319-89-1

Basic information

• Product Name: Tetrahydroxyquinone
• Synonyms: Tetrahydroxy-P-BenzoquinoneGr;TETRAHYDROXY-P-QUINONE MONOHYDRATE 99%(TITR.);2,3,5,6-Tetrahydroxy-1,4-benzoquinone;Tetrahydroxy-p-quinone monohydrate,99%;Four hydroxy quinone;TETROQUINONE;TETRAHYDROXYQUINONE;TETRAHYDROXY-P-BENZOQUINONE
• CAS NO: 319-89-1
• Molecular Formula: C₆H₄O₆
• Molecular Weight: 172.09
• EINECS: 206-275-5
• Product Categories: Anthraquinones, Hydroquinones and Quinones;ANTHELCIDE
• Mol File: 319-89-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 280°
• Boiling Point: 262.37°C (rough estimate)
• Flash Point: 192.1 °C
• Appearance: blue-black crystals
• Density: 1.6695 (rough estimate)
• Vapor Pressure: 5.3E-07mmHg at 25°C
• Refractive Index: 1.7540 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.52±0.50(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• CAS DataBase Reference: Tetrahydroxyquinone(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydroxyquinone(319-89-1)
• EPA Substance Registry System: Tetrahydroxyquinone(319-89-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 319-89-1(Hazardous Substances Data)

Usage

Chemical Properties

blue-black crystals

Uses

anthelmintic

InChI:InChI=1/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H

Synthetic route

N,N'-dimethyltetrahydroxy-1,4-benzoquinonimine → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With hydrogenchloride; water Hydrolysis;	91%

rhodizonic acid (118-76-3) → tetrahydroxy-1,4-quinone (319-89-1) + 1-Benzyl-3-carbamoyl-pyridinium; hydroxide (19920-56-0)

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide In water; acetonitrile Ambient temperature;	A 70% B n/a

methyl 2-oxo-2-phenylacetate (15206-55-0) → tetrahydroxy-1,4-quinone (319-89-1) + (RS)-methyl mandelate (4358-87-6)

Conditions	Yield
With benzenehexol In water; acetonitrile Product distribution; Mechanism; Ambient temperature; other reagents: tetrahydroxy-p-benzoquinone or rhodizonic acid;	A 37% B 40%

benzenehexol (608-80-0) → tetrahydroxy-1,4-quinone (319-89-1) + (RS)-methyl mandelate (4358-87-6)

Conditions	Yield
With methyl 2-oxo-2-phenylacetate In water; acetonitrile Ambient temperature;	A 37% B 40%

Glyoxal (131543-46-9) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With water; sodium hydrogencarbonate; sodium sulfite beim Leiten von Luft,zuletzt bei 80-90grad;
With magnesium hydroxide; water; sodium hydrogensulfite at 50℃; Reagens 4:Kaliumcyanid ;und Erhitzen des Reaktionsgemisches auf Siedetemperatur;

inositol (551-72-4, 643-12-9, 6917-35-7, 39907-99-8, 40461-73-2, 41546-32-1, 41546-33-2, 41546-34-3, 41546-35-4, 41546-36-5) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With nitric acid man dampft die Reaktionsloesung bis zur Trockne ein und erhitzt darauf erst mit Alkohol, dann mit Wasser;

D-myo-inositol (87-89-8) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With nitric acid

benzenehexol (608-80-0) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With air; sodium carbonate man zersetzt das entstandenen Natriumsalz durch Kochen mit verd.Salzsaeure;
With air; water
With air; ethanol

sodium rhodizonate dibasic (523-21-7) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
In water Mechanism; Irradiation; pH = 10.9;

rhodizonic acid (118-76-3) → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With hydrogenchloride
Multi-step reaction with 2 steps 1: 1) 1-benzyl-1,4-dihydronicotinamide, 2) aq. HCl / 1) MeCN-H2O, room temp. 2: 37 percent / methyl benzoylformate / acetonitrile; H2O / Ambient temperature View Scheme

disodium-<1,2-dihydroxy-ethane-disulfonate-(1,2)> → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With potassium cyanide; magnesium hydroxide; water at 50℃; und Erhitzen des Reaktionsgemisches auf Siedetemperatur;

sodium disulfite compound of glyoxal → tetrahydroxy-1,4-quinone (319-89-1)

Conditions	Yield
With air; sodium carbonate at 50℃; das Dinatriumsalz entsteht;
With water; magnesium oxide das Dinatriumsalz entsteht;

tetrahydroxy-1,4-quinone (319-89-1) → diphenyl telluride (1202-36-4) + hexaketocyclohexane (527-31-1) + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With N-(p-tolylsulfonyl)diphenyltellurimide In methanol for 0.5h; Ambient temperature;	A 97% B 88% C 99%

tetrahydroxy-1,4-quinone (319-89-1) + (2-methoxyethoxy)methyltributylphosphonium hydroxide → C6O6(4-)*4C16H36O2P(1+)

Conditions	Yield
In methanol at 20℃; for 4.5h;	99%

tetrahydroxy-1,4-quinone (319-89-1) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → C6O6(4-)*4C16H36N(1+)

