615-94-1

Basic information

• Product Name: 2,5-DIHYDROXY-1,4-BENZOQUINONE
• Synonyms: 4-dione,2,5-dihydroxy-5-cyclohexadiene-1;p-Benzoquinone, 2,5-dihydroxy-;2,5-Dihydroxybenzoquinone,98%;2,5-Dihydroxy-2,5-cyclohexadiene-1,4-dione;3,6-Dihydroxy-2,5-cyclohexadiene-1,4-dione;Dihydroxy-p-quinonate acid;2,5-Dihydroxy-1,4-benzoquinone,98%;2,5-Dihydroxy-1,4-benzoquinone, 98% 25GR
• CAS NO: 615-94-1
• Molecular Formula: C₆H₄O₄
• Molecular Weight: 140.09
• EINECS: 210-454-3
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Benzoquinones;Alcohols;Monomers;Polymer Science
• Mol File: 615-94-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 235 °C (dec.)(lit.)
• Boiling Point: 216.56°C (rough estimate)
• Flash Point: 162.9 °C
• Appearance: Ochre to brown/Powder
• Density: 1.4596 (rough estimate)
• Vapor Pressure: 2.24E-05mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: pK1:2.71;pK2:5.18 (25°C)
• Water Solubility: Soluble in water.
• BRN: 1939229
• CAS DataBase Reference: 2,5-DIHYDROXY-1,4-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIHYDROXY-1,4-BENZOQUINONE(615-94-1)
• EPA Substance Registry System: 2,5-DIHYDROXY-1,4-BENZOQUINONE(615-94-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 615-94-1(Hazardous Substances Data)

Usage

Chemical Properties

Ochre to brown powder

Uses

2,5-dihydroxy-1,4-benzoquinone dianion, and squarate as bridging ligands in the synthesis and magnetic properties of binuclear iron(III) complexes with oxalate. A Dinuclear 2,5-Dihydroxy-1,4-benzoquinone acts as a bridging ligand Ruthenium(II) Complex with the Dianion.

Synthesis Reference(s)

Journal of the American Chemical Society, 67, p. 1034, 1945 DOI: 10.1021/ja01222a504

InChI:InChI=1/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H

Synthetic route

recorcinol (108-46-3) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With peracetic acid; acetic acid	80%
With peracetic acid

hydroquinone (123-31-9) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide at 40 - 50℃; for 1.5h;	79%
With sodium hydroxide; dihydrogen peroxide at 50℃;
With sodium hydroxide; dihydrogen peroxide
With water; dihydrogen peroxide; sodium hydroxide at 45 - 55℃; for 3.5h; Inert atmosphere;
With 2(A-F),3(A-F),6(B-F)-heptadecakis-O-methyl-6(A)-deoxy-6(A)-oxo-α-cyclodextrin; dihydrogen peroxide at 25℃; for 1h; pH=7; Kinetics; Reagent/catalyst; aq. phosphate buffer;

2-hydroxy-phenoxazin-3-one (1915-49-7) + furan-2,3,5(4H)-trione pyridine (1:1) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 2-amino-phenol (95-55-6)

2,5-dimethoxyquinone (3117-03-1) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide
Multi-step reaction with 2 steps 1: ethanol 2: aq. NaOH solution View Scheme

2,5-bis(phenylamino)-1,4-benzoquinone (3421-08-7) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide

2,5-bis(methylamino)-1,4-benzoquinone (1654-14-4) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sodium hydroxide

2-amino-5-hydroxy-[1,4]benzoquinone-4-imine (119014-47-0) + furan-2,3,5(4H)-trione pyridine (1:1) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
at 70℃;

2-amino-5-anilino-[1,4]benzoquinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 5-anilino-2-hydroxy-1,4-benzoquinone (124251-44-1)

Conditions	Yield
With sodium hydroxide

benzene-1,2-diol (120-80-9) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide; oxygen
With sodium hydroxide; dihydrogen peroxide

Dimethyl oxalate (553-90-2) + 3,3-dimethoxy-butan-2-one (21983-72-2) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
(i) NaOMe, (ii) H2SO4, (iii) Mg(OMe)2; Multistep reaction;

