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

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

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

Toxicity

oms-hmn:lym 50 mmol/L CNREA8 45,2471,85

MSDS

• Language:English Provider:Hydroxyhydroquinone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,2,4-Benzenetriol Usage And Synthesis

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.

Uses

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.

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.]

1,2,4-Benzenetriol(533-73-3)Related Product Information

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