1113-72-0

Usage

Abbreviation

AABN

Functional Groups

Nitrile group ( -CN )
Amine group ( -NH2 )
Ene group ( -CH=CH2 )

Application

Photoinitiator: Used in free radical polymerization reactions
Production: Commonly employed in plastic and resin material manufacturing
Synthesis: Utilized in the production of pharmaceutical compounds and organic chemistry research

Mechanism

Initiation: Under UV light, AABN undergoes fragmentation to initiate radical reactions
Result: Formation of polymer chains

Safety Precautions

Toxicity: AABN is toxic
Irritants: Can cause irritation to the skin, eyes, and respiratory system

Handling

Caution should be exercised when handling AABN

Upstream product

• 3141-59-1 2-acetyl-3-oxo-butyronitrile 
• 1118-61-2 3-Aminocrotononitrile 
• 75-36-5 acetyl chloride 
• 870-64-4 2-aminocrotononitrile 
• 2314-97-8 iodotrifluoromethane 
• 123-54-6 acetylacetone 
• 1113-71-9 2-Amino-3-cyano-penten-⁽²⁾-imin-⁽⁴⁾ 

Downstream Products

• 13950-66-8 3,5-dimethyl-4-isothiazolylcarbonitrile 
• 23198-55-2 3,5-dimethyl-1-phenylpyrazole-4-carbonitrile 

Relevant academic research and scientific papers

Vibrational assignment and structure of 4-amino-3-cyano-3-penten-2-one

Fourier transform infrared and Fourier transform Raman spectra of 4-amino-3-cyano-3-penten-2-one and its deuterated analogue have been obtained. Density functional theory (DFT) B3LYP and G96LYP calculations have been carried out with the purpose of understanding the vibrational spectra of this compound and its deuterated analogue. Vibrational wavenumbers calculated by B3LYP/6-31G* (with a p shell added on the amine protons) force field are closed with the experimental results. The percentage of deviation of the bond lengths and bond angles gives a good picture of the normal modes, and serves as a basis for the assignment of the wavenumbers. The calculated geometrical parameters show a strong intramolecular hydrogen bond with a N···O distance of 2.605-2.622 A?. This bond length is about 0.04-0.06 A? shorter than that in its parent, 4-amino-3- penten-2-one (with no cyano substitution in the α-position). Experimental evidences also indicate presence of an intermolecular hydrogen bond in the solid state, completely, and in solution, partially.

A short and expeditious regiospecific synthesis of novel pyrazoles

α-Cyano-β-enaminones, obtained by regioselective acylation of β-aminocrotononitrile, are smoothly and regiospecifically converted into substituted pyrazoles in good to excellent yields.

Studies on β-enaminonitriles: Part IV - Reaction of β-enaminonitriles with acid chlorides

Acylation of β-aminocrotononitrile with saturated acid chlorides in the presence of pyridine produces highly contrasting results. Thus, acylation with saturated straight-chain aliphatic acid chlorides shows exclusive preference for C-acylation whereas branched - chain acid chlorides shows a complete reversal of site selection giving only the corresponding N-acylated products. However, with aromatic acid chlorides no such clear-cut preference for regioselection has been observed. The position as well as the nature of the substituents are found to be critical in determining the site of acylation. With heteroaromatic acid chlorides the regioselection is found to be dependent on the nature of the heteroatom present in the ring.

RADICAL-ION PERFLUOROALKYLATION. VIII. REACTION OF PERFLUOROALKYL IODIDES WITH β-DIKETONES IN LIQUID AMMONIA

During the UV irradiation of perfluoroalkyl iodides with acetyl-, pivaloyl-, and benzoyl-acetone in liquid ammonia C-perfluoroalkylation of the β-diketones occurs with subsequent ammonolysis of the CF2 group at the α position to the carbanionic center.The acetyl group is removed, and β-perfluoroalkyl-β-aminovinyl ketones are formed.Trifluoroacetylacetone reacts similarly, but the CF3CO group is removed.The cyano derivative of the β-aminovinyl ketone, on which the acetyl group is preserved, was isolated from the products from the reaction of acetylacetone with trifluoroiodomethane.