2-Chloro-1,3-dimethylimidazolinium Chloride is coupling reagent used for very difficult couplings. Very strong acylating agents due to the chloride active specie, which is one of the best leaving groups. However, they can provoke racemization, if the carboxylic group of Fmoc-amino acids has a chiral center. Ideally can be used for coupling or fragment condensation where you have hindered amino acids which are not prone to racemization.
CAS: 37091-73-9
Synonym: 2-Chloro-1,3-dimethylimidazolinium chloride
Properties
Purity
≥98.0%
Molecular Formula
C5H10Cl2N2
Molecular Weight
169.05 [gr/mol]
Appearance
Off-white to light yellow or yellow solid
Storage Conditions
Store in cool place.
Store under inert gas. Moisture sensitive.
Applications
- 2-Chloro-1,3-dimethylimidazolinium Chloride is coupling reagent used for very difficult couplings.
- Very strong acylating agents due to the chloride active specie, which is one of the best leaving groups.
- Can provoke racemization, if the carboxylic group of Fmoc-amino acids has a chiral center.
- Can be used for coupling or fragment condensation where you have hindered amino acids which are not prone to racemization.
Studies
-
2-Chloro-1,3-dimethylimidazolinium Chloride. 1. A Powerful Dehydrating Equivalent to DCC
Toshio Isobe and Tsutomu IshikawaThe Journal of Organic Chemistry 1999 64 (19), 6984-6988DOI: 10.1021/jo990210y
-
2-Chloro-1,3-dimethylimidazolinium Chloride. 2. Its Application to the Construction of Heterocycles through Dehydration Reactions
Toshio Isobe and Tsutomu IshikawaThe Journal of Organic Chemistry 1999 64 (19), 6989-6992DOI: 10.1021/jo9909756
-
2-Chloro-1,3-dimethylimidazolinium Chloride. 3. Utility for Chlorination, Oxidation, Reduction, and Rearrangement Reactions
Toshio Isobe and Tsutomu IshikawaThe Journal of Organic Chemistry 1999 64 (16), 5832-5835DOI: 10.1021/jo990211q