4693-47-4

Usage

Uses

Used in Polymer Production:
4,4'-Azobis(4-cyano-1-pentanol) is used as a free radical initiator for the polymerization of various monomers, including acrylics, polyurethanes, and styrene-based polymers. Its ability to generate carbon-centered radicals upon decomposition facilitates the formation of polymer chains, resulting in the production of a wide range of polymers with diverse properties and applications.
Used in Nanomaterial Synthesis:
AIBN is utilized as a free radical initiator in the synthesis of nanomaterials, where its decomposition generates radicals that promote the growth and assembly of nanoparticles. This application allows for the controlled synthesis of nanomaterials with specific sizes, shapes, and properties, which can be further utilized in various fields such as electronics, medicine, and energy storage.
Used as a Crosslinking Agent in Hydrogel Manufacturing:
4,4'-Azobis(4-cyano-1-pentanol) is employed as a crosslinking agent in the production of hydrogels and other materials. Its ability to generate radicals upon decomposition promotes the formation of covalent bonds between polymer chains, resulting in the creation of a three-dimensional network structure. This crosslinking enhances the mechanical properties and stability of the hydrogels, making them suitable for various applications, including drug delivery, tissue engineering, and environmental remediation.
Safety Precautions:
Due to the potential hazards associated with 4,4'-Azobis(4-cyano-1-pentanol), it is crucial to handle and store the compound with care. Appropriate safety measures should be followed during its use, including the use of personal protective equipment, proper ventilation, and adherence to material safety data sheets. Additionally, AIBN should be stored in a cool, dry place, away from heat, light, and sources of ignition to prevent accidental decomposition and potential hazards.

Synthetic route

5-Hydroxy-2-pentanone (1071-73-4) + sodium cyanide (143-33-9) → 4,4′-azobis(4-cyano-1-pentanol) (4693-47-4)

Conditions	Yield
With hydrogenchloride; bromine; hydrazinium sulfate 1.) water, 20 deg C, 72 h, 2.) 4 h, 0 deg C; Yield given. Multistep reaction;

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + t-Butyldioxycarbonylbutyrylchlorid (50538-05-1) → 4-tert-Butylperoxycarbonyl-butyric acid 4-[4-(4-tert-butylperoxycarbonyl-butyryloxy)-1-cyano-1-methyl-butylazo]-4-cyano-4-methyl-butyl ester

Conditions	Yield
With pyridine at -0.1 - 9.9℃;	98%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + 3-(t-Butylperoxycarbonyl)-propionyl chloride (28839-26-1) → 3-tert-Butylperoxycarbonyl-propionic acid 4-[4-(3-tert-butylperoxycarbonyl-propionyloxy)-1-cyano-1-methyl-butylazo]-4-cyano-4-methyl-butyl ester

Conditions	Yield
With pyridine at -0.1 - 9.9℃;	96.6%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid 4-cyano-4-(1-cyano-4-methanesulfonyloxy-1-methyl-butylazo)-4-methyl-butyl ester

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	95%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + epichlorohydrin (106-89-8) → 4,4'-azobis(4-cyano-1-pentanolglycidyl ether)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 30℃; for 4h;	85%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + 2-dodecylsulfanylthiocarbonylsulfanyl-2-methyl-propionic acid (461642-78-4) → diazene-1,2-diylbis (4-cyanopentane-4,1-diyl) bis(2-(((dodecylthio)carbonothioyl)thio)-2-methylpropanoate)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	51%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) + bis(dodecylsulfanyl thiocarbonyl)disulfide (870532-86-8) → S-dodecyl-S'-[methylhydroxypropylcyanomethyl]trithiocarbonate (1394136-26-5)

Conditions	Yield
In ethyl acetate for 24h; Reflux;	48%

bis(thiobenzoyl) disulfide (5873-93-8) + 4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) → 4-cyano-1-hydroxypent-4-yl dithiobenzoate (211818-45-0)

Conditions	Yield
In ethyl acetate at 70℃; for 24h;	46%
In ethyl acetate at 70℃; for 24h;	46%

4,4′-azobis(4-cyano-1-pentanol) (4693-47-4) → 2-{1-Cyano-1-methyl-4-[2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethoxy]-butylazo}-2-methyl-5-[2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethoxy]-pentanenitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / NEt3 / CH2Cl2 / 2 h / 20 °C 2: 64 percent / KH / dimethylsulfoxide; tetrahydrofuran / 1.67 h / 20 °C View Scheme

Upstream product

• 1071-73-4 5-Hydroxy-2-pentanone 
• 143-33-9 sodium cyanide 

Downstream Products

• 211818-45-0 4-cyano-1-hydroxypent-4-yl dithiobenzoate 

Relevant academic research and scientific papers

Bifunctional initiators for free radical polymerization of non-crosslinked block copolymers

Novel bifunctional initiators have been designed with functional groups that independently produce free radicals. Initiators were synthesized to contain both diazene (-N=N-) and 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) moieties tethered by ester or ether linkages. It is anticipated that these compounds will be useful for producing a diverse number of block copolymers for applications in polymer-supported organic synthesis and materials science.