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123-31-9

Basic Information
CAS No.: 123-31-9
Name: Hydroquinone
Article Data: 977
Cas Database
Molecular Structure:
Molecular Structure of 123-31-9 (Hydroquinone)
Formula: C6H6O2
Molecular Weight: 110.112
Synonyms: p-Dihydroxybenzene;Tecquinol;Benzohydroquinone;Benzoquinol;1,4-Dihydrobenzoquinone;1, 4-Dihydroxy-benzol;Idrochinone;1,4-Dihydroxy-benzeen;Diak 5;p-Hydroquinone;NCI-C55834;1, 4-Dihydroxybenzene;Benzene-1,4-diol;p-Dioxybenzene;Derma-Blanch;Hydroquinone (USP);p-Dioxobenzene;Usaf ek-356;1/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8;Tequinol;Hydrochinon (CZECH, POLISH);Quinol;Dihydroquinone;.alpha.-Hydroquinone;1,4-Diidrobenzene;Eldoquin;Eldoquin (TN);1,4-Benzenediol;Hydroquinol;p-Benzenediol;Phiaquin;4-Hydroxyphenol;1,4-Dihydroxybenzen;.beta.-Quinol;Benzene, p-dihydroxy-;Artra;Black and White Bleaching Cream;p-Hydroxyphenol;1,4-Dihydroxybenzene;Eldopaque;Hydroquinole;Tenox HQ;Hidroquinone;Arctuvin;p-dihydroxybenzene, hydroquinone;Hydroquinone,123-31-9;
EINECS: 204-617-8
Density: 1.275 g/cm3
Melting Point: 172-175 °C(lit.)
Boiling Point: 286 °C at 760 mmHg
Flash Point: 141.6 °C
Solubility: water: 70 g/L (20 °C)
Appearance: off-white powder or white needle-like crystals
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-40-41-43-50-68
Safety: 26-36/37/39-61
Transport Information: UN 2662
PSA: 40.46000
LogP: 1.09780
Synthetic route
106-51-4

p-benzoquinone

123-31-9

hydroquinone

Conditions
ConditionsYield
With nickel In tetrahydrofuran at 20℃; for 0.166667h; Reduction;100%
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile at 0℃; for 0.0833333h;99%
With hydrazine hydrate In acetonitrile at 20℃; for 18h; Irradiation;99%
103-16-2

4-Benzyloxyphenol

123-31-9

hydroquinone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 50℃; under 750.075 Torr; Reagent/catalyst; Flow reactor;100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 18h; Reagent/catalyst; chemoselective reaction;100%
With hydrogen In methanol at 20℃; for 6h; chemoselective reaction;100%
Multi-step reaction with 3 steps
1: potassium carbonate, potassium iodide / acetonitrile / 1 h / Heating
2: 84 percent / hydrogen / 10percent palladium on carbon / tetrahydrofuran; ethanol / 3 h / 760 Torr
3: 88 percent / hydrogen / 10percent palladium on carbon / ethanol / 15 h / 3040 Torr
View Scheme
With formic acid for 3h; Heating / reflux;
621-91-0

1,4-dibenzyloxybenzene

123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran; carbon dioxide at 50℃; under 75007.5 Torr; gas-expanded solution;100%
126150-65-0

dimethanesulfonate hydroquinone

123-31-9

hydroquinone

Conditions
ConditionsYield
With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction;100%
150-78-7

1,4-dimethoxybezene

123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry;98%
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;96%
With lithium triethylborohydride In tetrahydrofuran at 67℃; for 168h;90%
123-08-0

4-hydroxy-benzaldehyde

123-31-9

hydroquinone

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.666667h; Dakin Phenol Oxidation; Green chemistry;98%
With dihydrogen peroxide In water at 20℃; for 2h; Dakin Phenol Oxidation; Green chemistry;98%
With dihydrogen peroxide; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; sodium hydrogencarbonate In methanol; water at 20℃; for 24h; Reagent/catalyst; Dakin Phenol Oxidation; chemoselective reaction;97%
97108-34-4

hydrazine hydroquinone complex

123-08-0

4-hydroxy-benzaldehyde

A

5466-23-9

bis(4-hydroxybenzylidene)hydrazine

B

123-31-9

hydroquinone

Conditions
ConditionsYield
at 25 - 30℃; for 1h; Product distribution; Further Variations:; Reaction partners; Reaction types; Condensation; solid state, in ball mill;A 98%
B n/a
71597-85-8

(p-hydroxyphenyl)boronic acid

123-31-9

hydroquinone

Conditions
ConditionsYield
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;98%
With 1-carboxymethyl-3-methylimidazolium tetrachloroferrate; dihydrogen peroxide In neat (no solvent) at 20℃; for 0.116667h;95%
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;91%
2117-24-0

1,4-bis(trimethylsilyloxy)benzene

123-31-9

hydroquinone

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry;98%
106-51-4

p-benzoquinone

2633-66-1

2-mesitylmagnesium bromide

A

4-hydroxy-4-(2,4,6-trimethylphenyl)-2,5-cyclohexadiene

B

123-31-9

hydroquinone

C

108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran Grignard reaction;A 97%
B 3%
C 4%
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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. 155.(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) . Community Right-To-Know List. EPA Extremely Hazardous Substances List. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 2 mg/m3
ACGIH TLV: TWA 2 mg/m3; Animal Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (Hydroquinone) CL 2.0 mg/m3/15M
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Analytical Methods

For occupational chemical analysis use NIOSH: Hydroquinone, 5004.

