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106-51-4

Basic Information
CAS No.: 106-51-4
Name: 1,4-Benzoquinone
Article Data: 904
Molecular Structure:
Molecular Structure of 106-51-4 (1,4-Benzoquinone)
Formula: C6H4O2
Molecular Weight: 108.097
Synonyms: p-Benzoquinone(8CI);1,4-Cyclohexadienedione;Chinone;NSC 36324;PBQ 2;Stearer PBQ;p-Quinone;Quinone;
EINECS: 203-405-2
Density: 1.256 g/cm3
Melting Point: 113-115 ºC
Boiling Point: 174 ºC at 760 mmHg
Flash Point: 59.3 ºC
Solubility: 10 g/L (25 ºC) in water
Appearance: gold powder
Hazard Symbols: ToxicT,DangerousN,IrritantXi,FlammableF
Risk Codes: 23/25-36/37/38-50-20/21/22-11
Safety: 26-28-45-61-23-16
Transport Information: UN 2587 6.1/PG 2
PSA: 34.14000
LogP: 0.25060
Synthetic route
150-76-5

4-methoxy-phenol

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;100%
With copper(II) nitrate/zeolite H-Y Product distribution; Further Variations:; heating mode; times; microwave irradiation;100%
With manganese dioxide impregnated with nitric acid In dichloromethane for 0.5h; Ambient temperature;96%
123-31-9

hydroquinone

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.25h; Product distribution; Heating;100%
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature;100%
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.25h; Ambient temperature;100%
108-95-2

phenol

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With CuCl2 In acetonitrile100%
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 10h; Catalytic behavior; Inert atmosphere;99%
With manganese(IV) oxide; sulfuric acid; aniline at 10℃; for 1.5h;95%
123-31-9

hydroquinone

A

36831-87-5

diphenyl-2,5 furannedicarbaldehyde 3,4

B

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.3h; Heating;A 70%
B 100%
150-78-7

1,4-dimethoxybezene

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 4h;100%
With manganese dioxide impregnated with nitric acid In dichloromethane for 1.5h; Ambient temperature;93%
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1h;86%
2117-24-0

1,4-bis(trimethylsilyloxy)benzene

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 25℃; for 2h; Mechanism; relative reaction rate;99%
With quinolinium monofluorochromate(VI) In dichloromethane for 1h; Ambient temperature;98%
With dioxochloro(trimethylsiloxy)chromate(VI) In dichloromethane for 0.333333h; Ambient temperature;97%
99-93-4

4-Hydroxyacetophenone

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In acetonitrile at 80℃; for 0.75h; Baeyer-Villiger Ketone Oxidation; regioselective reaction;99%
106-50-3

1,4-phenylenediamine

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With sodium periodate In water at 20℃; for 0.166667h;98%
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.166667h;90%
With sulfuric acid; manganese triacetate In water at 35℃; Rate constant; Mechanism;
With dichromate anion
With manganese(IV) oxide; sulfuric acid
55-21-0

benzamide

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With iodobenzene; oxone; water In acetonitrile at 20℃;98%
With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.5h; Time; Solvent;80%
622-62-8

4-Ethoxyphenol

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 0.5h;97%
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;93%
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;92%
With Oxone In water; acetonitrile at 20℃; for 17h;79%
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    Water:0.5%Max; Residue on ignition:0.05%Max; Melting point: 112-116℃Appearance:yellow crystals

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A.,49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 ,1977,p. 255.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. Community Right-To-Know List. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 0.1 ppm
ACGIH TLV: TWA 0.1 ppm
DFG MAK: 0.1 ppm (0.45 mg/m3)
DOT Classification:  6.1; Label: Poison

Specification

The 1,4-Benzoquinone, with the CAS registry number 106-51-4,is also known as 2,5-Cyclohexadiene-1,4-dione; Quinone; Quinone; p-Benzoquinone 98+ % (dried); 2,5-Cyclohexadiene-1,4-dione. It belongs to the product categories of Charge Transfer Complexes for Organic Metals;Benzoquinones;Functional Materials.This chemical's molecular formula is C6H4O2 and molecular weight is 108.09.Its EINECS number is 203-405-2. What's more,Its systematic name is p-Benzoquinone.It is a yellowish-colored crystalline solid with a pungent, irritating odor. Poisonous by ingestion or inhalation of vapors. May severely damage skin, eyes and mucous membranes. Used to make dyes and as a photographic chemical.