Conditions	Yield
In methanol at 20℃; for 4.5h;	99%

tetrahydroxy-1,4-quinone (319-89-1) → rhodizonic acid (118-76-3) + bis(4-methoxyphenyl)telluride (4456-34-2) + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide In methanol for 0.25h; Ambient temperature;	A 89% B 98% C 98%

N-methoxymethyl-N-methylpyrrolidinium hydroxide + tetrahydroxy-1,4-quinone (319-89-1) → 4C7H16NO(1+)*C6O6(4-)

Conditions	Yield
In methanol at 20℃; for 4.5h;	90%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-methylmercaptobenzimidazol-1-ylmethyl)benzene → C36H24N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	85%

tetrahydroxy-1,4-quinone (319-89-1) + N-(2-methoxyethoxy)methyl-N-methylpyrrolidinium hydroxide → 4C9H20NO2(1+)*C6O6(4-)

Conditions	Yield
In methanol at 20℃; for 4.5h;	84%

tetrahydroxy-1,4-quinone (319-89-1) → tetralithium salt of tetrahydroxybenzoquinone

Conditions	Yield
With lithium methanolate In methanol for 134h; Inert atmosphere;	80%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-(2-furan-yl)benzimidazol-1-ylmethyl)-2,5-dimethoxybenzene → [(CO)3Re(μ-THBQ)(μ-(1,4-bis(2-(2-furan-yl)benzimidazol-1-ylmethyl)-2,5-dimethoxybenzene))Re(CO)3]

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; High pressure;	80%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,3,5-tri(2-(thiophene-2-yl)benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene (1449138-83-3) + toluene (108-88-3) → [Re2(CO)6(1,3,5-tri(2-(thiophene-2-yl)benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene)(tetrahydroxy-1,4-quinone)]*toluene

Conditions	Yield
at 160℃; for 48h; Autoclave;	75%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-(2-thiophen-yl)benzimidazol-1-ylmethyl)-2,5-dimethoxybenzene → [(CO)3Re(μ-THBQ)(μ-(1,4-bis(2-(2-thiophen-yl)benzimidazol-1-ylmethyl)-2,5-dimethoxybenzene))Re(CO)3]

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; High pressure;	75%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,3,5-tris(2-methylmercaptobenzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene (1422504-74-2) + toluene (108-88-3) → [Re2(CO)6(1,3,5-tri(2-(methylthio)benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene)(tetrahydroxy-1,4-quinone)]*toluene

Conditions	Yield
at 160℃; for 48h; Autoclave;	74%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis((2-(thiophen-2-yl)benzimidazol-1-yl)methyl)benzene → [(CO)3Re(μ-THBQ)(μ-(1,4-bis(2-(2-thiophen-yl)benzimidazol-1-ylmethyl)benzene))Re(CO)3]

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; High pressure;	72%

tetrahydroxy-1,4-quinone (319-89-1) + 1,3-bis((2-(thiophen-2-yl)benzimidazol-1-yl)methyl)benzene + dirhenium decacarbonyl → C42H24N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; Autoclave;	72%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-(2-furan-yl)benzimidazol-1-ylmethyl)benzene → [(CO)3Re(μ-THBQ)(μ-(1,4-bis(2-(2-furan-yl)benzimidazol-1-ylmethyl)benzene))Re(CO)3]

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; High pressure;	70%

tetrahydroxy-1,4-quinone (319-89-1) + 1,3-bis-(2-(2-thiophen-yl)benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene + dirhenium decacarbonyl → C45H30N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; Autoclave;	70%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-methylmercaptobenzimidazol-1-ylmethyl)-2,5-dimethylbenzene → C38H28N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	68%

tetrahydroxy-1,4-quinone (319-89-1) + 1-Benzyl-1,4-dihydronicotinamide (952-92-1) → 2,3,4,5,6-Pentahydroxy-phenolate1-benzyl-3-carbamoyl-pyridinium; (104286-48-8)

Conditions	Yield
In water; acetonitrile Ambient temperature;	65%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,3-bis(2-methylmercaptobenzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene → C39H30N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	65%

tetrahydroxy-1,4-quinone (319-89-1) + 1,3-bis(2-([2,2'-bithiophen]-5-yl)benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene + dirhenium decacarbonyl → C53H34N4O12Re2S4

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h; Autoclave;	65%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,3-bis(2-(methylmercapto)benzimidazol-1-ylmethyl)benzene → C36H24N4O12Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	64%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) + 1,4-bis(2-methylmercaptobenzimidazol-1-ylmethyl)-2,5-dimethoxybenzene → C38H28N4O14Re2S2

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	62%

ferrous(II) sulfate heptahydrate + tetrahydroxy-1,4-quinone (319-89-1) → 6C6O6(4-)*12Fe(2+)*6H2O

Conditions	Yield
In water; diethylene glycol at 120℃; for 48h; Inert atmosphere;	61%

tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) → C22O22Re4 (1568080-72-7)

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 48h;	60.2%

tetrahydroxy-1,4-quinone (319-89-1) + cobalt(II) diacetate tetrahydrate (6147-53-1) → 6C6O6(4-)*8H2O*12Co(2+)

