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Quinhydrone

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Name

Quinhydrone

EINECS 203-387-6
CAS No. 106-34-3 Density 1.40
PSA 74.60000 LogP 1.34840
Solubility 4 g/L (20 °C) in water Melting Point 167-172 °C(lit.)
Formula C6H6O2.C6H4O2 Boiling Point 286 °C at 760 mmHg
Molecular Weight 218.209 Flash Point 141.6 °C
Transport Information UN 2811 6.1/PG 3 Appearance green crystalline powder
Safety 26-36-61-37/39-29 Risk Codes 22-36/37/38-50
Molecular Structure Molecular Structure of 106-34-3 (Quinhydrone) Hazard Symbols HarmfulXn, DangerousN
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);

Article Data 95

Quinhydrone Synthetic route

33802-06-1

di-tert-butyliminoxyl

4323-21-1

4-hydroxycyclohexa-2,5-dien-1-one

106-34-3

quinhydrone

Conditions
ConditionsYield
at -30℃;99%
108-95-2

phenol

106-34-3

quinhydrone

Conditions
ConditionsYield
With hydroquinone; p-benzoquinone; copper(l) chloride In acetonitrile94.1%
With mineral acid at 12 - 17℃; Oxydation;
105398-69-4

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

106-51-4

p-benzoquinone

A

3116-98-1

bicyclohexyl-3,6-diene-2,5-dione

B

106-34-3

quinhydrone

C

117749-44-7

3-cyclohexyl-2-(pyridine-2-thiyl)-1,4-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; Irradiation;A 7%
B n/a
C 83%
109276-74-6

(3,3-diphenylpropanoyloxy)-2-pyridinethione

106-51-4

p-benzoquinone

A

34708-59-3

1-(1,4-Benzochinonyl)-2,2-diphenylethan

B

106-34-3

quinhydrone

C

117749-43-6

3-(2,2-diphenylethyl)-2-(pyridine-2-thiyl)-1,4-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; Irradiation;A 7%
B n/a
C 80%
91534-05-3

N-(3,3-diphenylpropionyloxy)-pyridine-2-thione

106-51-4

p-benzoquinone

A

106-34-3

quinhydrone

B

117749-41-4

2-(1-Benzyl-2-phenyl-ethyl)-[1,4]benzoquinone

C

117749-45-8

3-(1,3-diphenylpropan-2-yl)-2-(pyridine-2-thiyl)-1,4-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; Irradiation;A n/a
B 10%
C 78%
89025-67-2

N-palmitoxy-2-pyridinethione

106-51-4

p-benzoquinone

A

41427-22-9

2-n-Pentadecyl-1,4-benzoquinone

B

106-34-3

quinhydrone

C

117749-42-5

3-(1-pentadecyl)-2-(pyridine-2-thiyl)-1,4-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; Irradiation;A 10%
B n/a
C 77%
123-31-9

hydroquinone

106-34-3

quinhydrone

Conditions
ConditionsYield
With at 50℃; for 1h; Irradiation; solid state;64%
With sodium sulfate Oxydation;
With sulfuric acid at 0℃; Oxydation; unter Verwendung von Wechselstrom;
108-95-2

phenol

A

106-34-3

quinhydrone

B

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With 5,10,15,20-tetrakis(4-sulfophenyl)porphine; oxygen In water for 5h; Mechanism; Time; Solvent; Irradiation;A n/a
B 8.9%
2350-01-8

4-aminotriphenylamine

A

6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

B

106-34-3

quinhydrone

Conditions
ConditionsYield
With ethanol
488-73-3

(+)-proto-quercitol

A

106-34-3

quinhydrone

B

123-31-9

hydroquinone

C

106-51-4

p-benzoquinone

Conditions
ConditionsYield
at 280 - 290℃; im Vakuum;

Quinhydrone Consensus Reports

Reported in EPA TSCA Inventory.

Quinhydrone Specification

Quinhydrone(106-34-3) also can be called 2,5-Cyclohexadiene-1,4-dione compd with 1,4-benzenediol (1:1) and 1,4-Benzoquinone - 1,4-benzenediol (1:1). It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should  flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. In addition, Quinhydrone is moisture sensitive with air and light, and can be stable under normal temperature and pressure conditions. It is not compatible with strong oxidizing agents, and you must not take it with light, exposure to air, excess heat and incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon dioxide, carbon monoxide.

Physical properties about Quinhydrone are: (1)ACD/LogP: 0.644; (2)ACD/LogD (pH 5.5): 0.64; (3)ACD/LogD (pH 7.4): 0.64; (4)ACD/BCF (pH 5.5):1.82; (5)ACD/BCF (pH 7.4): 1.82; (6)ACD/KOC (pH 5.5): 53.40; (7)ACD/KOC (pH 7.4): 53.33; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Flash Point: 141.6 °C; (12)Enthalpy of Vaporization: 54.61 kJ/mol; (13)Boiling Point: 286 °C at 760 mmHg; (14)Vapour Pressure: 0.00157 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Avoid release to the environment. Refer to special instructions safety data sheet;
4. Wear suitable protective clothing and eye/face protection;
5. Do not empty into drains;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H6O2.C6H4O2/c2*7-5-1-2-6(8)4-3-5/h1-4,7-8H;1-4H;
(2)InChIKey=BDJXVNRFAQSMAA-UHFFFAOYSA-N;
(3)Smilesc1(ccc(O)cc1)O.C1(C=CC(=O)C=C1)=O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 100mg/kg (100mg/kg)   Revue Belge de Pathologie et de Medecine Experimentale. Vol. 22, Pg. 1, 1952.
mouse LDLo subcutaneous 100mg/kg (100mg/kg)   Revue Belge de Pathologie et de Medecine Experimentale. Vol. 22, Pg. 1, 1952.
rat LD50 intravenous 35mg/kg (35mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
rat LD50 oral 225mg/kg (225mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.

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