2,5-bis(1-aziridinyl)-1,4-benzoquinone (526-62-5) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 2,5-bis((2-hydroxyethylyl)amino)-1,4-benzoquinone (5557-53-9) + 2-ethylenimino-5-hydroxy-1,4-benzoquinone + 2-ethanolamino-5-hydroxy-1,4-benzoquinone + 2-ethanolamino-5-ethylenimino-1,4-benzoquinone

Conditions	Yield
In N,N-dimethyl acetamide; water at 40℃; for 24h; Rate constant; Kinetics; Thermodynamic data; product yield/distribution; mechanism; apparent activation energy; 0.01 M phosphate buffer (pH 8); examination of pH (further buffers), ionic strength, buffer concentration and reaction time;

4,5-dimethoxy-1,2-benzoquinone (21086-65-7) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide In methanol

1,4-Benzochinon-2,5-di-(3-oxypropansaeure) (72391-34-5) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sodium hydroxide at 70℃;

hydroquinone (123-31-9) → p-benzosemiquinone radical anion (3225-29-4, 106-51-4) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + p-benzoquinone (106-51-4)

Conditions	Yield
With sodium hydroxide; potassium dihydrogenphosphate; air; Ag(1-x)H(x)Zr2(PO4)3 In water for 1h; Mechanism; Product distribution; Ambient temperature; Irradiation; pH 6, irradiation absence, other reaction time, various reactants ratio;
With sodium hydroxide; potassium dihydrogenphosphate; air; Ag(1-x)H(x)Zr2(PO4)3 In water Ambient temperature; Irradiation; Yields of byproduct given;

hydroquinone (123-31-9) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + p-benzoquinone (106-51-4)

Conditions	Yield
With sodium hydroxide; potassium dihydrogenphosphate; air; Ag(1-x)H(x)Zr2(PO4)3 In water for 4.16667h; Irradiation; Yield given. Yields of byproduct given;

2-aminophenoxazin-3-one (1916-59-2) + furan-2,3,5(4H)-trione pyridine (1:1) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + ammonia (7664-41-7) + 2-amino-phenol (95-55-6)

dihydrogen peroxide (7722-84-1) + 4-methyl-1,2-dihydroxybenzene (452-86-8) + aqueous KOH → carbon dioxide (124-38-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + oxalic acid (144-62-7)

2.5-bis-dimethylamino-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide Ansauern die erhaltene Loesung;

2.5-dianilino-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With ethanol; sulfuric acid

2.5-diethoxy-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide

2-amino-5-anilino-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sodium hydroxide
With sulfuric acid

2-oxy-5-amino-benzoquinone-(1.4)-imide-(1) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide at 70℃;
With sodium hydroxide at 70℃;

2-oxy-5-amino-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sulfuric acid

2-oxy-5-anilino-quinone-monoanil → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With potassium hydroxide

2-oxy-5-anilino-quinone → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sulfuric acid
With sodium hydroxide

4.5-bis-methylamino-benzoquinone-(1.2) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With sodium hydroxide

2,5-bis(phenylamino)-1,4-benzoquinone (3421-08-7) + alcoholic KOH-solution → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

basic sodium salt of/the/ 3.6-dioxy-benzoquinone-(1.4)-dicarboxylic acid-(2.5) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

Conditions	Yield
With mineral acid

N-methyl-phenoxazine-quinone-(2.3) → 2,5-dihydroxy-1,4-benzoquinone (615-94-1)

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydroxyphenazine (19220-18-9)

Conditions	Yield
In water at 100℃;	100%
In water at 80℃; for 18h;	100%
In ethanol for 1.5 - 24h; Product distribution / selectivity; Heating / reflux;	93%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 3,4-diaminobenzoic acid (619-05-6) → 7,8-dihydroxyphenazine-2-carboxylic acid (1055878-48-2)

Conditions	Yield
In water at 95℃; for 15h;	100%
In ethanol for 24h; Reflux;	85%
With acetic acid In ethanol at 20℃; for 5h;	65%

4,5-Dichloro-1,2-phenylenediamine (5348-42-5) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2,3,9,10-tetrachloro-5,14-dihydroquinoxalino[2,3-b]phenazine

Conditions	Yield
In neat (no solvent) at 160℃; Inert atmosphere; Schlenk technique;	100%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4,5-dibromo-1,2-diaminobenzene (49764-63-8) → 2,3,9,10-tetrabromo-5,14-dihydroquinoxalino[2,3-b]phenazine

