Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature; | 100% |
With oxygen; Nitrogen dioxide In dichloromethane at -10℃; for 12h; | 100% |
With oxygen; Nitrogen dioxide In dichloromethane at -10℃; for 12h; | 100% |
2,3-dibromo-5,6-dimethylcyclohexa-2,5-diene-1,4-dione
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With iron; acetic acid at 20℃; for 6h; Reflux; | 96.3% |
3,6-dimethoxy-o-xylene
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With cerium(IV) ammonium nitrate; silica gel In dichloromethane for 0.25h; | 93% |
With ammonium cerium (IV) nitrate; silica gel In dichloromethane; water | 63% |
With ammonium cerium (IV) nitrate; silica gel In dichloromethane; water | 1.68 g |
Conditions | Yield |
---|---|
With potassiuim nitrosodisulfonate; sodium acetate In water | 75% |
With potassium dihydrogenphosphate; potassium nitrososulfonate In acetone at 20℃; for 0.666667h; | 65% |
With potassium dihydrogenphosphate; K4(ON(SO3)2)2 In water at 5℃; for 1h; | 60% |
2,3-dimethyl-cyclohex-3-ene-1,2-diol
A
2,3-dimethyl-1,4-benzoquinone
B
2,3-dimethyl-1,4-dihydroxybenzene
Conditions | Yield |
---|---|
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h; | A n/a B 67% |
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
In toluene for 24h; retro Diels-Alder reaction; Heating; | 49% |
2-Methyl-1,4-benzoquinone
tert-butyl alcohol
A
2,3-dimethyl-1,4-benzoquinone
B
2,3,5-Trimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; bis-[(trifluoroacetoxy)iodo]benzene at 120℃; for 5h; Sealed tube; Green chemistry; | A 16% B 42% |
2,3-dimethyl-N-(phenylsulfonyl)aniline
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetic acid for 24h; Ambient temperature; | 41% |
C15H16O2
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
In toluene for 28h; retro Diels-Alder reaction; Heating; | 35% |
2,3-Dimethylphenol
lead(IV) tetraacetate
acetic acid
A
2,3-dimethyl-1,4-benzoquinone
B
(RS)-6-Acetoxy-5,6-dimethyl-2,4-cyclohexadien-1-on
C
6,6-diacetoxy-2,3-dimethyl-cyclohexa-2,4-dienone
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid at 5 - 10℃; | |
With chromium(III) oxide; sulfuric acid | |
With potassium dichromate; sulfuric acid |
Conditions | Yield |
---|---|
With dihydrogen peroxide; Hexafluoroacetone In 1,2-dichloro-ethane at 70℃; for 4h; Yield given; |
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; sodium perchlorate In pyridine; acetonitrile Ambient temperature; electrochemical oxidation, 1.5 F/mol; |
2,3-Dimethylphenol
A
2,3-dimethyl-1,4-benzoquinone
B
2,3-dimethyl-6-nitrophenol
C
5,6-dimethyl-6-nitrocyclohexa-2,4-dienone
D
2,3-dimethyl-4-nitrocyclohexa-2,5-dienone
Conditions | Yield |
---|---|
With Nitrogen dioxide In chloroform-d1 at -60℃; Further byproducts given; | A 13 % Spectr. B 18 % Spectr. C 22 % Spectr. D 31 % Spectr. |
2,3-Dimethylphenol
A
2,3-dimethyl-1,4-benzoquinone
B
3,4-dimethyl-1,2-benzoquinone
Conditions | Yield |
---|---|
With {Ru(IV)(2,2'-bipyridine)2(pyridine)O}(2+) In [D3]acetonitrile at 25℃; Mechanism; Product distribution; | A 89 % Spectr. B 11 % Spectr. |
Conditions | Yield |
---|---|
With iron(III) chloride Yield given; |
2,3-dimethyl-5-phenylsulfonyl-1,4-benzoquinone
2,3-dimethyl-1,4-dihydroxybenzene
A
2,3-dimethyl-1,4-benzoquinone
B
2,3-dimethyl-5-phenylsulfonylhydroquinone
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-dimethyl-1,4-dihydroxybenzene
