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1,2,4-Benzenetriol

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1,2,4-Benzenetriol manufacturers

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1,2,4-Benzenetriol Basic information
Product Name:1,2,4-Benzenetriol
Synonyms:OXYHYDROQUINONE;1,2,4-BENZENETRIOL;1,3,4-Benzenetriol;1,3,4-Trihydroxybenzene;2,5-Dihydroxyphenol;2-Hydroxy-1,4-hydroquinone;Hydroquinone, hydroxy-;hydroxy-hydroquinon
CAS:533-73-3
MF:C6H6O3
MW:126.11
EINECS:208-575-1
Product Categories:Aromatic Hydrocarbons (substituted) & Derivatives;Aromatics Compounds;Aromatics;Metabolites & Impurities;bc0001
Mol File:533-73-3.mol
1,2,4-Benzenetriol Structure
1,2,4-Benzenetriol Chemical Properties
Melting point 140 °C (subl.) (lit.)
Boiling point 194.21°C (rough estimate)
density 1.45 g/cm3 (20℃)
refractive index 1.5627 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMSO (Sparingly), Methanol (Slightly)
form Solid
pka9.58±0.10(Predicted)
color Plates from Et2O
Water Solubility freely soluble
Sensitive Air Sensitive
Merck 14,1073
BRN 2042863
Stability:Light Sensitive, Moisture Sensitive
CAS DataBase Reference533-73-3(CAS DataBase Reference)
NIST Chemistry Reference1,2,4-Benzenetriol(533-73-3)
EPA Substance Registry System1,2,4-Benzenetriol (533-73-3)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-37/38-41-36/37/38-20/21/22
Safety Statements 26-39-36/37/39-22
WGK Germany 3
RTECS DC4200000
Hazard Note Irritant/Keep Cold/Air Sensitive
TSCA Yes
HS Code 2907 29 00
Toxicityoms-hmn:lym 50 mmol/L CNREA8 45,2471,85
MSDS Information
ProviderLanguage
Hydroxyhydroquinone English
SigmaAldrich English
ACROS English
ALFA English
1,2,4-Benzenetriol Usage And Synthesis
Chemical PropertiesGray powder
Physical properties1,2,4-Benzenetriol forms colorless platelets or prisms that quickly colorize in air. It is soluble in water and polar solvents, and slightly soluble in chloroform and carbon disulfide.
Uses1,2,4-Trihydroxybenzene is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.It is used as a metabolite of benzene.
DefinitionChEBI: Benzene-1,2,4-triol is a benzenetriol carrying hydroxy groups at positions 1, 2 and 4. It has a role as a mouse metabolite.
Production Methods1,2,4-Benzenetriol is synthesized by hydrolysis of 1,2,4-triacetoxybenzene, which is prepared by the acid-catalyzed reaction of p-benzoquinone with acetic anhydride.
Other production methods for 1,2,4-Benzenetriol are oxidation of resorcinol with hydrogen peroxide and Dakin oxidation of 2,4- or 3,4-dihydroxybenzaldehydes or 2,4- or 3,4-dihydroxyacetophenones with alkaline hydrogen peroxide solution.
General Description1,2,4-Benzenetriol is also known as hydroxyhydroquinone. It is an intermediary metabolite of benzene that is present in roasted coffee beans. It is mutagenic and it causes cleaving of DNA single strands by the generation of reactive oxygen species.
Chemical Reactivity1,2,4-Benzenetriol is, like other phenols, a strong reducing agent. Its basic aqueous solution absorbs gaseous oxygen to produce black precipitates of the humic acid type. 1,2,4-Benzenetriol shows typical reactions of phenols. Derivatives of the tautomeric keto form are also known: halogenation of hydroxyhydroquinone, for example, gives 1,2,5,5-tetrahalocyclohexene-3,4,6-trione. Condensation with ethylacetoacetate produces dihydroxycoumarin; reaction with phthalic anhydride yields hydroxyhydroquinonephthalein. Monosubstitution of a hydroxy group by an amino group occurs easily at room temperature and gives 2,4-dihydroxyaniline.
Safety ProfilePoison by subcutaneous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification MethodsCrystallise the triol from Et2O or Et2O/EtOH, and dry it in a vacuum. The picrate forms orange-red needles m 96o. [Beilstein 6 H 1087, 6 I 541, 6 II 1071, 6 III 6276.]
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