106-34-3

Basic information

• Product Name: Quinhydrone
• Synonyms: p-Benzoquinone-hydroquinone compound (1:1);2,5-Cyclohexadiene-1,4-dione, compd. with 1,4-benzenediol (1:1);p-Benzoquinone, compd. with hydroquinone (1:1);Green hydroquinone;benzene-1,4-diol; cyclohexa-2,5-diene-1,4-dione;Hydroquinone(HQ);2,5-Cyclohexadiene-1,4-dione compd. with 1,4-benzenediol (1:1);Hydroquinone, compd. with p-benzoquinone;p-Benzoquinhydrone;Chinhydron [Czech];p-Benzoquinone, compd. with hydroquinone;2,5-Cyclohexadiene-1,4-dione,compounds,compd. with 1,4-benzenediol (1:1);2, 5-Cyclohexadiene-1,4-dione, compd. with 1,4-benzenediol (1:1)
• CAS NO: 106-34-3
• Molecular Formula: C₆H₄O₂*C₆H₆O₂
• Molecular Weight: 218.2054
• EINECS: 203-387-6
• Product Categories: Hydroquinone;API intermediates;Benzoquinones
• Mol File: 106-34-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 168-172℃
• Boiling Point: 286 °C at 760 mmHg
• Flash Point: 141.6 °C
• Appearance: green crystalline powder
• Density: 1.40
• Vapor Pressure: 0.00157mmHg at 25°C
• Refractive Index: 1.4270 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 4g/l
• Water Solubility: 4 g/L (20℃)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,8058
• BRN: 3919222
• CAS DataBase Reference: Quinhydrone(CAS DataBase Reference)
• NIST Chemistry Reference: Quinhydrone(106-34-3)
• EPA Substance Registry System: Quinhydrone(106-34-3)

Safety Data

• Hazard Codes: Xn:Harmful;;
• Statements: R22:; R36/37/38:; R50:
• Safety Statements: S26:; S29:; S37/39:; S61:
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: VA4550000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 106-34-3(Hazardous Substances Data)

Usage

Chemical Properties

a dark green crystalline powder which is a complex formed by benzoquinone and hydroquinone. Quinhydrone is a general reagent used in potentiometric titrations. It can also be used as a π-acceptor in the formation of charge-transfer complex of analytes for spectrophotometric analysis.

Uses

Different sources of media describe the Uses of 106-34-3 differently. You can refer to the following data:
1. In pH determinations (quinhydrone electrode).
2. Quinhydrone is a hydrogen bonded 1:1 charge transfer complex of hydroquinone and p-benzo-quinone having semiconducting properties. Quinhydrone is addition compound of one mol hydroquinone and one mol Benzoquinone. Quinhydrone electrode is a type of redox electrode which can be used to measure the hydrogen ion concentration (pH) of a solution in a chemical experiment. Quinhydrone/methanol treatment for the measurement of carrier lifetime in crystalline silicon substrates has been reported. Surface passivation of silicon substrates by quinhydrone/ethanol treatment has been investigated.
3. Used to measure the hydrogen ion concentration (pH) of a solution in a chemical experiment. It provides an alternative to the commonly used glass electrode in a pH meter.

General Description

Quinhydrone/methanol treatment for the measurement of carrier lifetime in crystalline silicon substrates has been reported. Surface passivation of silicon substrates by quinhydrone/ethanol treatment has been investigated.

Hazard

Toxic by ingestion.

Purification Methods

Crystallise quinhydrone from H2O at 65o , then dry it in vacuo.[Beilstein 7 H 617, 7 IV 2069.]

InChI:InChI=1/C6H6O2.C6H4O2/c2*7-5-1-2-6(8)4-3-5/h1-4,7-8H;1-4H

Synthetic route

di-tert-butyliminoxyl (33802-06-1) + 4-hydroxycyclohexa-2,5-dien-1-one (4323-21-1) → quinhydrone (106-34-3)

Conditions	Yield
at -30℃;	99%

phenol (108-95-2) → quinhydrone (106-34-3)

Conditions	Yield
With hydroquinone; p-benzoquinone; copper(l) chloride In acetonitrile	94.1%
With mineral acid at 12 - 17℃; Oxydation;

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester (105398-69-4) + p-benzoquinone (106-51-4) → bicyclohexyl-3,6-diene-2,5-dione (3116-98-1) + quinhydrone (106-34-3) + 3-cyclohexyl-2-(pyridine-2-thiyl)-1,4-benzoquinone (117749-44-7)

Conditions	Yield
In dichloromethane at 0℃; for 0.5h; Irradiation;	A 7% B n/a C 83%

