1-butyl-3-vinylimidazolium chloride

• CAS: 657394-65-5
• Catalog Number: ACM657394655-1
• Category: Main Products
• Molecular Weight: 186.68
• Molecular Formula: C9H15N2Cl
• Synonyms: 1-Vinyl-3-ButylImidazolium Chloride
• Appearance: Liquid
• Chemical Formula: VBIMCl

Case Study

1-Butyl-3-vinylimidazolium Chloride as a Precursor for Advanced Initiator Systems in Polyisobutylene Production

Yousefi, Saleh, et al. Journal of Molecular Liquids 367 (2022): 120381.

In this work, 1-butyl-3-vinylimidazolium chloride (the vinyl monomer form of a common imidazolium ionic liquid) was used as a building block to produce (a) a polymeric ionic liquid (PIL) by radical polymerization and (b) halloysite-supported ionic liquid functionality (S-IL). And explored how those materials were incorporated into an AlCl3 / ionic-liquid initiator family for the cationic polymerization of isobutylene to conventional-grade polyisobutylene (PIB) under mild conditions.
Synthesis of PIL: The 1-butyl-3-vinylimidazolium chloride monomer was polymerized by conventional radical initiation (AIBN, 0.03 g per 1 g monomer) in toluene at 80 °C for 4 h to yield the PIL, which was isolated by methanol washing and vacuum drying.
Representative polymerization process: Polymerizations were carried out in a 1 L stainless-steel reactor. The reactor was purged with argon at 100 °C for 30 min and then cooled to the target temperature. The initiator composition typically contained AlCl3 and the IL or PIL at a 2:1 molar ratio, whereas for the S-IL system an AlCl3:S-IL molar ratio was 1:24 (mol/mol). Ethanol was included at an ethanol:AlCl3 molar ratio of 1:2. Approximately 300 g of isobutylene monomer was charged and the reaction run for 1 h. After reaction, the product was discharged, washed repeatedly with 5 wt% NaOH solution, and purified by rotary evaporation at 150 °C under ~0.8 bar vacuum to remove water, unreacted monomer and low-molecular-weight oligomers.

1-Butyl-3-Vinylimidazolium Chloride: A Polymerizable Ionic-Liquid Monomer for Electro-Responsive Chitosan Semi-IPN Biomaterials

Kanaan, Akel F., et al. Materials Science and Engineering: C 121 (2021): 111798.

1-butyl-3-vinylimidazolium chloride (BVImCl) was employed as a functional monomer used to produce ionic-liquid-based polymers and copolymers that are incorporated into chitosan semi-interpenetrating networks (semi-IPNs). BVImCl-derived polycations (poly(BVImCl) and poly(HEMA-co-BVImCl)) enabled formation of mechanically robust, positively charged hydrogels that are electro-responsive and show accelerated electrically driven delivery of a model charged drug (lidocaine hydrochloride), low haemolysis and strong haemostatic activity - properties relevant to wound-dressing and iontophoretic patch applications.
Hydrogel Synthesis: Semi-IPN hydrogels were prepared by first dissolving chitosan in acetic acid to form a homogeneous solution. BVImCl monomer was then incorporated along with crosslinker MBA. After degassing and nitrogen purging, polymerization was initiated using AIBA at 70°C for 8 hours. Three distinct hydrogel formulations were developed: s-IPN/PIL (containing poly(BVImCl)), s-IPN/COP (incorporating poly(HEMA-co-BVImCl)), and control materials without BVImCl for comparative analysis.
Performance: The s-IPN/PIL and s-IPN/COP hydrogels exhibited high mechanical stability and maintained positive surface charge across a broad pH range. Under external electrical stimulus, the BVImCl-containing hydrogels showed significantly enhanced drug permeation and release capabilities. The kinetic release constants increased by approximately 1.5-fold, while diffusion coefficients were more than 2.7 times higher compared to passive release conditions. All BVImCl-derived materials demonstrated non-haemolytic characteristics (haemolytic index ≤0.2%) and exhibited strong haemostatic activity with blood clotting indices of approximately 12±1%.

Custom Q&A

What is the molecular formula of 1-butyl-3-vinylimidazolium chloride?

The molecular formula of 1-butyl-3-vinylimidazolium chloride is C9H15ClN2.

What is the molecular weight of 1-butyl-3-vinylimidazolium chloride?

The molecular weight of 1-butyl-3-vinylimidazolium chloride is 186.68 g/mol.

What is the IUPAC name of 1-butyl-3-vinylimidazolium chloride?

The IUPAC name of 1-butyl-3-vinylimidazolium chloride is 1-butyl-3-ethenylimidazol-1-ium chloride.

What is the InChI of 1-butyl-3-vinylimidazolium chloride?

The InChI of 1-butyl-3-vinylimidazolium chloride is InChI=1S/C9H15N2.ClH/c1-3-5-6-11-8-7-10(4-2)9-11;/h4,7-9H,2-3,5-6H2,1H3;1H/q+1;/p-1.

What is the InChIKey of 1-butyl-3-vinylimidazolium chloride?

The InChIKey of 1-butyl-3-vinylimidazolium chloride is KRCYUCRTMSTHOK-UHFFFAOYSA-M.

What is the canonical SMILES of 1-butyl-3-vinylimidazolium chloride?

The canonical SMILES of 1-butyl-3-vinylimidazolium chloride is CCCC[N+]1=CN(C=C1)C=C.[Cl-].

How many hydrogen bond donor count does 1-butyl-3-vinylimidazolium chloride have?

1-butyl-3-vinylimidazolium chloride has 0 hydrogen bond donor count.

How many hydrogen bond acceptor count does 1-butyl-3-vinylimidazolium chloride have?

1-butyl-3-vinylimidazolium chloride has 1 hydrogen bond acceptor count.

How many rotatable bond count does 1-butyl-3-vinylimidazolium chloride have?

1-butyl-3-vinylimidazolium chloride has 4 rotatable bond count.

What is the topological polar surface area of 1-butyl-3-vinylimidazolium chloride?

The topological polar surface area of 1-butyl-3-vinylimidazolium chloride is 8.8 ?2.