95-71-6

Basic information

• Product Name: 2-Methylhydroquinone
• Synonyms: METHYLHYDROQUINONE;3-METHYL-1,4-DIHYDROXYBENZENE;2-METHYLHYDROQUINONE;2-METHYL-1,4-BENZENEDIOL;2,5-DIHYDROXYTOLUENE;P-TOLUHYDROQUINOL;P-TOLUHYDROQUINONE;TOLUHYDROQUINONE
• CAS NO: 95-71-6
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• EINECS: 202-443-7
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 95-71-6.mol
• Article Data: 68

Chemical Properties

• Melting Point: 128-130 °C(lit.)
• Boiling Point: 285°C
• Flash Point: 172 °C
• Appearance: Grayish-white to light beige/Crystalline Powder
• Density: 1.1006 (rough estimate)
• Vapor Pressure: 0.00262mmHg at 25°C
• Refractive Index: 1.4922 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 77g/l
• PKA: pK1:10.03;pK2:11.62 (25°C)
• Water Solubility: 77 g/L (25 ºC)
• Stability: Stable. Combustible. Incompatible with oxidizing agents, strong bases.
• BRN: 2041489
• CAS DataBase Reference: 2-Methylhydroquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylhydroquinone(95-71-6)
• EPA Substance Registry System: 2-Methylhydroquinone(95-71-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 2
• RTECS: MX6700000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 95-71-6(Hazardous Substances Data)

Usage

Chemical Properties

white solid

Uses

Different sources of media describe the Uses of 95-71-6 differently. You can refer to the following data:
1. Antioxidant, polymerization inhibitor.
2. Methylhydroquinone is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization.
3. Methylhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway. Allows for screening of novel inhibitors of angiogenesis.

Definition

ChEBI: A member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group.

Synthesis Reference(s)

Tetrahedron, 44, p. 1227, 1988 DOI: 10.1016/S0040-4020(01)85902-0Tetrahedron Letters, 22, p. 2337, 1981 DOI: 10.1016/S0040-4039(01)82900-2

General Description

Methylhydroquinone is produced by the oxidation of o-cresol by the mutants G103S, G103S/A107G, and G103S/A107T.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Methylhydroquinone (Toluquinol) inhibits the growth of endothelial and tumor cells in culture in the micromolar range and is a promising drug candidate in the treatment of cancer and other angiogenesis-related pathologies.

Purification Methods

Crystallise the quinone from EtOH. [Beilstein 6 IV 5866.]

InChI:InChI=1/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3

Synthetic route

3-methyl-phenol (108-39-4) → 2-methylbenzene-1,4-diol (95-71-6) + 2-Methyl-1,4-benzoquinone (553-97-9)

Conditions	Yield
With dihydrogen peroxide; Ti-superoxide In water; acetic acid for 1.25h; Product distribution / selectivity; Heating / reflux;	A 0.5% B 99%

2-Methyl-1,4-benzoquinone (553-97-9) → 2-methylbenzene-1,4-diol (95-71-6)

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%

ortho-cresol (95-48-7) → 2-methylbenzene-1,4-diol (95-71-6)

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℃;

ortho-cresol (95-48-7) → 2-methylbenzene-1,4-diol (95-71-6) + 2-Methyl-1,4-benzoquinone (553-97-9)

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;

2-Methyl-1,4-benzoquinone (553-97-9) → 2-methylbenzene-1,4-diol (95-71-6) + 1,2,4-Trimethyl-cyclohexa-2,5-diene-1,4-diol

Conditions	Yield
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h;	A 9% B 91%

1,4-O-di-propanoylmethylhydroquinone (133411-19-5) → 1-O-propanoyl-2-methylhydroquinone + 4-O-propanoyl-2-methylhydroquinone + 2-methylbenzene-1,4-diol (95-71-6)

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 (78877-82-4) → 2-methylbenzene-1,4-diol (95-71-6) + cyclopentanone (120-92-3)

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 (553-97-9) + /PBCEG004--930/ → 2-methylbenzene-1,4-diol (95-71-6) + 2-(4-Chloro-phenylamino)-3-methyl-[1,4]benzoquinone + bis-(4-chloro-phenyl)-diazene (1602-00-2)

Conditions	Yield
In tetrahydrofuran 0 deg C, 1 h, RT, 1 h, 55 deg C, 0.5 h;	A 67% B 9% C 6%

3-methyl-phenol (108-39-4) → 2-methylbenzene-1,4-diol (95-71-6)

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;

