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533-73-3

Basic Information
CAS No.: 533-73-3
Name: 1,2,4-Benzenetriol
Article Data: 79
Molecular Structure:
Molecular Structure of 533-73-3 (1,2,4-Benzenetriol)
Formula: C6H6O3
Molecular Weight: 126.112
Synonyms: 1,2,4-Trihydroxybenzene;1,3,4-Benzenetriol;1,3,4-Trihydroxybenzene;2,5-Dihydroxyphenol;2-Hydroxy-1,4-hydroquinone;2-Hydroxy-p-benzohydroquinone;2-Hydroxyhydroquinone;4-Hydroxycatechol;HHQ;Hydroxyhydroquinone;NSC 2818;
EINECS: 208-575-1
Density: 1.488
Melting Point: 140 ºC
Boiling Point: 132.9 °C at 760 mmHg
Flash Point: 34.2 °C
Solubility: freely soluble in water
Appearance: Gray powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-37/38-41-36/37/38-20/21/22
Safety: 26-39-36/37/39-22
PSA: 60.69000
LogP: 0.80340
Synthetic route
613-03-6

1,2,4-triacetoxybenzene

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 7h; Reagent/catalyst; Reflux;98%
With hydrogenchloride; methanol
With acetic acid
95-01-2

2,4-Dihydroxybenzaldehyde

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.833333h; Dakin Phenol Oxidation; Green chemistry;96%
With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h;85%
1190844-34-8

(4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
In water at 170℃; for 2h; Inert atmosphere;93%
7647-01-0

hydrogenchloride

187221-63-2

triphenylantimony m-hydroxy-o-phenylenedioxide

A

533-73-3

1,2,4-Trihydroxybenzene

B

594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

Conditions
ConditionsYield
heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene;A 78%
B 86%
530-59-6

trans-3,5-dimethoxy-4-hydroxycinnamic acid

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere;57%
305-01-1

aesculetin

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Sealed tube; Inert atmosphere;56%
108-46-3

recorcinol

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature;42%
With 2,6-dichloroquinone-4-chloroimide; sodium acetate; acetic acid
With water for 0.166667h;
123-31-9

hydroquinone

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature;39%
With sodium hydroxide
With oxygen; iron(III) In water pH=2.0; Kinetics; hydroxylation; Electrochemical reaction;
With titanium(IV) oxide In water at 30℃; Mechanism; Time; UV-irradiation;
Multi-step reaction with 3 steps
1: iodine; dihydrogen peroxide / water; sulfuric acid / 30 - 50 °C
2: sulfuric acid / 0.5 h / 25 - 50 °C
3: hydrogenchloride; water / methanol / 7 h / Reflux
View Scheme
78963-40-3

2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With phosphoric acid In water at 125℃; for 12h;39%
In water at 170℃; for 2h; Product distribution / selectivity; Inert atmosphere; Autoclave;95 %Chromat.
99-50-3

3,4-Dihydroxybenzoic acid

A

2474-72-8

hydroxyquinone

B

533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With air; methylene blue In methanol for 12h; Product distribution; Mechanism; Irradiation;A 15%
B 35%
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    Name: 1,2,4-Trihydroxybenzene Synonyms: 1,2,4-Benzentril CAS: 533-73-3 MF: C6H6O3 Appearance:White powder or crystalline powder Storage:Store in cool and dry place, away from sun light. Package: 25kgs/drum Application:Agrochemical Intermediates,

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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

The 1,2,4-Benzenetriol with cas registry number of 533-73-3 is also known as Hydroxyhydroquinone; 1,2,4-Trihydroxybenzene. Both its systematic name and IUPAC name are the same which is called benzene-1,2,4-triol. This chemical is a kind of categories in Aromatic Hydrocarbons (substituted) & Derivatives; Aromatics Compounds; Metabolites & Impurities. It is stable under normal temperatures and pressures with appearance of gray powder. It is also sensitive to air and incompatibl with oxidizing materials, strong oxidizing agents, strong oxidizing agents, bases, acid chlorides, acids, water reactive substances, acid anhydrides. In addition, it has EINECS registry number which is 208-575-1.

The physical properties about this chemical are: (1)ACD/LogP: 0.06; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.06; (4)ACD/LogD (pH 7.4): 0.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 25.61; (8)ACD/KOC (pH 7.4): 25.41; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.676; (13)Molar Refractivity: 31.89 cm3; (14)Molar Volume: 84.7 cm3; (15)Surface Tension: 78.6 dyne/cm; (16)Density: 1.488 g/cm3; (17)Flash Point: 176.9 °C; (18)Enthalpy of Vaporization: 60.03 kJ/mol; (19)Boiling Point: 334.5 °C at 760 mmHg; (20)Vapour Pressure: 6.57E-05 mmHg at 25°C.

Preparation of 1,2,4-Benzenetriol: it can be made by benzene-1,3-diol by using reagents H2O2, <(Ce2(p-tert-butylcalix (8) arene)) (Me2SO) 5> * 2Me2SO and solvent acetonitrile. The reaction occurs at ambient temperature for 5 hours with 42% yield.

Uses of 1,2,4-Benzenetriol: it can be used to prepare 4-hydroxycyclohexane-1,3-dione. The reaction will need reagents KOH, H2, catalyst 10percentPdCl2 / C and solvent Methanol at temperature 100 ℃ under pressure 60800. It will need 3 hours with 70% yield.

When you are using this chemical, please be cautious about it as the following:
Poison by subcutaneous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. As a chemical, it is harmful by inhalation, in contact with skin and if swallowed and irritating to eyes, respiratory system and skin. Therefore, when you are using this chemical, wear suitable protective clothing, gloves and eye/face protection, and do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1cc(O)c(O)cc1;
(2)InChI: InChI=1/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H;
(3)InChIKey: GGNQRNBDZQJCCN-UHFFFAOYAX

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 25mg/kg (25mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
National Technical Information Service. Vol. OTS0540939,
mouse LD50 subcutaneous 122mg/kg (122mg/kg)   Industrial Health. Vol. 5, Pg. 143, 1967.
mouse LDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0540939,