Conditions | Yield |
---|---|
With sodium dithionite In diethyl ether; water | 100% |
With sodium dithionite In diethyl ether; water at 20℃; | 100% |
With hydrogen In isopropyl alcohol at 110℃; under 7500.75 Torr; Reagent/catalyst; Autoclave; | 98% |
peracetic acid
2,3,6-trimethylphenol
A
2,3,5-Trimethyl-1,4-benzoquinone
B
Duroquinone
C
Trimethylhydroquinone
D
pentamethylphenol
E
1-methoxy-2,3,6-trimethylbenzene
F
2,3,6-trimethylphenyl acetate
Conditions | Yield |
---|---|
sulfuric acid at 50℃; for 0.5h; Mechanism; Thermodynamic data; effect of catalysts; | A 99.7% B 0.04% C 0.01% D 0.01% E 0.03% F 0.04% |
Conditions | Yield |
---|---|
With hydrogen; sodium carbonate at 80℃; | 94.7% |
2,6,6-trimethyl-1,4-cyclohexanedione
acetic anhydride
A
Trimethylhydroquinone
B
trimethylpyrocatechol
Conditions | Yield |
---|---|
Stage #1: 2,6,6-trimethyl-1,4-cyclohexanedione; acetic anhydride With sulfuric acid; acetic acid at 50℃; for 2h; Stage #2: With water for 3h; Heating / reflux; | A 88.5% B n/a |
Conditions | Yield |
---|---|
Stage #1: 1,2,4-Trimethylbenzene With formic acid; dihydrogen peroxide; calcium chloride at 50 - 90℃; for 5h; Stage #2: With sodium dithionite In water at 45℃; for 2h; Temperature; Reagent/catalyst; | 85.6% |
With peracetic acid; sodium disulfite 1) acetic acid, 70 deg C, 1 h; 2) water, 20 deg C, 0.5 h.; Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: sodium bromide; sulfuric acid; iron(II) sulfate; iodine; dihydrogen peroxide / dichloromethane; water / 0 °C 2: potassium dichromate; sulfuric acid; copper(II) sulfate / water; acetonitrile / 45 °C 3: sodium carbonate; hydrogen / 80 °C View Scheme |
Trimethylhydroquinone
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide In methanol; water at 17 - 35℃; Product distribution / selectivity; Dakin Reaction; | 85% |
peracetic acid
2,3,5-trimethylphenol
A
2,3,5-Trimethyl-1,4-benzoquinone
B
Trimethylhydroquinone
C
2,3,5-trimethyl-1,6-benzoquinone
D
2,3,5-trimethylanisole
E
1-acetoxy-2,3,5-trimethylbenzene
Conditions | Yield |
---|---|
sulfuric acid at 50℃; for 0.5h; Mechanism; Thermodynamic data; effect of catalysts; | A 67.15% B 0.15% C n/a D 0.03% E 0.04% F 32.03% |
Conditions | Yield |
---|---|
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h; | A n/a B 64% |
Trimethylhydroquinone
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 50℃; | 62% |
1,2,4-Trimethylbenzene
A
2,4-dimethylbenzyl alcohol
B
Trimethylhydroquinone
C
2,4,5-trimethylphenol
D
2,5-dimethylbenzyl alcohol
Conditions | Yield |
---|---|
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction; | A 31% B 12% C 34% D 12% |
1,2,4-Trimethylbenzene
A
2,4-dimethylbenzyl alcohol
B
Trimethylhydroquinone
C
2,4,5-trimethylphenol
D
2,3,5-trimethylphenol
E
2,5-dimethylbenzyl alcohol
Conditions | Yield |
---|---|
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W, I401M mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; | A 17% B 32% C 31% D 7% E 7% |
1,2,4-Trimethylbenzene
A
2,4-dimethylbenzyl alcohol
B
Trimethylhydroquinone
C
2,4,5-trimethylphenol
D
2,3,6-trimethylphenol
E
2,3,5-trimethylphenol
F
2,5-dimethylbenzyl alcohol
Conditions | Yield |
---|---|
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W, A330F, I401M mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction; | A 25% B 23% C 28% D 5% E 8% F 9% |
2-(2,4,6-trimethylphenyl)quinoline
Trimethylhydroquinone
Conditions | Yield |
---|---|
With sodium hydroxide |
4-Hexadecyloxy-2,3,6-trimethyl-phenol
Trimethylhydroquinone
Conditions | Yield |
---|---|
at 350 - 380℃; |
1-allyl-1-hydroxy-2,3,5-trimethylcyclohexa-2,4-dien-4-one
A
2,3,5-trimethyl-6-prop-2-enylbenzene-1,4-diol
B
Trimethylhydroquinone
C
5-allyl-2,3,5-trimethylcyclohex-2-ene-1,4-dione