Conditions	Yield
With acetic acid at 100℃; Inert atmosphere; Schlenk technique;	100%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + tetrabutylammomium bromide (1643-19-2) + nickel(II) acetate tetrahydrate (6018-89-9) → 1.5C6H2O4(2-)*Ni(2+)*C16H36N(1+)

Conditions	Yield
In water at 100℃; for 0.75h; Inert atmosphere;	100%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 1,2,4,5-benzenetetrol (636-32-8)

Conditions	Yield
With hydrogenchloride; tin at 95℃; for 1h;	99%
With hydrogenchloride; tin In water for 1h; Reflux;	98%
With hydrogenchloride; tin	78%

1H-benzimidazol-2-amine (934-32-7) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2-amino-1H-benzo[d]imidazol-3-ium 3-hydroxy-1-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-2,5,6-trioxocyclohex-3-en-1-ide (1367748-62-6)

Conditions	Yield
In chloroform for 4h; Reflux;	99%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + orthaminic acid (7474-78-4) → 7,8-dihydroxy-phenazine-2-sulfonic acid

Conditions	Yield
In water Reflux;	99%
In water for 16h; Reflux;	86%
In water at 95℃; for 18h;	84%

(5-methyl-pyridin-2-yl)amine (1603-41-4) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2C6H8N2*C14H8N4O12

Conditions	Yield
In chloroform for 4h; Reflux;	97%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-nitrobenzaldehdye (555-16-8) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) → trans-2-(4-chlorobenzoyl)-5-hydroxy-3-(4-nitrophenyl)-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	97%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) → disodium salt of 2,5-dihydroxy-1,4-benzoquinone (41104-64-7, 108724-19-2)

Conditions	Yield
With sodium methylate In dimethyl sulfoxide for 48h;	96.6%
With sodium methylate In methanol at 20℃;

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + silver nitrate → C6H2(O)2(OAg)2 (146110-13-6)

Conditions	Yield
With triethylamine In ethanol; triethylamine; acetonitrile byproducts: NEt3*HNO3; a soln. of quinone in Et3N and EtOH were added dropwise under N2 to a soln. of AgNO3 in MeCN-EtOH in the dark at 25°C, the mixt. was stirred for 2 h; filtd., ppt. was washed with cold EtOH, filtrate evapd. under vac.; elem. anal.;	96%

manganese sulfate pentahydrate + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) + water (7732-18-5) → Mn(2,5-dihydroxy-1,4-benzoquinone(-2H))(H2O)2

Conditions	Yield
In water MnSO4*5H2O and quinone deriv. mixed in water; ppt. washed with water and EtOH; elem. anal.;	96%
In water slow diffusion of aq. solns. of MnSO4*5H2O and quinone deriv. at room temp. for several d;

2-aminopyridine (504-29-0) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2C5H6N2*C14H8N4O12

Conditions	Yield
In chloroform for 4h; Reflux;	96%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-nitrobenzaldehdye (555-16-8) + dimedone (126-81-8) → 3,3,10,10-tetramethyl-7,14-bis(4-nitrophenyl)-3,4,10,11-tetrahydrochromeno[2,3-b]xanthene-1,6,8,13(2H,7H,9H,14H)-tetraone

Conditions	Yield
With poly(2-ethyl-2-oxazoline) immobilized on silica-coated Fe3O4 nanoparticles In ethanol for 5h; Reflux; Green chemistry;	96%
With L-proline In water for 4h; Reflux; Green chemistry;	70%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) + 2-nitro-benzaldehyde (552-89-6) → trans-2-(4-chlorobenzoyl)-5-hydroxy-3-(2-nitrophenyl)-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	96%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + Diphenylphosphinic chloride (1499-21-4) → C18H14ClO5P

Conditions	Yield
With aluminum (III) chloride In toluene at 25℃; for 24h;	96%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-methoxyphenylene-1,2-diamine dihydrochloride (59548-39-9) → 2,3-dihydroxy-6-methoxyphenazine (13161-92-7)

Conditions	Yield
With triethylamine In ethanol Heating;	95%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 1,2-diamino-benzene (95-54-5) → 5,14-dihydro-5,7,12,14-tetraazapentacene (111076-33-6)

Conditions	Yield
at 180℃;	95%
at 160℃; for 5h; Inert atmosphere; Neat (no solvent);	94.8%
In benzyl alcohol at 135 - 140℃; for 20h;	92%
With acetic acid for 8h; Reflux; Inert atmosphere;