Specification

1. Introduction of Hydroquinone
Hydroquinone, its CAS NO. is 123-31-9, the synonyms are Quinol; 1,4-Benzenediol; 1,4-Dihydroxybenzene. The IUPAC Name of it is benzene-1,4-diol.

2. Properties of Hydroquinone
Mol File: 123-31-9.mol
EINECS: 204-617-8
Melting Point: 172-175 °C(lit.)
Boiling point: 286 °C at 760 mmHg
Flash Point: 141.6 °C
Density: 1.275 g/cm3
Water Solubility: 70 g/L (20 ºC)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, oxygen, ferric salts. Light and air-sensitive. Discolours in air.
Index of Refraction: 1.612 
Molar Refractivity: 30.01 cm3 
Molar Volume: 86.2 cm3 
Surface Tension: 57.1 dyne/cm
Enthalpy of Vaporization: 54.61 kJ/mol
Vapour Pressure: 0.00157 mmHg at 25°C
XLogP3-AA: 0.6
H-Bond Donor: 2
H-Bond Acceptor: 2

3. Structure Descriptors of Hydroquinone
Canonical SMILES: C1=CC(=CC=C1O)O
InChI: InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H  
InChIKey: QIGBRXMKCJKVMJ-UHFFFAOYSA-N
Product Categories: Intermediates of Dyes and Pigments; Redox Catalysts (Environmentally-friendly Oxidation); Environmentally-friendly Oxidation; Synthetic Organic Chemistry; Aromatics.

4. Toxicity of Hydroquinone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 50mg/kg (50mg/kg)   National Technical Information Service. Vol. OTS0555537,
cat LDLo subcutaneous 50mg/kg (50mg/kg) BEHAVIORAL: TREMOR

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 72, Pg. 241, 1913.
dog LD50 oral 200mg/kg (200mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: NAUSEA OR VOMITING
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
dog LDLo intravenous 80mg/kg (80mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 162, 1955.
dog LDLo subcutaneous 100mg/kg (100mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 183, Pg. 319, 1936.
frog LDLo parenteral 190mg/kg (190mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
frog LDLo subcutaneous 190mg/kg (190mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 160, 1955.
guinea pig LD50 oral 550mg/kg (550mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
guinea pig LDLo intraperitoneal 200mg/kg (200mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 162, 1955.
guinea pig LDLo subcutaneous 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 162, 1955.
human LDLo oral 29mg/kg (29mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 321, 1969.
human TDLo oral 170mg/kg (170mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Annales de Medecine Legale. Criminologie, Police Scientifique et Toxicologie. Vol. 7, Pg. 79, 1927.
mammal (species unspecified) LD50 oral 480mg/kg (480mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 15, Pg. 136, 1979.
mammal (species unspecified) LD50 skin 5970mg/kg (5970mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD414-344,
mouse LD50 oral 245mg/kg (245mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 6, 1973.
mouse LD50 subcutaneous 182mg/kg (182mg/kg)   Zeitschrift fuer die Gesamte Innere Medizin und Ihre Grenzgebiete. Vol. 2, Pg. 333, 1947.
mouse LD50 unreported 150mg/kg (150mg/kg)   British Journal of Cancer. Vol. 6, Pg. 160, 1952.
pigeon LD50 oral 300mg/kg (300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: EXCITEMENT
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
rabbit LD50 intraperitoneal 125mg/kg (125mg/kg)   Ecotoxicology and Environmental Safety. Vol. 19, Pg. 327, 1990.
rabbit LD50 oral 200mg/kg (200mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
rabbit LDLo intravenous 100mg/kg (100mg/kg)   Agressologie. Revue Internationale de Physio-Biologie et de Pharmacologie Appliquees aux Effets de l'Agression. Vol. 3, Pg. 311, 1962.
rat LD50 intraperitoneal 170mg/kg (170mg/kg)   Ecotoxicology and Environmental Safety. Vol. 19, Pg. 327, 1990.
 
rat LD50 intravenous 115mg/kg (115mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 348, 1949.
rat LD50 oral 302mg/kg (302mg/kg)   National Technical Information Service. Vol. OTS0555537,
rat LD50 unreported 720mg/kg (720mg/kg)   Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972.
rat LDLo subcutaneous 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 162, 1955.

5. Safety Information of Hydroquinone
Hazard Codes: XnHarmful,NDangerous
Risk Statements: 22-40-41-43-50-68  
R22:Harmful if swallowed. 
R40:Limited evidence of a carcinogenic effect. 
R41:Risk of serious damage to the eyes. 
R50:Very toxic to aquatic organisms. 
R68:Possible risk of irreversible effects.
Safety Statements: 26-36/37/39-61
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: 2662
WGK Germany: 3
RTECS: MX3500000
HazardClass: 9
PackingGroup: III

6. Use of Hydroquinone
Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. In human medicine, hydroquinone is used as a topical application in skin whitening to reduce the color of skin as it does not have the same predisposition to cause dermatitis as Metol does. The disodium diphenolate salt of hydroquinone is used as an alternating comonomer unit in the production of the polymer PEEK. As a polymerization inhibitor, hydroquinone prevents polymerization of acrylic acid, methyl methacrylate, etc. Hydroquinone is also used as a raw material of herbicides, rubber antioxidants and dyestuffs.