(3,3-diphenylpropanoyloxy)-2-pyridinethione (109276-74-6) + p-benzoquinone (106-51-4) → 1-(1,4-Benzochinonyl)-2,2-diphenylethan (34708-59-3) + quinhydrone (106-34-3) + 3-(2,2-diphenylethyl)-2-(pyridine-2-thiyl)-1,4-benzoquinone (117749-43-6)

Conditions	Yield
In dichloromethane at 0℃; for 0.5h; Irradiation;	A 7% B n/a C 80%

N-(3,3-diphenylpropionyloxy)-pyridine-2-thione (91534-05-3) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3) + 2-(1-Benzyl-2-phenyl-ethyl)-[1,4]benzoquinone (117749-41-4) + 3-(1,3-diphenylpropan-2-yl)-2-(pyridine-2-thiyl)-1,4-benzoquinone (117749-45-8)

Conditions	Yield
In dichloromethane at 0℃; for 0.5h; Irradiation;	A n/a B 10% C 78%

N-palmitoxy-2-pyridinethione (89025-67-2) + p-benzoquinone (106-51-4) → 2-n-Pentadecyl-1,4-benzoquinone (41427-22-9) + quinhydrone (106-34-3) + 3-(1-pentadecyl)-2-(pyridine-2-thiyl)-1,4-benzoquinone (117749-42-5)

Conditions	Yield
In dichloromethane at 0℃; for 0.5h; Irradiation;	A 10% B n/a C 77%

hydroquinone (123-31-9) → quinhydrone (106-34-3)

Conditions	Yield
With at 50℃; for 1h; Irradiation; solid state;	64%
With sodium sulfate Oxydation;
With sulfuric acid at 0℃; Oxydation; unter Verwendung von Wechselstrom;

phenol (108-95-2) → quinhydrone (106-34-3) + p-benzoquinone (106-51-4)

Conditions	Yield
With 5,10,15,20-tetrakis(4-sulfophenyl)porphine; oxygen In water for 5h; Mechanism; Time; Solvent; Irradiation;	A n/a B 8.9%

4-aminotriphenylamine (2350-01-8) → N,N'-diphenyl-1,4-phenylenediamine (6246-98-6, 73334-88-0, 73334-89-1) + quinhydrone (106-34-3)

Conditions	Yield
With ethanol

(+)-proto-quercitol (488-73-3) → quinhydrone (106-34-3) + hydroquinone (123-31-9) + p-benzoquinone (106-51-4)

Conditions	Yield
at 280 - 290℃; im Vakuum;

(3-oxo-1-phenyl-1,3-dihydro-isobenzofuran-1-yl)-[1,4]benzoquinone (60047-81-6) + hydroquinone (123-31-9) → quinhydrone (106-34-3)

bis-dibenzo[a,kl]xanthen-1-yl-peroxide (120579-49-9) + hydroquinone (123-31-9) → quinhydrone (106-34-3) + diphenyl hydrazine (122-66-7) + Azobenzene (1227476-15-4)

diethyl ether (60-29-7) + chloranil (118-75-2) + hydroquinone (123-31-9) + benzene (71-43-2) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + quinhydrone (106-34-3)

benzaldehyde (100-52-7) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3) + 2,5-dihydroxy-benzophenone; compound with [1,4]benzoquinone

Conditions	Yield
Aussetzen dem direkten Sonnenlicht im geschlossenen Rohr;

acetaldehyde (75-07-0) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
im Sonnenlicht;

peracetic acid (79-21-0) + acetic acid (64-19-7) + hydroquinone (123-31-9) → quinhydrone (106-34-3)

tetraethylphosphonium iodide (4317-06-0) + acetic acid (64-19-7) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3)

N-ethylquinolinium iodide (634-35-5) + acetic acid (64-19-7) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3)

4-anilinophenol (122-37-2) + p-benzoquinone (106-51-4) → 4-(phenylimino)cyclohexa-2,5-dienone (2406-04-4) + quinhydrone (106-34-3)

ethanol (64-17-5) + tetranitromethane (509-14-8) + hydroquinone (123-31-9) → quinhydrone (106-34-3) + N,N-dimethyl-aniline (121-69-7)

ethanol (64-17-5) + N,N'-diphenyl-1,4-phenylenediamine (6246-98-6, 73334-88-0, 73334-89-1) + hydroquinone (123-31-9) → N,N'-diphenyl-1,4-phenylenediamine (74-31-7) + quinhydrone (106-34-3)

hexanitroethane (918-37-6) + hydroquinone (123-31-9) → quinhydrone (106-34-3)

4-methylbenzo-1,2-quinone (3131-54-2) + hydroquinone (123-31-9) → quinhydrone (106-34-3) + p-benzoquinone (106-51-4)

Conditions	Yield
red form;