2-Amino-6-methylpyridine (1824-81-3) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2C6H8N2*C14H8N4O12

Conditions	Yield
In chloroform for 4h; Reflux;	94%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-fluorobenzaldehyde (459-57-4) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) → trans-2-(4-chlorobenzoyl)-3-(4-fluorophenyl)-5-hydroxy-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	94%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 2-Fluorobenzaldehyde (446-52-6) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) → trans-2-(4-chlorobenzoyl)-3-(2-fluorophenyl)-5-hydroxy-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	94%

2-amino-4-(trifluoromethyl)phenol hydrochloride (112250-01-8) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → C20H8F6N2O2 (1038848-16-6)

Conditions	Yield
With acetic acid Reflux;	93.6%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + benzaldehyde (100-52-7) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) → trans-2-(4-chlorobenzoyl)-5-hydroxy-3-phenyl-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	93%

3-methylpyridin-2-ylamine (1603-40-3) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2,5-dihydroxy-1,4-benzoquinone (615-94-1) → 2C6H8N2*C14H8N4O12

Conditions	Yield
In chloroform for 4h; Reflux;	92%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 3-nitro-benzaldehyde (99-61-6) + dimedone (126-81-8) → 3,3,10,10-tetramethyl-7,14-bis(3-nitrophenyl)-3,4,10,11-tetrahydrochromeno[2,3-b]xanthene-1,6,8,13(2H,7H,9H,14H)-tetraone

Conditions	Yield
With poly(2-ethyl-2-oxazoline) immobilized on silica-coated Fe3O4 nanoparticles In ethanol for 5h; Reflux; Green chemistry;	92%
With L-proline In water for 4h; Reflux; Green chemistry;	70%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) + 4-cyanobenzaldehyde (105-07-7) → trans-2-((4-chlorobenzoyl)-5-hydroxy-4,7-dioxo-2,3,4,7-tetrahydrobenzofuran-3-yl)benzonitrile

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	92%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-bromo-benzaldehyde (1122-91-4) + 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2) → trans-3-(4-bromophenyl)-2-(4-chlorobenzoyl)-5-hydroxy-2,3-dihydrobenzofuran-4,7-dione

Conditions	Yield
With cholin hydroxide In water for 5h; Reflux; Green chemistry;	92%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-methoxy-benzaldehyde (123-11-5) + dimedone (126-81-8) → 7,14-bis(4-methoxyphenyl)-3,3,10,10-tetramethyl-3,4,10,11-tetrahydrochromeno[2,3-b]xanthene-1,6,8,13(2H,7H,9H,14H)-tetraone

Conditions	Yield
With poly(2-ethyl-2-oxazoline) immobilized on silica-coated Fe3O4 nanoparticles In ethanol for 4h; Reflux; Green chemistry;	92%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 4-methyl-1,2-diaminobenzene (496-72-0) → 3,10-dimethyl-5,12-dihydro-quinoxalino[2,3-b]phenazine

Conditions	Yield
With acetic acid In ethanol for 24h; Heating;	91%

Upstream product

• 1915-49-7 2-hydroxy-phenoxazin-3-one 
• 120-80-9 benzene-1,2-diol 
• 123-31-9 hydroquinone 
• 108-46-3 recorcinol 
• 553-90-2 Dimethyl oxalate 
• 21983-72-2 3,3-dimethoxy-butan-2-one 
• 1916-59-2 2-aminophenoxazin-3-one 
• 7722-84-1 dihydrogen peroxide 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 7664-93-9 sulfuric acid 
• 124251-44-1 5-anilino-2-hydroxy-1,4-benzoquinone 
• 119014-47-0 2-amino-5-hydroxy-[1,4]benzoquinone-4-imine 
• 143810-02-0 tetraethyl (3,6-dichloro-1,4-benzoquinone-2,5-diyl)dimalonate 
• 120-72-9 indole 