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 1h; Product distribution; -73 deg C to 20 deg C; other reagents, temperature; | A 44 % Spectr. B 9 % Spectr. C 47 % Spectr. |
1-allyl-1-hydroxy-2,3,6-trimethylcyclohexa-2,4-dien-4-one
A
2,3,5-trimethyl-6-prop-2-enylbenzene-1,4-diol
B
Trimethylhydroquinone
Conditions | Yield |
---|---|
In dichloromethane for 8h; Heating; | A 80 % Spectr. B 5 % Spectr. |
2,3,5-Trimethyl-1,4-benzoquinone
2-p-tolyl-thio-3,5-trimethylhydroquinone
A
Trimethylhydroquinone
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 24℃; Equilibrium constant; further compound; | |
With sodium acetate In methanol; water at 24℃; Equilibrium constant; |
2,3,5-Trimethyl-1,4-benzoquinone
2,3,5-trimethyl-6-phenylsulfonylhydroquinone
A
Trimethylhydroquinone
B
2,3,5-trimethyl-6-phenylsulfonyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 24℃; Equilibrium constant; |
trimethyl-1,4-benzoquinone radical anion
A
2,3,5-Trimethyl-1,4-benzoquinone
B
Trimethylhydroquinone
Conditions | Yield |
---|---|
In water at 22℃; Rate constant; |
4-hydroxy-2,4,6-trimethyl-cyclohexa-2,5-dienone
Trimethylhydroquinone
4-hydroxy-2,4,6-trimethyl-cyclohexa-2,5-dienone
Trimethylhydroquinone
2-Bromo-3,5,6-trimethyl-hydroquinone
A
Trimethylhydroquinone
B
2,5-dihydroxy-3,4,6-trimethyl-benzaldehyde
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) THF, 5-15 deg C, sonication, 2 h, 2.) r.t., several hours; Yield given. Multistep reaction. Yields of byproduct given; |
2-Bromo-3,5,6-trimethyl-hydroquinone
A
Trimethylhydroquinone
B
2,3,5-Trimethyl-6-methylsulfanyl-benzene-1,4-diol
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) THF, 5-15 deg C, sonication, 2 h, 2.) r.t., several hours; Yield given. Multistep reaction. Yields of byproduct given; |
2,3,5-Trimethyl-1,4-benzoquinone
A
Trimethylhydroquinone
B
2-hydroxy-3,5,6-trimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
In water at 24℃; Quantum yield; Further Variations:; Solvents; UV-irradiation; |
2,3,6-trimethylphenol
A
2,3,5-Trimethyl-1,4-benzoquinone
B
Trimethylhydroquinone
Conditions | Yield |
---|---|
With dihydrogen peroxide; copper hydroxyphosphate In water; acetonitrile at 80℃; for 2h; | |
With dihydrogen peroxide; silica-supported P catalyst In acetonitrile at 80℃; for 2h; Product distribution; Further Variations:; Catalysts; |
acetic acid 3,6-dimethyl-2-oxo-cyclohex-3-enyl ester
Trimethylhydroquinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / tetrahydrofuran; diethyl ether 2: 64 percent / PCC; SiO2 / CH2Cl2 / 1 h / 20 °C View Scheme |
2,5-dimethyl-cyclohex-2-enone
Trimethylhydroquinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 70 percent / toluene / 4 h / Heating 2: 75 percent / tetrahydrofuran; diethyl ether 3: 64 percent / PCC; SiO2 / CH2Cl2 / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature; | 100% |
With pyridine; 3-carboxypyridinium dichromate In dichloromethane for 0.333333h; Ambient temperature; | 100% |
With dihydrogen peroxide In acetic acid | 100% |
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide In water; acetic acid at 40℃; for 5h; | 100% |
Multi-step reaction with 4 steps 1: Py 2: NH3 / methanol; benzene 3: NBS / methanol 4: NBS / ethanol; CHCl3 View Scheme |
Conditions | Yield |
---|---|
With pyridine; 3-carboxypyridinium dichromate In dichloromethane for 0.333333h; Product distribution; Ambient temperature; other reagents and ratio of reagents; | 100% |
Trimethylhydroquinone
methyl iodide
1,4-dimethoxy-2,3,5-trimethyl-benzene
Conditions | Yield |
---|---|
Stage #1: Trimethylhydroquinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h; | 100% |
Stage #1: Trimethylhydroquinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2.75h; | 89% |
With potassium carbonate In butanone at 65℃; for 72h; | 82% |
Conditions | Yield |
---|---|
In octane | 100% |
Conditions | Yield |