2,3-dimethyl-5-(4-methylphenylthio)cyclohexa-2,5-diene-1,4-dione
A
2,3-dimethyl-1,4-benzoquinone
B
2,3-Dimethyl-6-p-tolylthiohydrochinon
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 24℃; Equilibrium constant; |
2,3-dimethyl-1,4-benzoquinone radical anion
A
2,3-dimethyl-1,4-benzoquinone
B
2,3-dimethyl-1,4-dihydroxybenzene
Conditions | Yield |
---|---|
In water at 22℃; Rate constant; |
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With water; iron(III) chloride | |
With sulfuric acid; sodium nitrite anschliessend Erwaermen; | |
With sodium dichromate; sulfuric acid |
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With 4-sulfo-benzenediazonium-(1)-betaine at 0℃; anschliessendes Behandeln mit Na2S2O4 und Erhitzen des erhaltenen 4-Amino-2.3-dimethyl-phenols mit wss. H2SO4 und MnO2 (oder Fe2 (SO4)(3) unter Durchleiten von Wasserdampf; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / toluene / 4 h / Heating 2: 71 percent / tetrahydrofuran; diethyl ether 3: PCC; SiO2 / CH2Cl2 / 1 h / 20 °C View Scheme |
2-Methyl-6-acetoxy-cyclohexen-(2)-on
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 71 percent / tetrahydrofuran; diethyl ether 2: PCC; SiO2 / CH2Cl2 / 1 h / 20 °C View Scheme |
p-(2,3-dimethyl-4-hydroxyphenylazo)benzenesulphonic acid
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium dithionite 2: aq. ferric chloride View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid | 13.0 g (95%) |
diethylenetriamine-N,N,N',N",N"-pentaacetic acid pentasodium salt
2,3-dimethyl-1,4-dihydroxybenzene
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide In dichloromethane; acetic acid | 11.8 g (87%) |
Conditions | Yield |
---|---|
In toluene for 28h; Reflux; |
alizarin red S
A
2,3-dimethyl-1,4-benzoquinone
E
sulfur trioxide
F
benzene-1,2-dicarboxylic acid
G
crotonaldehyde
Conditions | Yield |
---|---|
With chromium oxide; water for 0.333333h; pH=7; Catalytic behavior; Reagent/catalyst; UV-irradiation; |
2,3-dimethyl-1,4-benzoquinone
2-(triisopropylsiloxy)-1,3-butadiene
Conditions | Yield |
---|---|
(S)-oxazaborolidine-aluminum bromide at -78℃; for 1h; Diels-Alder reaction; | 99% |
With triflimide activated chiral oxazaborolidine In dichloromethane at -95℃; for 2h; | 98% |
With oxazaborolidinium(1+)*Tf2N(1-) In dichloromethane at -95℃; for 2h; Diels-Alder reaction; | 98% |
With chiral oxazaborolidinium triflimide catalyst In dichloromethane at -95℃; for 2h; Diels-Alder reaction; | 98% |
3,4-diphenyl-2H-isoquinolin-1-one
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper(II) acetate monohydrate In toluene at 120℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; | 99% |
2,3-dimethyl-1,4-benzoquinone
methyllithium
A
4-Hydroxy-2,3,4-trimethyl-cyclohexa-2,5-dienone
C
2,3-dimethyl-1,4-dihydroxybenzene
Conditions | Yield |
---|---|
In diethyl ether at -78℃; for 1h; | A 96% B n/a C 2% |
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; | A 96% B 4% |
2,3-dimethyl-1,4-benzoquinone
trimethyl(2-methylenebut-3-enyl)silane
Conditions | Yield |
---|---|
With triflimide activated chiral oxazaborolidine In toluene at -78℃; for 5h; | 96% |
methanol
2,3-dimethyl-1,4-benzoquinone
2-chloro-5,6-dimethyl-4-methoxyphenol
Conditions | Yield |
---|---|
Stage #1: methanol With acetyl chloride at 0℃; for 0.5h; Stage #2: 2,3-dimethyl-1,4-benzoquinone at 20℃; | 96% |