Physical properties about 1,4-Benzoquinone are:
(1)ACD/LogP:  0.394; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  0.39; (4)ACD/LogD (pH 7.4):  0.39; (5)ACD/BCF (pH 5.5):  1.17; (6)ACD/BCF (pH 7.4):  1.17; (7)ACD/KOC (pH 5.5):  39.05; (8)ACD/KOC (pH 7.4):  39.05; (9)#H bond acceptors:  2; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.543; (13)Molar Refractivity:  27.139 cm3; (14)Molar Volume:  86.036 cm3; (15)Surface Tension:  47.8059997558594 dyne/cm; (16)Density:  1.256 g/cm3; (17)Flash Point:  59.33 °C; (18)Enthalpy of Vaporization:  41.035 kJ/mol; (19)Boiling Point:  174.004 °C at 760 mmHg; (20)Vapour Pressure:  1.23199999332428 mmHg at 25°C.

Use of 1,4-Benzoquinone:
1,4-Benzoquinone is used as a dye and pharmaceutical intermediate, rubber antioxidant, inhibitor, anti-oxidants, reagent,oxidant. It is also used in organic synthesis such as for the synthesis of hydroquinone.

Preparation of 1,4-Benzoquinone:
1,4-Benzoquinone can be prepared by the oxidation of benzene, aniline, and hydroquinone by a miscellany of oxidizing agents. The oxidation of hydroquinone is rapid and convenient and therefore desirable for the laboratory. 1,4-Benzoquinone can be prepared from hydroquinone via a number of oxidation methods. One such method makes use of hydrogen peroxide as the oxidizer and iodine or an iodine salt as a catalyst for the oxidation occurring in a polar solvent; e.g. isopropyl alcohol.
When heated to its melting point, the product sublimates at atmospheric pressure, and, when prepared from hydroquinone, the substrate boils at a significantly higher temperature than 1,4-benzoquinones melting point, allowing for an effective separation of the two. Impure samples are often dark-colored due to the presence of quinhydrone (1:1 complex of quinone with hydroquinone). When prepared by methods involving iodine (an element with a characteristically intense stain), traces of iodine contamination in the product may also darken its appearance. 1,4-Benzoquinone's high vapour pressure at room temperature means that containers should be well sealed to prevent its gradual sublimation into the atmosphere whilst in storage.

You can still convert the following datas into molecular structure:
(1)SMILES:C1=CC(=O)C=CC1=O;
(2)Std. InChI:InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H;
(3)Std. InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N;

Safety Information of 1,4-Benzoquinone:
The 1,4-Benzoquinone is Toxic by inhalation and if swallowed. 
It is irritating to eyes, respiratory system and skin  and Harmful by inhalation, in contact with skin and if swallowed.So after contact with skin, wash immediately with plenty of water (to be specified by the manufacturer).In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And it is very Toxic to aquatic organisms ,so it should be avoid release to the environment. Refer to special instructions safety data sheet.Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .This chemical is highly Flammable,keep away from sources of ignition - No smoking.

The toxicity data of 1,4-Benzoquinone as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 subcutaneous 296mg/kg (296mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 25, 1982.
mouse LD50 intraperitoneal 8500ug/kg (8.5mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Biochemical Pharmacology. Vol. 12, Pg. 885, 1963.
mouse LD50 oral 25mg/kg (25mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0571885,
mouse LD50 subcutaneous 93800ug/kg (93.8mg/kg)   Zeitschrift fuer die Gesamte Innere Medizin und Ihre Grenzgebiete. Vol. 2, Pg. 333, 1947.
rat LD50 intraperitoneal 30mg/kg (30mg/kg)   Pharmaceutical Bulletin. Vol. 3, Pg. 337, 1955.
rat LD50 intravenous 25mg/kg (25mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
rat LD50 oral 130mg/kg (130mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
rat LD50 unreported 5600ug/kg (5.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Russian Pharmacology and Toxicology Vol. 41, Pg. 146, 1978.