4693-47-4

Basic information

• Product Name: 4,4'-Azobis(4-cyano-1-pentanol)
• Synonyms: 2-(2-cyano-5-hydroxy-pentan-2-yl)diazenyl-5-hydroxy-2-methyl-pentanenitrile;4,4'-Azobis(4-cyano-1-pentanol);4,4'-AZO-BIS-(4-CYANO PENTANOL);AZOPENTANOL C;AZOPENTANON-C;4,4'-AZOBIS[4-CYANO PENTANOL] 98+%;2-(2-diethylaminoethylamino)-5-nitroaniline;4,4'-AZO-BIS[4-CYANOL PENTANOL]
• CAS NO: 4693-47-4
• Molecular Formula: C₁₂H₂₀N₄O₂
• Molecular Weight: 252.31
• EINECS: 1592732-453-0
• Product Categories: Industrial/Fine Chemicals;Active Pharmaceutical Ingredients
• Mol File: 4693-47-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 417.4 °C at 760 mmHg
• Flash Point: 206.2 °C
• Appearance: /
• Density: 1.08 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: 4,4'-Azobis(4-cyano-1-pentanol)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Azobis(4-cyano-1-pentanol)(4693-47-4)
• EPA Substance Registry System: 4,4'-Azobis(4-cyano-1-pentanol)(4693-47-4)

Safety Data

• Hazardous Substances Data: 4693-47-4(Hazardous Substances Data)

Usage

General Description

4,4'-Azobis(4-cyano-1-pentanol) is a chemical compound commonly used as a free radical initiator in polymerization reactions. It has the molecular formula C14H20N4O2 and is often referred to as AIBN. 4,4'-Azobis(4-cyano-1-pentanol) decomposes when heated or exposed to light, releasing nitrogen gas and forming carbon-centered radicals, which initiate the polymerization process. AIBN is widely used in the production of various polymers, including acrylics, polyurethanes, and styrene-based polymers. It is also used in the synthesis of nanomaterials and as a crosslinking agent in the manufacture of hydrogels and other materials. Due to its potential hazards, AIBN should be handled and stored with care, and its use should be in accordance with appropriate safety measures.

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 articles and documents

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.