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CAS No.: | 123-31-9 |
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Name: | Hydroquinone |
Article Data: | 977 |
Cas Database | |
Molecular Structure: | |
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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: |
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Risk Codes: | 22-40-41-43-50-68 |
Safety: | 26-36/37/39-61 |
Transport Information: | UN 2662 |
PSA: | 40.46000 |
LogP: | 1.09780 |
Conditions | Yield |
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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% |
Conditions | Yield |
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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; |
Conditions | Yield |
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With hydrogen In tetrahydrofuran; carbon dioxide at 50℃; under 75007.5 Torr; gas-expanded solution; | 100% |
dimethanesulfonate hydroquinone
hydroquinone
Conditions | Yield |
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With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction; | 100% |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
hydrazine hydroquinone complex
4-hydroxy-benzaldehyde
A
bis(4-hydroxybenzylidene)hydrazine
B
hydroquinone
Conditions | Yield |
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at 25 - 30℃; for 1h; Product distribution; Further Variations:; Reaction partners; Reaction types; Condensation; solid state, in ball mill; | A 98% B n/a |
(p-hydroxyphenyl)boronic acid
hydroquinone
Conditions | Yield |
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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% |
Conditions | Yield |
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With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry; | 98% |
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.
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
For occupational chemical analysis use NIOSH: Hydroquinone, 5004.
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 |
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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. |