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

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

• 131543-46-9 Glyoxal 
• 551-72-4 inositol 
• 87-89-8 D-myo-inositol 
• 608-80-0 benzenehexol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 118-76-3 rhodizonic acid 
• 523-21-7 sodium rhodizonate dibasic 

Downstream Products

• 3117-06-4 tetramethoxy-p-benzoquinone 
• 488-64-2 2r,3c,4c,5c,6c-pentahydroxy-cyclohexanone 
• 20129-59-3 2,5-diacetoxy-3,6-dihydroxy-[1,4]benzoquinone 
• 20129-61-7 tetraacetoxy-[1,4]benzoquinone 
• 608-80-0 benzenehexol 
• 5096-13-9 1-benzylnicotinamide chloride 
• 1202-36-4 diphenyl telluride 
• 527-31-1 hexaketocyclohexane 
• 70-55-3 toluene-4-sulfonamide 
• 118-76-3 rhodizonic acid 
• 4456-34-2 bis(4-methoxyphenyl)telluride 
• 104286-48-8 2,3,4,5,6-Pentahydroxy-phenolate1-benzyl-3-carbamoyl-pyridinium; 
• 3642-68-0 tetrahydroxy-p-benzoquinone tetraoctanoate 
• 576-63-6 cis-inositol 

Relevant articles and documents

Transformations of myo-inositol hexa-0-nitrate under the action of amines

Reactions of myo-inositiol hexa-0-nitrate with ammonia and primary amines yield tetrahydroxy-1,4-benzoquinone derivatives, viz., its tetraammonium salt and its diimines, respectively. Reactions with secondary and tertiary amines give salts of rhodizonic acid, which are converted into salts of croconic acid under certain conditions. The reactions with secondary amines involve intermediate formation of radical species, which were dectected by ESR spectroscopy. A scheme for the chemical transformations of myo-inositol hexa-0-nitrate under the action of amines was proposed.

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.

The photochemistry of the rhodizonate dianion in aqueous solution

The photochemistry of the rhodizonate dianion at 483 nm has been studied in aqueous solution at pH 8.3.In the absence of oxygen no reaction was observed.In the presence of oxygen, 6.2 x 10-5 M, the dianion was consumed with a quantum yield of 0.044.The oxidation apparently did not involve the formation of O2(1Δg).Electron transfer from the excited dianion was observed with methyl viologen.

REDUCTION OF METHYL BENZOYLFORMATE BY REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE MODEL IN THE PRESENCE OF RHODIZONIC ACID

The reduction of rhodizonic acid (RA) with 1-benzyl-1,4-dihydronicotinamide (BNAH; NADH model) was carried out at room temperature to obtain tetrahydroxy-p-quinone (THQ) and hexahydroxybenzene (HHB) by two-electron and four-electron reductions, respectively.The reduction of methyl benzoylformate with BNAH proceded smoothly in the presence of RA, although it could not be reduced at all without RA.