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CAS RN: 14338-32-0 | Product Number: C0903

2-Chloro-1-methylpyridinium Iodide


Purity: >98.0%(T)
Synonyms:
Documents:
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
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 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.
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Transport Information:
Application
TCI Practical Example: Peptide coupling reagent: Mukaiyama condensation reagent

Used Chemicals

Procedure

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.

Experimenter's Comments

Consumption of stating material and formation of product was monitored by LCMS.

Analytical Data(Boc-Pro-Phe-OMe)

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).

Lead Reference


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


PubMed Literature


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