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CAS No.: | 533-73-3 |
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Name: | 1,2,4-Benzenetriol |
Article Data: | 79 |
Molecular Structure: | |
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: | Xn |
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 |
Conditions | Yield |
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With hydrogenchloride; water In methanol for 7h; Reagent/catalyst; Reflux; | 98% |
With hydrogenchloride; methanol | |
With acetic acid |
Conditions | Yield |
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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% |
(4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one
1,2,4-Trihydroxybenzene
Conditions | Yield |
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In water at 170℃; for 2h; Inert atmosphere; | 93% |
hydrogenchloride
triphenylantimony m-hydroxy-o-phenylenedioxide
A
1,2,4-Trihydroxybenzene
B
triphenylantimony dichloride
Conditions | Yield |
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heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene; | A 78% B 86% |
Conditions | Yield |
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With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere; | 57% |
Conditions | Yield |
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With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Sealed tube; Inert atmosphere; | 56% |
Conditions | Yield |
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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; |
Conditions | Yield |
---|---|
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 |
2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one
1,2,4-Trihydroxybenzene
Conditions | Yield |
---|---|
With phosphoric acid In water at 125℃; for 12h; | 39% |
In water at 170℃; for 2h; Product distribution / selectivity; Inert atmosphere; Autoclave; | 95 %Chromat. |
Conditions | Yield |
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With air; methylene blue In methanol for 12h; Product distribution; Mechanism; Irradiation; | A 15% B 35% |
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, |