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HomeProduct name list1,2,4-Benzenetriol

1,2,4-Benzenetriol

Synonym(s):1,2,4-Trihydroxybenzene;2-Heptyl-4-quinolone;Hydroxyhydroquinone

  • CAS NO.:533-73-3
  • Empirical Formula: C6H6O3
  • Molecular Weight: 126.11
  • MDL number: MFCD00002198
  • EINECS: 208-575-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 18:15:48
1,2,4-Benzenetriol Structural

What is 1,2,4-Benzenetriol?

Chemical properties

Gray powder

Physical properties

1,2,4-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.

The Uses of 1,2,4-Benzenetriol

A metabolite of benzene.

The Uses of 1,2,4-Benzenetriol

1,2,4-Trihydroxybenzene is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.It is used as a metabolite of benzene.

What are the applications of Application

1,2,4-Benzenetriol is a metabolite of benzene

Definition

ChEBI: 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 Methods

1,2,4-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 Description

1,2,4-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 Reactivity

1,2,4-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 Profile

Poison by subcutaneous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise 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.]

Properties of 1,2,4-Benzenetriol

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
pka 9.58±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 Reference 533-73-3(CAS DataBase Reference)
NIST Chemistry Reference 1,2,4-Benzenetriol(533-73-3)
EPA Substance Registry System 1,2,4-Benzenetriol (533-73-3)

Safety information for 1,2,4-Benzenetriol

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H318:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for 1,2,4-Benzenetriol

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