mmol) were added to solution of H-Phe-OMe･HCl (1.50 g，6.95 mmol) in dichloromethane (30 mL) at room temperature and triethylamine (3.40 mL, 24.3 mmol) was added dropwise in 3 min at 5 to 10 °C. After stirring for 3 h, solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with 10% citric acid aq. (30 mL × 3), 5% sodium bicarbonate solution aq. (30 mL × 3) and brine (30 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. After the removal of solvent under reduced pressure, the given crude was purified by column chromatography (hexane : EtOAc = 2 : 1) to give Boc-Pro-Phe-OMe (2.37 g，91%) as a slightly yellowish solid.
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Experimenter's Comments
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Consumption of stating material and formation of product was monitored by LCMS.
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Analytical Data（Boc-Pro-Phe-OMe）
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1H NMR (400 MHz, DMSO-d6); δ 8.17–8.27 (m, 1H), 7.19–7.29 (m, 5H), 4.42–4.53 (m, 1H), 4.00–4.13 (m, 1H), 3.56–3.61 (m, 3H), 3.18–3.38 (m, 2H), 2.90–3.08 (m, 2H), 1.91–2.11 (m, 1H), 1.56–1.71 (m, 3H), 1.15-1.40 (m, 9H).
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Lead Reference
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- A facile synthesis of carboxamides by using 1-methyl-2-halopyridinium iodides as coupling reagents
Application
A Mukaiyama Condentation Reagent
Experimental procedure3): To a solution of monoallyl malonate (5.22 g, 36.25 mmol) in dichloromethane (100 mL) is added 2-chloro-1-methylpyridinium iodide (13.90 g, 54.38 mmol), followed by N-methylaniline (4.31 mL, 39.88 mmol). The mixture is cooled to 0 °C and triethylamine (25.2 mL, 181.3 mmol) is added dropwise. The resulting mixture is stirred at 0 °C for 5 min, then allowed to warm to room temperature and stirred at this temperature for 30 min. The reaction mixture is diluted with aq. HCl (10%, 100 mL). The organic phase is separated, washed with aq. NaHCO3 (100 mL) and brine (100 mL), then dried (MgSO4) and concentrated in vacuo. Flash column chromatography [Petrol:EtOAc 2:1] affords 1 (7.78 g, 92%) as a pale yellow oil.
References
- 1) A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXYLIC ESTERS
- 2) A FACILE SYNTHESIS OF CARBOXAMIDES BY USING 1-METHYL-2-HALOPYRIDINIUM IODIDES AS COUPLING REAGENTS
- 3) Asymmetric Decarboxylative Allylation of Oxindoles
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