2370-18-5

Basic information

• Product Name: GALVINOXYL
• Synonyms: 1-ylidene)-;2,6-di-tert-butyl-alpha-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-p-tolylox;coppinger’sradical;Coppinger'S radical;galvanoxyl;galvinoxylradical;galvinoxyradical;Phenol, 2,6-di(tert-butyl)-4-(3,5-di(tert-butyl)-4-oxo-2,5-cyclohexadien-1-ylidenemethyl)-,radical ion(1-)
• CAS NO: 2370-18-5
• Molecular Formula: C₂₉H₄₁O₂
• Molecular Weight: 421.63
• EINECS: 219-133-2
• Mol File: 2370-18-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 158-159 °C(lit.)
• Boiling Point: 478.49°C (rough estimate)
• Flash Point: 216.9°C
• Appearance: Dark blue to purple/Crystalline Powder, Crystals and/or Chunks
• Density: 1.0321 (rough estimate)
• Refractive Index: 1.5045 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Hexane (Slightly)
• Merck: 14,4357
• CAS DataBase Reference: GALVINOXYL(CAS DataBase Reference)
• NIST Chemistry Reference: GALVINOXYL(2370-18-5)
• EPA Substance Registry System: GALVINOXYL(2370-18-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: XV7978000
• Hazardous Substances Data: 2370-18-5(Hazardous Substances Data)

Usage

Description

Galvinoxyl is a dark blue fine crystalline powder that serves as a free radical and free-radical scavenger. It is known for its ability to store electrical energy in organic radical batteries as an electromotive material.

Uses

Used in Organic Radical Batteries:
Galvinoxyl is used as an electromotive material for storing electrical energy in organic radical batteries. Its free radical properties contribute to the efficient functioning and energy storage capacity of these batteries.
Used as a Free Radical Scavenger:
Galvinoxyl is utilized as a free-radical scavenger, playing a crucial role in neutralizing free radicals that can cause damage to cells and contribute to various diseases and aging processes. Its ability to scavenge free radicals makes it a valuable compound in the field of health and medicine.

Purification Methods

It is a stable free radical scavenger of short-lived free radicals with odd electrons on C or O. It is best prepared freshly by oxidation

InChI:InChI=1/C29H41O2/c1-26(2,3)20-14-18(15-21(24(20)30)27(4,5)6)13-19-16-22(28(7,8)9)25(31)23(17-19)29(10,11)12/h13-17H,1-12H3

Synthetic route

1-Chloro-4-iodobenzene (637-87-6) + 2,6-di-tert-butyl-α-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl (2370-18-5) + 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide (50978-45-5) + phenylboronic acid (98-80-6) → C35H45ClO2

Conditions	Yield
With potassium phosphate; sodium carbonate; N-ethyl-N,N-diisopropylamine at 120℃; for 24h; Mechanism;	58%

2,6-di-tert-butyl-α-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl (2370-18-5) → 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Conditions	Yield
With N-phenylsalicylaldimine In ethyl acetate at 25℃; Kinetics; Reagent/catalyst; Solvent;

2,6-di-tert-butyl-α-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl (2370-18-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C35H53BO4

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; acetonitrile at 20℃; for 3h; Inert atmosphere; Schlenk technique; Glovebox; Electrochemical reaction;

Upstream product

• 128-39-2 2,6-di-tert-butylphenol 
• 4359-97-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone 
• 2700-36-9 Tetra-tert-butylindophenoxyl 
• 118-82-1 4,4'-Methylenebis(2,6-di-tert-butylphenol) 
• 50-00-0 formaldehyd 

Downstream Products

• 103330-88-7 bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methoxy-methane 
• 4359-97-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone 
• 597-63-7 tetraethylgermane 
• 993-62-4 hexaethyldigermane 
• 13937-05-8 octaethyltrigermane 
• 3265-03-0 trimesitylgermane 
• 62120-68-7 chlorotri(2,4,6-trimethylphenyl)germane 
• 153789-61-8 (HO((CH₃)3C)2C₆H₂)2CHGe(C₆H₅)2Cl 
• 118-82-1 4,4'-Methylenebis(2,6-di-tert-butylphenol) 
• 1613-66-7 dichlorodiphenylgermane 
• 153789-58-3 (HO((CH₃)3C)2C₆H₂)2CHGe(C₆H₅)Cl₂ 
• 1074-29-9 trichlorophenylgermane 
• 153789-59-4 (HO((CH₃)3C)2C₆H₂)CH₂C₆H₂(C(CH₃)3)2OGe(C₆H₅)Cl₂ 
• 1019663-55-8 [((t)Bu₂PCH₂SiMe₂)2N]Co(galvinoxyl) 

Relevant articles and documents

Bond Dissociation Enthalpy of α-Tocopherol and Other Phenolic Antioxidants

The equilibrium constants, K1, for the reaction between galvinoxyl and a series of phenolic antioxidants have been determined by means of EPR spectroscopy.With aroxyl radicals decaying at appreciable rates, K1 was obtained by performing kinetic analyses of the time dependence of the concentrations of the equilibrating radicals after mixing the reactants.In two cases the temperature dependence of K1 was also studied and the entropy change for the equilibration reaction was determined.Bond dissociation enthalpies, DH, of the ArO-H bond of the examined phenols were calculated by comparison with the known value of 2,4,6-tri-tert-butylphenol (81.24 kcal mol-1).A larger than expected DH value was found for probucol (81.03 kcal mol-1) and an explanation of this behavior was given in terms of the preferred conformation adopted by the para alkylthio group.The DH value of α-tocopherol (78.93 kcal mol-1) was found to be very close to that of the phenolic precursor of galvinoxyl (78.80 kcal mol-1) and somewhat larger than that of 2,6-di-tert-butyl-4-methoxyphenyl (77.61 kcal mol-1).