Conditions | Yield |
---|---|
With dihydrogen peroxide; Ti-superoxide In water; acetic acid for 1.25h; Product distribution / selectivity; Heating / reflux; | A 0.5% B 99% |
Conditions | Yield |
---|---|
With sodium dithionite In diethyl ether; dichloromethane; water at 20℃; | 98% |
With hydrogen; palladium on activated charcoal In ethyl acetate for 4h; Ambient temperature; | 96% |
With 1,1,3,3-Tetramethyldisiloxane; iodine In dichloromethane for 0.5h; Heating; | 90% |
Conditions | Yield |
---|---|
With cis-bisglycinato copper(II) monohydrate; dihydrogen peroxide at 20℃; Oxidation; | 98% |
With sulfuric acid bei der elektrolytischen Oxydation; | |
With dihydrogen peroxide; acetic acid at 60℃; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity; Heating / reflux; | A 3% B 96% |
With dihydrogen peroxide; copper(II) hydroxide phosphate In cyclohexane; water at 66℃; for 2h; Product distribution / selectivity; | |
With dihydrogen peroxide; copper(II) hydroxide phosphate In n-heptane; water at 73℃; for 2h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; | A 9% B 91% |
1,4-O-di-propanoylmethylhydroquinone
C
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
With isopropyl alcohol; Candida antarctica lipase B; immobilized In di-isopropyl ether at 45℃; for 1h; Title compound not separated from byproducts.; | A 81.6% B 4.5% C 13.9% |
4-(cyclopenten-1-yl)-o-cresol
A
2-methylbenzene-1,4-diol
B
cyclopentanone
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide In acetonitrile at 50℃; for 3h; the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C; | A 70.3% B n/a |
2-Methyl-1,4-benzoquinone
A
2-methylbenzene-1,4-diol
C
bis-(4-chloro-phenyl)-diazene
Conditions | Yield |
---|---|
In tetrahydrofuran 0 deg C, 1 h, RT, 1 h, 55 deg C, 0.5 h; | A 67% B 9% C 6% |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium persulfate at 20℃; for 3h; | 66% |
With dihydrogen peroxide; acetic acid at 20℃; | |
With potassium nitrite; ethanol; acetic acid Erhitzen der Reaktionsloesung mit wss. H3PO4 und anschliessendes Reduzieren mit Na2S2O4; |
A
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
In toluene Heating; | A 20% B 43% |
ortho-cresol
A
2-methylbenzene-1,4-diol
B
2,2'-dimethyl-4,4'-biphenol
C
4,4'-dihydroxy-3,3'-dimethyl-6-nitrobiphenyl
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium dodecyl-sulfate In acetic acid for 48h; Ambient temperature; | A 30% B 20% C 15% |
With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium dodecyl-sulfate In water; acetic acid at 30℃; for 2h; | A 47 % Spectr. B 20 % Spectr. C 15 % Spectr. |
2-Methyl-1,4-benzoquinone
Cyclohepta-1,3,5-triene
A
5,6-Di-cyclohepta-2,4,6-trienyl-2-methyl-cyclohex-2-ene-1,4-dione
B
2-methylbenzene-1,4-diol
C14H14O2
Conditions | Yield |
---|---|
In toluene for 2.5h; Heating; | A 14% B 284 mg C 18% |
ortho-cresol
A
4-methyl resorcinol
B
2-methylbenzene-1,4-diol
C
2-methylbenzene-1,3-diol
D
3-methylbenzene-1,2-diol
Conditions | Yield |
---|---|
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -40℃; for 0.5h; Product distribution; | A 3% B 17% C 3% D 4% |
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -40℃; for 0.5h; | A 3% B 17% C 3% D 4% |
C13H14O2
A
2-methylbenzene-1,4-diol
(3aS,5aR,8aS,8bR)-2-Methyl-3a,4,5,5a,8a,8b-hexahydro-as-indacene-1,8-dione
Conditions | Yield |
---|---|
at 600℃; under 0.8 Torr; flash vacuum pyrolysis; | A n/a B 15% |
Conditions | Yield |
---|---|
at 350℃; under 112509 Torr; for 2h; | 15% |
1,4-O-di-propanoylmethylhydroquinone
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
With Candida antarctica lipase B In di-isopropyl ether; isopropyl alcohol at 45℃; for 1h; Enzymatic reaction; regioselective reaction; | 14% |
Conditions | Yield |
---|---|
A 4% B n/a |
ortho-cresol
A
(4S,5R,6S)-4,5-dihydroxy-6-methylcyclohex-2-en-1-one
B
2-methylbenzene-1,4-diol
D
3-methylbenzene-1,2-diol
Conditions | Yield |
---|---|
With oxygen Enzymatic reaction; | A n/a B n/a C n/a D n/a E 0.56% |
Conditions | Yield |
---|---|
With potassium peroxomonosulphate; sulfuric acid at 70 - 80℃; | |
With potassium peroxomonosulphate Kochen der Loesung mit Saeure; |
Conditions | Yield |
---|---|
With sulfuric acid nachfolgend Destillieren mit Wasserdampf; | |
With sulfuric acid at 50 - 70℃; |
Conditions | Yield |
---|---|
With sulfuric acid bei der elektrolytischen Oxydation; |
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanol Hydrogenolyse; |