Conditions	Yield
In water at 120℃; for 48h; Autoclave;	60%

p-phenylpyridine (939-23-1) + tetrahydroxy-1,4-quinone (319-89-1) + decacarbonyldirhenium(0) (14285-68-8) → [{Re(CO)3}6(benzenehexaolate)(4-phenylpyridine)6]n

Conditions	Yield
In 1,3,5-trimethyl-benzene at 160℃; for 72h; Autoclave;	57.8%

tetrahydroxy-1,4-quinone (319-89-1) + hexaaquairon(II) tetrafluoroborate + tris[(2-pyridylmethyl)amine] (16858-01-8) → [diiron(II)(tris(2-pyridylmethyl)amine)2(μ-2,3,5,6,-tetrahydroxy-1,4-benzoquinoate)](BF4)2

Conditions	Yield
With NEt3 In methanol MeOH soln. of Fe complex added to MeOH soln. of C18H18N4 and C6(OH)4O2 in a wet box (<1 ppm O2); neutralized (NEt3), refluxed for 1 h; filtered while hot, filtrate kept at room temp. for 2-3 d; filtered off,washed (MeOH), dried in vacuo; elem. anal.;	55%

tetrahydroxy-1,4-quinone (319-89-1) + manganese (II) acetate tetrahydrate (6156-78-1) → 6C6O6(4-)*8H2O*12Mn(2+)

Conditions	Yield
In water at 120℃; for 48h; Autoclave;	53%

Upstream product

• 319-88-0 1,3,5-Trichloro-2,4,6-trifluorobenzene 
• 319-87-9 1-Fluoropentachlorobenzene 
• 319-86-8 delta-1,2,3,4,5,6-Hexachlorocyclohexane 
• 3198-65-0 1-AMINO-2-METHYLCYCLOPENTANECARBOXYLIC ACID 
• 319-85-7 beta-1,2,3,4,5,6-Hexachlorocyclohexane 
• 31984-90-4 (1S,4aα,γS)-Decahydro-5β-hydroxymethyl-γ,5,8aβ-trimethyl-2-methylene-1-naphthalene-1-pentanol 
• 3198-49-0 Ethyl D-glucopyranoside 
• 3198-47-8 2-Amino-4-(methylthio)-butyronitrile 
• 31984-70-0 sodium 4-sulfanylbenzenesulfonate 
• 31984-61-9 DUGUETINE 
• 319-84-6 ALPHA-HCH 
• 31984-55-1 3-chloro-1-[({4-[(oxoammonio)methylidene]pyridin-1(4H)-yl}methoxy)methyl]pyridinium dichloride 
• 31984-14-2 p-Toluenesulfonamide, N-(4-chloro-3-oxobutyl)- 
• 3198-41-2 11-DEHYDROTETRAHYDROCORTICOSTERONE 

Downstream Products

• 3199-05-1 1-phenyl-4-pyrazolecarboxamide 
• 319905-65-2 1H-Pyrrole-3,4-dicarboxylicacid,2-(3-pyridinyl)-,dimethylester(9CI) 
• 319906-45-1 7-Bromo-2-iodo-9,9-dimethyl-9H-fluorene 
• 319906-50-8 4,6-DIMETHOXY-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID 
• 319906-52-0 1-ethyl-4,6-dimethoxy-1H-indole-2-carboxylic acid 
• 319906-53-1 Carbamic acid, [(3S,4R)-4-methyl-3-pyrrolidinyl]-, 1,1-dimethylethyl ester (9CI) 
• 31990-82-6 5-(1H-IMIDAZOL-2-YL)-QUINOLINE 
• 31991-03-4 1-tert-butyl-3-{[(2,6-dimethylphenyl)carbamoyl]oxy}pyrrolidinium chloride 
• 319910-53-7 (DIMETHYLVINYLSILYLOXY)HEPTACYCLOPENT& 
• 31991-19-2 S-76 
• 3199-12-0 2-(trichloromethyl)benzamide 
• 319912-39-5 3H-Pyrrolizine-5-carboxaldehyde, 3-oxo- (9CI) 
• 31991-29-4 2-[(3-Trifluoromethylphenyl)amino]-N-(4-nitrophenyl)-3-pyridinecarboxamide 
• 319913-91-2 2-Propanone,1-(3-ethoxy-4-hydroxyphenyl)-,oxime(9CI) 

Recommend Products

• 131543-46-9  Glyoxal 
• 4358-87-6  (RS)-methyl mandelate 
• 608-80-0  benzenehexol 
• 2528-61-2  Heptanoic acid chloride 
• 3642-68-0  tetrahydroxy-p-benzoquinone tetraoctanoate 
• 111-64-8  n-octanoic acid chloride 
• 6147-53-1  cobalt(II) diacetate tetrahydrate 
• 6156-78-1  manganese (II) acetate tetrahydrate 
• 7664-93-9  sulfuric acid 
• 7647-01-0  hydrogenchloride 
• 10034-85-2  hydrogen iodide 
• 7783-06-4  hydrogen sulfide 
• 142-61-0  Hexanoyl chloride 
• 118-76-3  rhodizonic acid