bis(ethylene)(tricyclohexylphosphine)platinum
2,3-dimethyl-1,4-benzoquinone
ethylene(5-6-η-2,3-dimethylbenzo-1,4-quinone)(tricyclohexylphosphine)platinum
Conditions | Yield |
---|---|
In diethyl ether carried out under dry nitrogen atm., stirring of mixture for 30 min, at room temp.; ppt. removed from mother-liquor, washed with light petroleum, addn. of washings to mother-liquor, soln. reduced in volume giving additional solid, combined crystals washed with light petroleum, elem. anal.; | 95% |
2,3-dimethyl-1,4-benzoquinone
1-benzyl-3-vinyl-1H-indole
Conditions | Yield |
---|---|
With C100H112MgO8P2 In methyl cyclohexane at -25℃; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; enantioselective reaction; | 95% |
2,3-dimethyl-1,4-benzoquinone
dimethyl 2,2-di(prop-2-ynyl)malonate
Conditions | Yield |
---|---|
With [RhCl(cis-cyclooctene)2]2; 4,4',4''-phosphanetriyltribenzonitrile In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; | 91% |
With chlorobis(cyclooctene)rhodium(I) dimer; 4,4',4''-phosphanetriyltribenzonitrile In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; | 91% |
2,3-dimethyl-1,4-benzoquinone
(3-methyl-2-butenyl)trifluorosilane
2,3-dimethyl-5-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione
Conditions | Yield |
---|---|
With iron(III) chloride In formamide at 40℃; for 23h; | 90% |
2,3-dimethyl-1,4-benzoquinone
allyl-trimethyl-silane
6-allyl-2,3-dimethylbenzene-1,4-diol
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; | 90% |
bis(cycloocta-1,5-diene)platinum(0)
2,3-dimethyl-1,4-benzoquinone
{Pt(C6H2(CH3)2O2)(C8H12)}
Conditions | Yield |
---|---|
In diethyl ether mixing under dry nitrogen atm. between -30 and -50°C; ppt. washing with light petroleum at -30°C, dried in vac.; | 90% |
2,3-dimethyl-1,4-benzoquinone
acetic anhydride
1,2,5-triacetoxy-3,4-dimethyl-benzene
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.916667h; Thiele-Winter acetoxylation; | 85% |
With boron trifluoride diethyl etherate for 3h; Ambient temperature; | 77% |
With boron trifluoride diethyl etherate | |
With sulfuric acid | |
With boron trifluoride diethyl etherate |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In 1,2-dichloro-ethane at 90℃; for 16h; | 85% |
2,3-dimethyl-1,4-benzoquinone
1,5-dimethyl-4-amino-1,2,4-triazolium-3-thiolate
toluene-4-sulfonic acid
Toluene-4-sulfonate4-amino-3-(2,5-dihydroxy-3,4-dimethyl-phenylsulfanyl)-1,5-dimethyl-4H-[1,2,4]triazol-1-ium;
Conditions | Yield |
---|---|
In methanol for 24h; Ambient temperature; | 84% |
2,3-dimethyl-1,4-benzoquinone
2,3-dimethyl-buta-1,3-diene
2,3,6,7-tetramethyl-4a,5,8,8a-tetrahydro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With acetic acid at 25 - 27℃; for 24h; | 84% |
In benzene for 4h; Heating; | 80% |
With acetic acid | |
In ethanol Addition; Diels-Alder; Heating; |
1-methylspiro<2,4>-4,6-heptadiene
2,3-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide In water at 20℃; for 5h; Diels-Alder reaction; | 84% |
2,3-dimethyl-1,4-benzoquinone
1,2-diamino-benzene
3,4-dimethylphenazin-2-ol
Conditions | Yield |
---|---|
With acetic acid at -10℃; for 1h; | 84% |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In 1,2-dichloro-ethane at 90℃; for 16h; | 84% |
2,3-dimethyl-1,4-benzoquinone
isoprene
2,3,6-trimethyl-4a,5,8,8a-tetrahydro-1,4-naphthoquinone