(1-Methyl-2,5-dioxo-cyclopentyl)-acetic acid 4-methyl-2-thioxo-thiazol-3-yl ester → 2-methylbenzene-1,4-diol (95-71-6) + 2-Methyl-2-(4-methyl-thiazol-2-ylsulfanylmethyl)-cyclopentane-1,3-dione

Conditions	Yield
In toluene Heating;	A 20% B 43%

ortho-cresol (95-48-7) → 2-methylbenzene-1,4-diol (95-71-6) + 2,2'-dimethyl-4,4'-biphenol (612-84-0) + 4,4'-dihydroxy-3,3'-dimethyl-6-nitrobiphenyl (112036-06-3)

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 (553-97-9) + Cyclohepta-1,3,5-triene (544-25-2) → 5,6-Di-cyclohepta-2,4,6-trienyl-2-methyl-cyclohex-2-ene-1,4-dione (60457-31-0) + 2-methylbenzene-1,4-diol (95-71-6) + C14H14O2 (60457-29-6, 101759-12-0)

Conditions	Yield
In toluene for 2.5h; Heating;	A 14% B 284 mg C 18%

ortho-cresol (95-48-7) → 4-methyl resorcinol (496-73-1) + 2-methylbenzene-1,4-diol (95-71-6) + 2-methylbenzene-1,3-diol (608-25-3) + 3-methylbenzene-1,2-diol (488-17-5)

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 (112141-86-3) → 2-methylbenzene-1,4-diol (95-71-6) + (3aS,5aR,8aS,8bR)-2-Methyl-3a,4,5,5a,8a,8b-hexahydro-as-indacene-1,8-dione (112141-87-4)

Conditions	Yield
at 600℃; under 0.8 Torr; flash vacuum pyrolysis;	A n/a B 15%

methanol (67-56-1) + hydroquinone (123-31-9) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
at 350℃; under 112509 Torr; for 2h;	15%

1,4-O-di-propanoylmethylhydroquinone (133411-19-5) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With Candida antarctica lipase B In di-isopropyl ether; isopropyl alcohol at 45℃; for 1h; Enzymatic reaction; regioselective reaction;	14%

ortho-cresol (95-48-7) → 2-methylbenzene-1,4-diol (95-71-6) + 3-methylbenzene-1,2-diol (488-17-5)

Conditions	Yield
	A 4% B n/a

ortho-cresol (95-48-7) → (4S,5R,6S)-4,5-dihydroxy-6-methylcyclohex-2-en-1-one (1176877-20-5) + 2-methylbenzene-1,4-diol (95-71-6) + (2S,3R,4S)-3,4-dihydroxy-2-methylcyclohexanone + 3-methylbenzene-1,2-diol (488-17-5) + (4S)-4-hydroxy-2-methylcyclohex-2-en-1-one

Conditions	Yield
With oxygen Enzymatic reaction;	A n/a B n/a C n/a D n/a E 0.56%

p-cresol (106-44-5) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With potassium peroxomonosulphate; sulfuric acid at 70 - 80℃;
With potassium peroxomonosulphate Kochen der Loesung mit Saeure;

p-methylazidobenzene (2101-86-2) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With sulfuric acid nachfolgend Destillieren mit Wasserdampf;
With sulfuric acid at 50 - 70℃;

2-methylmethoxybenzene (578-58-5) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With sulfuric acid bei der elektrolytischen Oxydation;

gentisyl alcohol (495-08-9) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenolyse;

1-methyl-4-nitrobenzene (99-99-0) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With sulfuric acid; aluminium

4-hydroxy-4-methyl-cyclohexa-2,5-dienone (23438-23-5) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With boron trifluoride diethyl etherate

4-Bromo-2-methylphenol (2362-12-1) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With barium dihydroxide; water at 165 - 190℃; in einem Kupferkessel;

N-(4-methylphenyl)hydroxylamine (623-10-9) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
With sulfuric acid

benzaldehyde (100-52-7) + 2-Methyl-1,4-benzoquinone (553-97-9) + benzene (71-43-2) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
Einwirkung von Sonnenlicht;

2-Methyl-1,4-benzoquinone (553-97-9) + orthoformic acid triethyl ester (122-51-0) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
Einwirkung von Sonnenlicht;

(E)-3-phenylpropenal (14371-10-9) + 2-Methyl-1,4-benzoquinone (553-97-9) + benzene (71-43-2) → 2-methylbenzene-1,4-diol (95-71-6)

Conditions	Yield
Einwirkung von Sonnenlicht;

diacetyl peroxide (110-22-5) + acetic acid (64-19-7) + ortho-cresol (95-48-7) → 2-methylbenzene-1,4-diol (95-71-6) + 3-methylbenzene-1,2-diol (488-17-5)

