2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride
[CAS# 27776-21-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Azo, diazonium compound
• Name: 2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride
• Synonyms: VA 044; Vazo 044; Vazo 44WSP; Wako VA 044
• Molecular Formula: C₁₂H₂₂N₆^.2(HCl)
• Molecular Weight: 323.27
• CAS Registry Number: 27776-21-2
• EC Number: 248-655-3
• SMILES: CC(C)(C1=NCCN1)N=NC(C)(C)C2=NCCN2.Cl.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P280-P301+P312-P302+P352-P304+P340-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H413
Acute toxicity	Acute Tox.	4	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Self-heating substances or mixtures	Self-heat.	2	H252
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Eye irritation	Eye Irrit.	2B	H320
Specific target organ toxicity - single exposure	STOT SE	3	H370
Skin irritation	Skin Irrit.	2	H315
Skin mild irritation	Skin Mild Irrit. 99	3	H316
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride, commonly known as AIBI, is an organic compound with the molecular formula C10H18Cl2N4. It is a water-soluble, organic azo compound that contains imidazoline and azo functional groups. AIBI is primarily used as a radical initiator in polymerization reactions, where it plays a significant role in the production of polymers, particularly in the field of controlled polymerization processes.

The discovery of 2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride emerged from research on azobisisobutyronitrile (AIBN), a well-known radical initiator, and its derivatives. AIBI was synthesized with the aim of developing an azo compound that would exhibit improved solubility and more controlled reactivity in aqueous systems compared to traditional radical initiators like AIBN. The imidazoline group incorporated in AIBI contributes to its stability and solubility, enhancing its performance in aqueous-based polymerization systems.

AIBI is widely used in the synthesis of polymers, particularly in controlled polymerization techniques. It serves as an initiator in processes like free-radical polymerization and copolymerization of vinyl monomers. Its ability to generate free radicals upon decomposition makes it effective for initiating the polymerization of a variety of monomers, including acrylic and styrene-based monomers. This property has made AIBI valuable in industries such as coatings, adhesives, and plastic production.

In addition to its use in polymer chemistry, 2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride is employed in the preparation of functionalized materials. The compound is used to produce materials with specific properties, such as hydrophilic or hydrophobic characteristics, by controlling the polymerization conditions and incorporating specific functional groups into the polymer backbone. AIBI-based polymerization also allows for the creation of nanomaterials and microgels that have applications in drug delivery, sensors, and environmental remediation.

AIBI’s use in polymer chemistry extends to research on controlled or "living" polymerization techniques. The compound is utilized in systems where precise control over the molecular weight, distribution, and architecture of the polymer is desired. Such control is crucial for producing high-performance materials that meet specific industrial requirements, including the development of polymers with improved mechanical, thermal, and chemical properties.

In summary, 2,2'-Azobis[2-(imidazolin-2-yl)propane] dihydrochloride is an important compound in polymer science, particularly as a radical initiator in controlled polymerization reactions. Its solubility in water, stability, and effectiveness in initiating polymerization processes make it a valuable tool in the production of high-performance materials with specific functional properties. Its applications span across various industries, including coatings, adhesives, and drug delivery systems, where it plays a critical role in the development of advanced polymer-based materials.