2,6-dichloro-1,4-benzoquinone (697-91-6) + hydroquinone (123-31-9) → quinhydrone (106-34-3) + 2,6-dichloro-[1,4]benzoquinone; compound of 2.6-dichloro-quinone with 2.6-dichloro-hydroquinone (60300-96-1)

Conditions	Yield
With diethyl ether; Petroleum ether

hydroquinone (123-31-9) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3)

Conditions	Yield
In solid for 1440h; Ambient temperature; microscopic investigation of the crystalline complex formation;
at 30℃; Thermodynamic data; other temperatures for solid state interaction; E(act.);

diethyl ether (60-29-7) + hydroquinone (123-31-9) + isopentyl nitrite (110-46-3) → quinhydrone (106-34-3) + p-benzoquinone (106-51-4)

hydroquinone (123-31-9) → quinhydrone (106-34-3) + p-benzoquinone (106-51-4)

Conditions	Yield
plaetzlich ueber seinen Sublimationspunkt erhitzen;
im ultravioletten Licht;
beim Erhitzen ueber den Sublimationspunkt;
With sulfuryl dichloride; diethyl ether

bianthronyl (434-84-4) + acetone (67-64-1) + p-benzoquinone (106-51-4) → bianthrone (434-85-5) + quinhydrone (106-34-3)

diethyl ether (60-29-7) + ethanethiol (75-08-1) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3)

ethanethiol (75-08-1) + p-benzoquinone (106-51-4) → quinhydrone (106-34-3)

dihydroxyfumaric acid (133-38-0) + quinhydrone (106-34-3) → DL-tartaric acid (133-37-9)

4-acetamidobenzenesulfinic acid (710-24-7) + quinhydrone (106-34-3) → N-(4-((2,5-dihydroxyphenyl)sulfonyl)phenyl)acetamide (100867-36-5)

Conditions	Yield
With ethanol

sodium ethanolate (141-52-6) + quinhydrone (106-34-3) → 1,4-benzosemiquinone sodium salts (23686-88-6)

Conditions	Yield
With diethyl ether; ethanol

quinhydrone (106-34-3) → 2-bromobenzene-1,4-diol (583-69-7)

Conditions	Yield
With tetrachloromethane; bromine

quinhydrone (106-34-3) → hydroquinone (123-31-9)

Conditions	Yield
With water; iron; iron(II) sulfate
With manganese Hydroxide; water; iron(II) sulfate
With potassium chloride; zinc at 65 - 75℃;

quinhydrone (106-34-3) → hydroquinone (123-31-9) + p-benzoquinone (106-51-4)

Conditions	Yield
With water

Upstream product

• 75-07-0 acetaldehyde 
• 106-51-4 p-benzoquinone 
• 4317-06-0 tetraethylphosphonium iodide 
• 64-19-7 acetic acid 
• 634-35-5 N-ethylquinolinium iodide 
• 122-37-2 4-anilinophenol 
• 64-17-5 ethanol 
• 509-14-8 tetranitromethane 
• 123-31-9 hydroquinone 
• 6246-98-6 N,N'-diphenyl-1,4-phenylenediamine 
• 918-37-6 hexanitroethane 
• 3131-54-2 4-methylbenzo-1,2-quinone 
• 697-91-6 2,6-dichloro-1,4-benzoquinone 
• 434-84-4 bianthronyl 

Downstream Products

• 133-37-9 DL-tartaric acid 
• 100867-36-5 N-(4-((2,5-dihydroxyphenyl)sulfonyl)phenyl)acetamide 
• 23686-88-6 1,4-benzosemiquinone sodium salts 
• 123-31-9 hydroquinone 
• 87970-37-4 2,5-dimethyl-1,4-benzoquinone and 2 1,4-hydroquinone 
• 106-51-4 p-benzoquinone 
• 583-69-7 2-bromobenzene-1,4-diol 

Related news

Electron-selective Quinhydrone (cas 106-34-3) passivated back contact for high-efficiency silicon/organic heterojunction solar cells08/19/2019

Interfacial properties play a critical role in the dynamic process of carrier transport in dopant-free silicon (Si) heterojunction solar cells (HSCs), based on the poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS). In this study, we use quinhydrone (QHY) to engineer the interfa...detailed

Relevant articles and documents

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Electrocrystallization of Quinhydrone

Quinhydrone crystals were deposited at 2.0 V vs.Ag onto SnO2-coated glass substrates from aqueous solutions of hydroquinone in the presence of NaCl, HCl, or NaOH. The crystals were observed with backscattered image SEM, and characterized with X-ray diffraction and IR spectroscopy. In situ visible absorption spectra were measured and a mechanism of deposition is discussed.

Process for the preparation of quinhydrones

Disclosed is a process for the preparation of quinhydrones by the catalytic oxidation of aromatic diols with a peroxide in the presence of a catalyst system comprising a cerium carboxylate and a cupric carboxylate.