Conditions	Yield
anschl. Erwaermen mit methanol. HCl;

2-methylbenzene-1,4-diol (95-71-6) → 2-Methyl-1,4-benzoquinone (553-97-9)

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%

2-methylbenzene-1,4-diol (95-71-6) + acetic anhydride (108-24-7) → 2,5-diacetoxytoluene (717-27-1)

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 (95-71-6) + ethyl acetoacetate (141-97-9) → 6-hydroxy-4,7-dimethyl-2H-chromen-2-one (5248-20-4)

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;

2-methylbenzene-1,4-diol (95-71-6) + dimethyl sulfate (77-78-1) → 2,5-dimethoxy toluene (24599-58-4)

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%

1-bromo-hexane (111-25-1) + 2-methylbenzene-1,4-diol (95-71-6) → 1,4-Dihexyloxy-2-methylbenzol (157202-49-8)

Conditions	Yield
With potassium hydroxide; Aliquat 336 In 1,2-dimethoxyethane for 24h; Heating;	100%
In ethanol Etherification; Heating;

2-methylbenzene-1,4-diol (95-71-6) + acetyl chloride (75-36-5) → 2,5-diacetoxytoluene (717-27-1)

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 (1076-38-6) + 2-methylbenzene-1,4-diol (95-71-6) → 2,3-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione (1351158-81-0)

Conditions	Yield
With laccase from Trametes versicolor at 20℃; for 20h; pH=4.37; aq. acetate buffer; Enzymatic reaction; regioselective reaction;	98%

iodomethane-d3 (865-50-9) + 2-methylbenzene-1,4-diol (95-71-6) → 1,4-[2H6]dimethoxy-2-methylbenzene (58262-06-9)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide at 55℃; for 96h;	96%

2-methylbenzene-1,4-diol (95-71-6) + ethyl 2-chloro-3-oxo-butyrate (609-15-4) → 3-chloro-6-hydroxy-4,7-dimethyl-2H-chromen-2-one

Conditions	Yield
With sulfuric acid at 0℃; for 1h; Pechmann Condensation; Milling;	96%

dichloro(methyl)(pentamethylcyclopentadienyl)titanium(IV) + 2-methylbenzene-1,4-diol (95-71-6) → (μ-2-methyl-1,4-benzenediolato(2-))bis[dichloro(pentamethylcyclopentadienyl)titanium(IV)] (259255-96-4)

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%

p-(chloromethyl)benzoyl chloride (876-08-4) + 2-methylbenzene-1,4-diol (95-71-6) → C23H18Cl2O4

Conditions	Yield
With triethylamine In dichloromethane for 1h; Reflux; Inert atmosphere;	95%

2-methylbenzene-1,4-diol (95-71-6) → 3,5,6-tribromotoluquinone (29666-53-3)

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 (95-71-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (2-methyl-1,4-phenylene)bis(oxy)bis(tert-butyldimethylsilane) (78018-56-1)

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 (95-71-6) + (S)-2-methylbutyl tosylate (38261-81-3) → 1,4-Bis[(S)-2-methylbutoxy]-2-methylbenzene (312702-75-3)

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium carbonate In butanone for 16h; Etherification; Williamson etherification; Heating;	94%

4-[(4-propenoyloxy)butyloxy]benzoic acid + 2-methylbenzene-1,4-diol (95-71-6) → 2-methyl-1,4-phenylene bis(4-(4-(acryloyloxy)butoxy)-benzoate) (132900-75-5)

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;

2-methylbenzene-1,4-diol (95-71-6) + dimethyl sulfoxide (67-68-5) → 2,5-dimethoxy toluene (24599-58-4)

Conditions	Yield
With sodium hydroxide In ethanol for 7h; Heating;	93.9%

2-methylbenzene-1,4-diol (95-71-6) + 2-ethylhexyl 4-methylbenzenesulfonate (78016-72-5) → 1,4-bis(2-ethylhexyloxy)-2-methylbenzene (354123-99-2)

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium carbonate In butanone for 16h; Heating;	93%

2-methylbenzene-1,4-diol (95-71-6) + 4-hydroxy-benzoic acid (99-96-7) → 2-methyl-1,4-phenylene bis(4-hydroxybenzoate) (119959-84-1)

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;

2-methylbenzene-1,4-diol (95-71-6) + 4-Fluoronitrobenzene (350-46-9) → 2-Methyl-1,4-bis(4'-nitrophenoxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; xylene at 130 - 135℃; for 4h;	92%