Conditions | Yield |
---|---|
With sulfuric acid; aluminium |
4-hydroxy-4-methyl-cyclohexa-2,5-dienone
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate |
Conditions | Yield |
---|---|
With barium dihydroxide; water at 165 - 190℃; in einem Kupferkessel; |
Conditions | Yield |
---|---|
With sulfuric acid |
benzaldehyde
2-Methyl-1,4-benzoquinone
benzene
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
Einwirkung von Sonnenlicht; |
2-Methyl-1,4-benzoquinone
orthoformic acid triethyl ester
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
Einwirkung von Sonnenlicht; |
(E)-3-phenylpropenal
2-Methyl-1,4-benzoquinone
benzene
2-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
Einwirkung von Sonnenlicht; |
diacetyl peroxide
acetic acid
ortho-cresol
A
2-methylbenzene-1,4-diol
B
3-methylbenzene-1,2-diol
Conditions | Yield |
---|---|
anschl. Erwaermen mit methanol. HCl; |
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature; | 100% |
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Mechanism; Ambient temperature; other substrates; | 100% |
With nitric acid; bentonite for 0.05h; Product distribution; Further Variations:; Reagents; reaction times; types of irradiation; Oxidation; Irradiation; | 100% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 12h; | 100% |
With pyridine at 20℃; for 24h; | 100% |
With pyridine at 20℃; for 2h; | 99% |
2-methylbenzene-1,4-diol
ethyl acetoacetate
6-hydroxy-4,7-dimethyl-2H-chromen-2-one
Conditions | Yield |
---|---|
With sulfuric acid at 0℃; for 1h; Pechmann Condensation; Milling; | 100% |
With sulfuric acid Pechmann Condensation; Inert atmosphere; | 77% |
With sulfuric acid | |
With sulfuric acid at 20℃; for 24h; Pechmann condensation; Inert atmosphere; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 24h; | 100% |
With potassium carbonate In butanone for 24h; | 94% |
With potassium hydroxide In methanol for 8h; steam distillation; | 82% |
Conditions | Yield |
---|---|
With potassium hydroxide; Aliquat 336 In 1,2-dimethoxyethane for 24h; Heating; | 100% |
In ethanol Etherification; Heating; |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 25℃; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 20℃; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 0℃; for 0.5h; | 95% |
4-hydroxy[1]benzopyran-2-one
2-methylbenzene-1,4-diol
2,3-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione
Conditions | Yield |
---|---|
With laccase from Trametes versicolor at 20℃; for 20h; pH=4.37; aq. acetate buffer; Enzymatic reaction; regioselective reaction; | 98% |
iodomethane-d3
2-methylbenzene-1,4-diol
1,4-[2H6]dimethoxy-2-methylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide at 55℃; for 96h; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid at 0℃; for 1h; Pechmann Condensation; Milling; | 96% |
2-methylbenzene-1,4-diol
(μ-2-methyl-1,4-benzenediolato(2-))bis[dichloro(pentamethylcyclopentadienyl)titanium(IV)]
Conditions | Yield |
---|---|
In diethyl ether byproducts: methane; under Ar; soln. of methylhydroquinone in Et2O slowly cannulated into soln. of Ti(C5Me5)Cl2Me (2 equiv) in Et2O; mixt. stirred overnight at room temp.; solvent evapd. under vac.; product recrystd. in mixt. Et2O-hexane; | 95% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; Reflux; Inert atmosphere; | 95% |
2-methylbenzene-1,4-diol
3,5,6-tribromotoluquinone
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide In water; acetic acid at 60℃; for 5h; Mechanism; other substrates; | 94% |
With benzyltrimethylammonium tribromide In water; acetic acid at 60℃; for 5h; | 94% |
2-methylbenzene-1,4-diol
tert-butyldimethylsilyl chloride
(2-methyl-1,4-phenylene)bis(oxy)bis(tert-butyldimethylsilane)
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.416667h; Ambient temperature; | 94% |
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 7h; | 93% |
2-methylbenzene-1,4-diol
(S)-2-methylbutyl tosylate
1,4-Bis[(S)-2-methylbutoxy]-2-methylbenzene
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium carbonate In butanone for 16h; Etherification; Williamson etherification; Heating; | 94% |
2-methylbenzene-1,4-diol
2-methyl-1,4-phenylene bis(4-(4-(acryloyloxy)butoxy)-benzoate)
Conditions | Yield |
---|---|
With hydrogenchloride; dmap; diisopropyl-carbodiimide In tetrahydrofuran at 40℃; for 5h; Solvent; | 94% |