---|---|
With hydroxylated magnesium fluoride In 1,2-propylene cyclic carbonate; n-heptane at 100℃; for 3h; | 99.9% |
With nanoscopic partly hydroxylated AlF3-50 In n-heptane; propylene carbonate at 100℃; for 1h; Friedel-Crafts alkylation; | 99.9% |
With 2,6-di-tert-butyl-pyridine; trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide In n-heptane Heating; | 97% |
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In tetrachloromethane | 99.1% |
With hydrogenchloride; sodium dithionite; Zinc chloride In toluene | 99.8% |
With hydrogenchloride; zinc dibromide; zinc | 98.6% |
Trimethylhydroquinone
acetic acid
A
2,3,5-Trimethyl-1,4-benzoquinone
B
1,4-dimethoxy-2,3,5-trimethyl-benzene
C
2,3,5-trimethyl-1,4-hydroquinone diacetate
D
4-acetoxy-2,3,5-trimethylphenol
E
4-methoxy-2,3,5-trimethylphenol
Conditions | Yield |
---|---|
With peracetic acid at 50℃; for 0.25h; Product distribution; Kinetics; Thermodynamic data; | A 99.7% B 0.05% C 0.05% D 0.04% E 0.04% F 0.06% |
2-methylpropyl acetate
isophytol
Trimethylhydroquinone
Tocopherol
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In water; toluene | 99.6% |
With hydrogenchloride; Zinc chloride In water; toluene | 98.6% |
peracetic acid
Trimethylhydroquinone
A
2,3,5-Trimethyl-1,4-benzoquinone
B
1,4-dimethoxy-2,3,5-trimethyl-benzene
C
2,3,5-trimethyl-1,4-hydroquinone diacetate
D
4-acetoxy-2,3,5-trimethylphenol
E
4-methoxy-2,3,5-trimethylphenol
Conditions | Yield |
---|---|
sulfuric acid at 50℃; for 0.5h; Mechanism; Thermodynamic data; effect of catalysts; | A 99.5% B 0.05% C 0.06% D 0.05% E 0.04% F 0.07% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chloride; Zinc chloride In water; toluene | 99.2% |
With hydrogen bromide; zinc dibromide In water | 99.1% |
With hydrogenchloride; Zinc chloride In water; toluene | 98.9% |
Trimethylhydroquinone
dimethyl sulfate
1,4-dimethoxy-2,3,5-trimethyl-benzene
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 18h; Ambient temperature; | 99% |
With sodium hydroxide In ethanol; water; ethyl acetate at 0 - 20℃; for 2 - 4h; | 88% |
With potassium carbonate In acetone Heating; | 82% |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium chloride; scandium tris(trifluoromethanesulfonate) In ethyl acetate; toluene | 99% |
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 125 - 145℃; for 3.25h; Product distribution / selectivity; Heating / reflux; | 98.6% |
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 98.1% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 98.1% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 95.9% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 95.9% |
3-Methylbutenoic acid
Trimethylhydroquinone
6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
Conditions | Yield |
---|---|
With methanethiosulfonic acid at 70℃; for 1.5h; | 98% |
With methanesulfonic acid at 70℃; for 4h; | 87% |
With methanesulfonic acid at 85℃; for 3h; | 85% |
Conditions | Yield |
---|---|
aluminum ion-exchanged montmorilonites In octane for 3h; Product distribution; Heating; var. metal ion-exchanged montmorilonites, var. solvents, var. reaction time; | 98% |
Conditions | Yield |
---|---|
With sodium chloride In ethyl acetate; toluene | 98% |
isophytol
Trimethylhydroquinone
A
vitamin E
B
2-phytyl-3,5,6-trimethylhydroquinone
Conditions | Yield |
---|---|
indium (III) iodide In Ethylene carbonate; n-heptane at 140 - 145℃; for 2h; Product distribution / selectivity; Heating / reflux; | A 97.3% B 0.25% |
indium(III) chloride In pentan-3-one at 140 - 145℃; for 5h; Product distribution / selectivity; Heating / reflux; | A 95.1% B 0.37% |
indium(III) chloride In Ethylene carbonate; n-heptane at 140 - 145℃; for 2 - 5h; Product distribution / selectivity; Heating / reflux; | A 94.8% B 0% |
(3RS,7R,11R)-3,7,11,15-tetramethylhexadec-1-en-3-ol