4,4'-dimethylbenzhydrol (885-77-8) + 2-methylbenzene-1,4-diol (95-71-6) → 2-(di-p-tolylmethyl)-5-methylbenzene-1,4-diol

Conditions	Yield
With toluene-4-sulfonic acid In water at 40℃; for 1h; Solvent; Temperature; Green chemistry;	92%

2-methylbenzene-1,4-diol (95-71-6) + 4-(n-but-3'-enyloxy)benzoic acid (115595-27-2) → 2-methyl-1,4-bis[4-(4-butenyloxy)benzoyl]hydroquinone (188639-00-1)

Conditions	Yield
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h;	90%

2-methylbenzene-1,4-diol (95-71-6) + 4-(4-acryloyloxybutoxy)benzoic acid chloride → 2-methyl-1,4-phenylene bis(4-(4-(acryloyloxy)butoxy)-benzoate) (132900-75-5)

Conditions	Yield
With 1-methyl-1H-imidazole; triethylamine In tetrahydrofuran; ethyl acetate at 23℃; for 3h;	90%

2-methylbenzene-1,4-diol (95-71-6) + 4-fluorobenzhydrol (149099-27-4, 149243-88-9, 365-22-0) → 2-((4-fluorophenyl)(phenyl)methyl)-5-methylbenzene-1,4-diol

Conditions	Yield
With toluene-4-sulfonic acid In water at 40℃; for 1h; Green chemistry;	90%

2-methylbenzene-1,4-diol (95-71-6) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 2,6,7-trimethylnaphthalene-1,4-dione (59832-90-5)

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%

malic acid (617-48-1) + 2-methylbenzene-1,4-diol (95-71-6) → 6-hydroxy-7-methyl-2H-chromen-2-one (75786-73-1)

Conditions	Yield
With sulfuric acid for 0.0666667h; Microwave irradiation;	89%
With sulfuric acid

Upstream product

• 106-44-5 p-cresol 
• 495-08-9 gentisyl alcohol 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-39-4 3-methyl-phenol 
• 95-48-7 ortho-cresol 
• 74993-52-5 O-(3-methylphenyl)hydroxylamine 
• 78877-82-4 4-(cyclopenten-1-yl)-o-cresol 
• 108-88-3 toluene 
• 30771-65-4 3-Methyl-6-p-tolylthiohydrochinon 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 30771-71-2 2-methyl-6-(phenylsulfonyl)benzene-1,4-diol 
• 100-52-7 benzaldehyde 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 

Downstream Products

• 14554-09-7 5,8-dihydroxy-2-methyl-[1,4]naphthoquinone 
• 5307-05-1 1-hydroxy-4-methoxy-2-methylbenzene 
• 24599-58-4 2,5-dimethoxy toluene 
• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 5140-03-4 2-[4-(2-hydroxyethyl)phenyl]ethan-1-ol 
• 21182-64-9 1-(2,5-dihydroxy-4-methyl-phenyl)-hexadecan-1-one 
• 68825-68-3 4-Hydroxy-2-methyl-phenoxyl 
• 100883-79-2 4-benzoyloxy-2-methyl-cyclohexanone 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 102242-36-4 methylhydroquinone dibenzoate 
• 71528-84-2 4-hydroxy-3-methylphenyl benzoate 
• 2444-25-9 4-Benzoyloxy-3-methyl-phenol 
• 41901-72-8 1,4-diethoxy-2-methyl-5-nitrobenzene 
• 84822-50-4 4-ethoxy-2-methyl-phenol 

Relevant articles and documents

A chemical oscillator based on the photoreduction of 2-methyl-1,4- benzoquinone

This study investigated bromate-2-methyl-1,4-benzoquinone photoreaction in a batch reactor, in which the photoreduction of 2-methyl-1,4-benzoquinone plays a vital role in initiating and sustaining the reaction process. Transient oscillatory phenomena are observed over broad reaction conditions, but a phase diagram in the bromate and sulfuric acid concentration plane shows that the nonlinear behavior is more sensitive to the ratio of bromate and acid than their absolute concentrations. Light intensity and the photosensitive substance 2-methyl-1,4-benzoquinone exhibited opposite effects on the induction time of these oscillations, implying that illumination does more than just reduce 2-methyl-benzoquinone. The oscillatory behavior has been qualitatively reproduced with a generic model developed for bromate-aromatic compounds systems.

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

METHOD AND AGENT FOR TRANSPORTING HYDROGEN

To provide techniques for transporting hydrogen in which problems of energy loss and biological safety are mitigated.SOLUTION: Provided is an agent which is used when transporting hydrogen from location A to location B. This agent is a compound represented by general formula [I] in the figure.SELECTED DRAWING: Figure 1