Stage #1: 4-[(4-propenoyloxy)butyloxy]benzoic acid With methanesulfonyl chloride; triethylamine In tetrahydrofuran; ethyl acetate for 1h; Cooling with ice; Stage #2: 2-methylbenzene-1,4-diol With triethylamine In tetrahydrofuran; ethyl acetate at 20℃; for 2h; Reagent/catalyst; Cooling with ice; |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 7h; Heating; | 93.9% |
2-methylbenzene-1,4-diol
2-ethylhexyl 4-methylbenzenesulfonate
1,4-bis(2-ethylhexyloxy)-2-methylbenzene
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium carbonate In butanone for 16h; Heating; | 93% |
2-methylbenzene-1,4-diol
4-hydroxy-benzoic acid
2-methyl-1,4-phenylene bis(4-hydroxybenzoate)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In para-xylene for 20h; Dean-Stark; Reflux; | 93% |
With toluene-4-sulfonic acid In ortho-diethylbenzene at 180℃; for 4h; | 85% |
With toluene-4-sulfonic acid In xylenes at 20℃; for 44h; Heating / reflux; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; xylene at 130 - 135℃; for 4h; | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In water at 40℃; for 1h; Solvent; Temperature; Green chemistry; | 92% |
2-methylbenzene-1,4-diol
4-(n-but-3'-enyloxy)benzoic acid
2-methyl-1,4-bis[4-(4-butenyloxy)benzoyl]hydroquinone
Conditions | Yield |
---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; | 90% |
2-methylbenzene-1,4-diol
2-methyl-1,4-phenylene bis(4-(4-(acryloyloxy)butoxy)-benzoate)
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; triethylamine In tetrahydrofuran; ethyl acetate at 23℃; for 3h; | 90% |
2-methylbenzene-1,4-diol
4-fluorobenzhydrol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In water at 40℃; for 1h; Green chemistry; | 90% |
2-methylbenzene-1,4-diol
2,3-dimethyl-buta-1,3-diene
2,6,7-trimethylnaphthalene-1,4-dione
Conditions | Yield |
---|---|
With oxygen; pyrographite In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; under 760.051 Torr; for 36h; Schlenk technique; Cooling with ice; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid for 0.0666667h; Microwave irradiation; | 89% |
With sulfuric acid |
Reported in EPA TSCA Inventory.
2-Methylhydroquinone, with the CAS NO.95-71-6, is also called 2,5-Dihydroxytoluene; THQ; Toluhydroquinone; methyl hydroquinone; 2-Methylhydroquinone; P-toluhydroquinone; 2-Methyl Hydroquinone. It belongs to the Product Categories of Intermediates of Dyes and Pigments; Anthraquinones, Hydroquinones and Quinones; Building Blocks; Chemical Synthesis; Organic Building Blocks; Oxygen Compounds; Polyols. 2-Methylhydroquinone is a tan to white crystalline solid. 2-Methylhydroquinone undergoes chemical reactions similar to those of hydroquinone. The presence of a methyl group in the ortho position in the toluhydroquinone molecule accounts for the slight structural and behavioral differences between toluhydroquinone and hydroquinone. 2-Methylhydroquinone is a highly active inhibitor in the free radical polymerization of vinyl monomers and unsaturated polyesters.
Physical properties about 2-Methylhydroquinone are: (1)ACD/LogP: 1.002; (2)ACD/LogD (pH 5.5): 1.00; (3)ACD/LogD (pH 7.4): 1.00; (4)ACD/BCF (pH 5.5): 3.40; (5)ACD/BCF (pH 7.4): 3.40; (6)ACD/KOC (pH 5.5): 83.59; (7)ACD/KOC (pH 7.4): 83.54; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.595; (12)Molar Refractivity: 34.841 cm3; (13)Molar Volume: 102.568 cm3 ; (14)Polarizability: 13.812 10-24cm3; (15)Surface Tension: 51.632999420166 dyne/cm; (16)Density: 1.21 g/cm3; (17)Flash Point: 140.247 °C; (18)Enthalpy of Vaporization: 53.714 kJ/mol; (19)Boiling Point: 277.798 °C at 760 mmHg; (20)Vapour Pressure: 0.00300000002607703 mmHg at 25°C
Uses of 2-Methylhydroquinone: It can be used as an effective polymerization retarder and inhibitor for acrylonitrile and vinyl monomers, and it is a useful antioxidant for oleate and linseed oil, etc. Also, it is used as a component of photographic developers and an inertmediate of photographic agents.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3;
(2)InChIKey=CNHDIAIOKMXOLK-UHFFFAOYSA-N;
(3)Smilesc1(c(ccc(c1)O)O)C;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | skin | > 1gm/kg (1000mg/kg) | Kodak Company Reports. Vol. 21MAY1971, | |
mouse | LD50 | oral | > 400mg/kg (400mg/kg) | Kodak Company Reports. Vol. 21MAY1971, | |
rat | LDLo | intraperitoneal | 200mg/kg (200mg/kg) | Kodak Company Reports. Vol. 21MAY1971, | |
rat | LDLo | oral | 200mg/kg (200mg/kg) | Kodak Company Reports. Vol. 21MAY1971, |
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