Trimethylhydroquinone
(2RS,4R,8R)-α-tocopherol
Conditions | Yield |
---|---|
With Zeokar 10 aluminosilicate In various solvent(s) for 5h; Heating; | 97% |
With boron trifluoride In diethyl ether |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; xylene at 130 - 135℃; for 4h; | 96% |
Conditions | Yield |
---|---|
gadolinium(III) trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 125 - 130℃; for 2.5h; Product distribution / selectivity; Heating / reflux; | 95% |
Conditions | Yield |
---|---|
Stage #1: Trimethylhydroquinone; trimethyl orthoformate In methanol for 0.0833333h; Inert atmosphere; Stage #2: 4-penten-3-one With sulfuric acid In methanol at 0 - 20℃; for 48h; Inert atmosphere; | 95% |
Trimethylhydroquinone
tert-butylchlorodiphenylsilane
4-[(tert-butyldiphenylsilyl)oxy]-2,3,6-trimethylphenol
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at -30 - 20℃; Inert atmosphere; | 94% |
With 1H-imidazole In tetrahydrofuran for 12h; Ambient temperature; | 90% |
Trimethylhydroquinone
methyl vinyl ketone
trimethyl orthoformate
2,5,7,8-tetramethyl-2-methoxy-6-hydroxychroman
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 20℃; for 48h; | 94% |
With sulfuric acid In methanol at 20℃; for 48h; | 94% |
With sulfuric acid In methanol at 20℃; | 64% |
Stage #1: Trimethylhydroquinone; trimethyl orthoformate In methanol for 0.0833333h; Inert atmosphere; Stage #2: methyl vinyl ketone With sulfuric acid In methanol at 0 - 20℃; for 48h; Inert atmosphere; | 60% |
isophytol
Trimethylhydroquinone
A
vitamin E
B
(all-rac)-3,4-dehydro-α-tocopherol
Conditions | Yield |
---|---|
indium(III) chloride In n-heptane at 147℃; under 2550.26 Torr; for 3.1h; Product distribution / selectivity; | A 93.7% B n/a |
Reported in EPA TSCA Inventory.
Trimethylhydroquinone, its cas register number is 700-13-0. It also can be called 1,4-benzenediol, 2,3,5-trimethyl-; 2,3,5-Trimethyl-1,4-benzenediol; 2,3,5-Trimethylbenzene-1,4-diol; and 2,3,5-Trimethylbenzol-1,4-diol. Its classification code is Reproductive Effect.
Trimethylhydroquinone could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.
Physical properties about Trimethylhydroquinone are: (1)ACD/LogP: 1.675; (2)ACD/LogD (pH 5.5): 1.68; (3)ACD/LogD (pH 7.4): 1.67; (4)ACD/BCF (pH 5.5): 11.03; (5)ACD/BCF (pH 7.4): 11.03; (6)ACD/KOC (pH 5.5): 194.06; (7)ACD/KOC (pH 7.4): 194.02; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.573; (12)Molar Refractivity: 44.491 cm3; (13)Molar Volume: 135.119 cm3; (14)Polarizability: 17.638 10-24cm3; (15)Surface Tension: 45.140998840332 dyne/cm ; (16)Density: 1.126 g/cm3; (17)Flash Point: 146.269 °C; (18)Enthalpy of Vaporization: 55.969 kJ/mol; (19)Boiling Point: 298.253 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable gloves and eye/face protection;
3. This material and/or its container must be disposed of as hazardous waste;
4. Avoid release to the environment. Refer to special instructions safety data sheet;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H12O2/c1-5-4-8(10)6(2)7(3)9(5)11/h4,10-11H,1-3H3;
(2)InChIKey=AUFZRCJENRSRLY-UHFFFAOYSA-N;
(3)Smilesc1(c(c(cc(c1O)C)O)C)C
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 65mg/kg (65mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 125, 1993. |
rabbit | LD50 | skin | > 200mg/kg (200mg/kg) | BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 125, 1993. | |
rat | LC50 | inhalation | 1500mg/m3/4H (1500mg/m3) | CARDIAC: OTHER CHANGES SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE LUNGS, THORAX, OR RESPIRATION: EMPHYSEMA | BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 125, 1993. |
rat | LD50 | oral | 3200mg/kg (3200mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 125, 1993. |
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