Downstream Products

• 20765-04-2 2,5-diethoxy-[1,4]benzoquinone 
• 2164-97-8 2,8-dihydroxy-10-(4-hydroxy-phenyl)-10H-phenoxazine-1,4,6,9-tetraone 
• 107770-91-2 1,2,4,5-Benzenetetrol Tetraacetate 
• 107792-76-7 3-(4-Pyridyl)-1,2,4,5-benzenetetrol Tetraacetate 
• 90785-78-7 1,4-bis<2-(4-hydroxyphenyl)ethylamino>cyclohexa-2,5-diene-1,2,4,5-tetrol 
• 107825-18-3 2,5-Dihydroxy-1,4-benzoquinone, Acridine Complex 
• 107792-78-9 3-(9-Acridyl)-1,2,4,5-benzenetetrol Tetraacetate 
• 107792-80-3 2,5-Dihydroxy-1,4-benzoquinone, 3-Picoline Complex 
• 107792-77-8 3-<4-(3-Methylpyridyl)>-1,2,4,5-benzenetetrol Tetraacetate 
• 90785-79-8 1,4-bis<2-(imidazol-4-yl)ethylamino>cyclohexa-2,5-diene-1,2,4,5-tetrol 
• 124251-41-8 5-hydroxy-N-(2'-phenylethyl)-2-(2-phenylethylamino)-1,4-benzoquinone imine 
• 90785-77-6 1,4-bis(phenylethylamino)cyclohexa-2,5-diene-1,2,4,5-tetrol 
• 31914-12-2 2,5-Dihydroxybenzochinonsulfoniumylid 
• 28293-40-5 2,5-Dioxo-3,6-bis-(dimethylsulfonium)-1,4-benzochinon-bis-betain 

Relevant articles and documents

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A turn-on fluorescent chemosensor selectively detects cyanide in pure water and food sample

A turn-on fluorescent chemosensor (H-1) for cyanide anions based on dihydroxy phenazine was designed and synthesised. The sensor H-1 exhibits high sensitivity and good selectivity for cyanide in pure water. The CN- response mechanism involves a hydrogen bonding and deprotonation process in the sensor, which induced prominent fluorescence enhancement. The detection limit of the sensor toward CN- is 5.65 × 10-7 M, and other anions had nearly no influence on the probing behavior. In addition, test strips based on the sensor were fabricated, which also exhibit a good selectivity to CN- in water. Notably, this sensor was successfully applied to detect CN- in food samples, which proves a very simple and selective platform for on-site monitoring of CN- in agriculture samples.

A Strategic High Yield Synthesis of 2,5-Dihydroxy-1,4-benzoquinone Based MOFs

Metal organic frameworks (MOFs) of the type NBu4M(DHBQ)1.5 (M = Ni2+, Fe2+, and Co2+ DHBQ = 2,5-dihydroxy-1,4-benzoquinone) were prepared with improved yield up to 100% via a simple benchtop aqueous addition reaction. For the first time, the crystalline phase of this formula polymer was synthesized without in situ generation of the DHBQ ligand from 2, 5-diamino-1,4-benzoquinone (DABQ). Powder X-ray diffraction and elemental analysis confirm the crystalline phase and composition of products. Infrared and electron dispersive spectroscopy further confirm that the materials are homologous to the reported single crystalline polymers. The present MOF synthesis can be extended to halide-substituted ligands, i.e., 3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone (chloranilic acid, CAN) and 3,6-difluoro-2,5-dihydroxy-1,4-benzoquinone (fluoranilic acid, FAN).

Degradation of the Cellulosic Key Chromophore 5,8-Dihydroxy-[1,4]-naphthoquinone by Hydrogen Peroxide under Alkaline Conditions

5,8-Dihydroxy-[1,4]-naphthoquinone (DHNQ) is one of the key chromophores in cellulosic materials. Its almost ubiquitous presence in cellulosic materials makes it a target molecule of the pulp and paper industry's bleaching efforts. In the presented study, DHNQ was treated with hydrogen peroxide under alkaline conditions at pH 10, resembling the conditions of industrial hydrogen peroxide bleaching (P stage). The reaction mechanism, reaction intermediates, and final degradation products were analyzed by UV/vis, NMR, GC-MS, and EPR. The degradation reaction yielded C1-C4 carboxylic acids as the final products. Highly relevant for pulp bleaching are the findings on intermediates of the reaction, as two of them, 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ) and 1,4,5,8-naphthalenetetrone, are potent chromophores themselves. While DHBQ is one of the three key cellulosic chromophores and its degradation by H2O2 is well-established, the second intermediate, 1,4,5,8-naphthalenetetrone, is reported for the first time in the context of cellulose discoloration.