Conditions | Yield |
---|---|
In benzene for 4h; Heating; | 83% |
In ethanol Addition; Diels-Alder; Heating; | |
In ethanol at 80℃; for 3h; Diels-Alder reaction; |
2,3-dimethyl-1,4-benzoquinone
para-thiocresol
2,3-dimethyl-5-(4-methylphenylthio)cyclohexa-2,5-diene-1,4-dione
Conditions | Yield |
---|---|
palladium diacetate In tetrahydrofuran at 20℃; for 4h; | 83% |
methanol
2,3-dimethyl-1,4-benzoquinone
5-methoxy-2,3-dimethylcyclohexa-2,5-diene-1,4-dione
Conditions | Yield |
---|---|
With oxygen; cobalt(II) acetate at 60℃; for 47h; Darkness; | 82% |
(i) Ac2O, H2SO4, (ii) /BRN= 1098229/, (iii) AgNO3; Multistep reaction; |
Conditions | Yield |
---|---|
With (S)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst In dichloromethane; acetonitrile at -78 - 23℃; for 7h; | 82% |
meso-diethyl 2,7-diacetamido-4,5-dimethylenoctane-1,8-dioate
2,3-dimethyl-1,4-benzoquinone
meso-diethyl 3,3'-(6,7-dimethyl-5,8-dioxo-5,8-dihydronaphthalene-2,3-diyl)bis(2-acetamidopropanoate)
Conditions | Yield |
---|---|
Stage #1: meso-diethyl 2,7-diacetamido-4,5-dimethylenoctane-1,8-dioate; 2,3-dimethyl-1,4-benzoquinone In toluene at 110℃; for 48h; Diels-Alder reaction; Stage #2: With manganese(IV) oxide In 1,4-dioxane at 20℃; for 48h; Further stages.; | 82% |
Conditions | Yield |
---|---|
With chloranil; acetic acid at 125℃; for 16h; | 82% |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In 1,2-dichloro-ethane at 90℃; for 16h; | 82% |
2,3-dimethyl-1,4-benzoquinone
(E)-cinnamyl(tributyl)tin
5-(trans-cinnamyl)-2,3-dimethylhydroquinone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; | 81% |
The 2,5-Cyclohexadiene-1,4-dione,2,3-dimethyl-, with the CAS registry number 526-86-3, is also known as 2,3-Dimethyl-1,4-benzoquinone. This chemical's molecular formula is C8H8O2 and molecular weight is 136.15. What's more, its systematic name is 2,3-dimethylcyclohexa-2,5-diene-1,4-dione. Its classification code is Mutation data.
Physical properties of 2,5-Cyclohexadiene-1,4-dione,2,3-dimethyl- are: (1)ACD/LogP: 1.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.45; (4)ACD/LogD (pH 7.4): 1.45; (5)ACD/BCF (pH 5.5): 7.39; (6)ACD/BCF (pH 7.4): 7.39; (7)ACD/KOC (pH 5.5): 145.72; (8)ACD/KOC (pH 7.4): 145.72; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.51; (14)Molar Refractivity: 36.54 cm3; (15)Molar Volume: 122 cm3; (16)Polarizability: 14.48×10-24cm3; (17)Surface Tension: 36 dyne/cm; (18)Density: 1.115 g/cm3; (19)Flash Point: 70.9 °C; (20)Enthalpy of Vaporization: 43.65 kJ/mol; (21)Boiling Point: 200.3 °C at 760 mmHg; (22)Vapour Pressure: 0.326 mmHg at 25°C.
Preparation of 2,5-Cyclohexadiene-1,4-dione,2,3-dimethyl-: this chemical can be prepared by 2,3-dimethyl-phenol. This reaction will need reagents hydrated salcomine, O2 and solvent dimethylformamide with the reaction time of 24 hours. The yield is about 33%.
Uses of 2,5-Cyclohexadiene-1,4-dione,2,3-dimethyl-: it can be used to produce 2,3-dibromo-5,6-dimethyl-[1,4]benzoquinone at the ambient temperature. It will need reagent bromine and solvent CHCl3 with the reaction time of 40 hours. The yield is about 66%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=C(C(=O)C=CC1=O)C
(2)InChI: InChI=1S/C8H8O2/c1-5-6(2)8(10)4-3-7(5)9/h3-4H,1-2H3
(3)InChIKey: AIACLXROWHONEE-UHFFFAOYSA-N
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