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| CAS No.: | 123-31-9 |
|---|---|
| Name: | Hydroquinone |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn, N
|
| Risk Codes: | 22-40-41-43-50-68 |
| Safety: | 26-36/37/39-61 |
| Transport Information: | UN 2662 |
| PSA: | 40.46000 |
| LogP: | 1.09780 |
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| Conditions | Yield |
|---|---|
| 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 |
|---|---|
| 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 |
|---|---|
| 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 | Yield |
|---|---|
| With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction; | 100% |
| Conditions | Yield |
|---|---|
| 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 |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
|---|---|
| With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry; | 98% |
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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: Xn
,N
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.