Conditions | Yield |
---|---|
With sodium dithionite In diethyl ether; water | 100% |
With sodium dithionite In diethyl ether; water at 20℃; | 100% |
With isopropyl alcohol; zirconium(IV) oxide for 2h; Heating; | 99% |
Conditions | Yield |
---|---|
With 2-Ethylhexanoic acid; [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)]; dihydrogen peroxide In acetonitrile at 0℃; for 2.5h; | 99% |
Conditions | Yield |
---|---|
With cis-bisglycinato copper(II) monohydrate; dihydrogen peroxide at 70℃; for 4h; Oxidation; | 98% |
With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature; | 56% |
With sodium hydroxide; dipotassium peroxodisulfate Erhitzen des mit wss. HCl angesaeuerten Reaktionsgemisches; |
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; | A 2% B 98% |
2.6-dimethylphenol
A
1,4-dihydroxy-2,6-dimethylbenzene
B
2,6-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity; | A 2% B 97% |
2,6-dimethyl-1,4-benzoquinone
dibenzylamine
A
1,4-dihydroxy-2,6-dimethylbenzene
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 70℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere; | A 6% B 94% |
Conditions | Yield |
---|---|
With dihydrogen peroxide at 20℃; for 1h; Dakin Phenol Oxidation; Green chemistry; | 92% |
With 7,8-difluoro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; dihydrogen peroxide; sodium hydrogencarbonate In methanol; water at 20℃; for 0.333333h; Dakin oxidation; | 91% |
With dihydrogen peroxide In water at 20℃; for 3h; Dakin Phenol Oxidation; Green chemistry; | 88% |
Conditions | Yield |
---|---|
With tetrabutylammonium tricarbonylnitrosylferrate In ethanol at 40℃; for 1h; Michael Addition; Inert atmosphere; Microwave irradiation; | A 10% B 80% |
2,6-dimethyl-cyclohex-3-ene-1,2-diol
A
1,4-dihydroxy-2,6-dimethylbenzene
B
2,6-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h; | A 71% B 6% |
4-hydroxy-3,5-dimethylbenzaldehyde
A
1,4-dihydroxy-2,6-dimethylbenzene
B
2,6-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; oxygen; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 3h; Dakin Phenol Oxidation; | A 23% B 65% |
4-(cyclopenten-1-yl)-2,6-dimethylphenol
A
1,4-dihydroxy-2,6-dimethylbenzene
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 60% B n/a |
1,3-dimethyl-2,5-bis-prop-2-ynyloxy-benzene
A
1,4-dihydroxy-2,6-dimethylbenzene
B
3,5-dimethyl-4-prop-2-ynyloxy-phenol
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at 20℃; for 0.5h; | A 6% B 55% |
2,6-dimethyl-1,4-benzoquinone
A
ditropenyl
B
1,4-dihydroxy-2,6-dimethylbenzene
C
2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone
Conditions | Yield |
---|---|
With Cyclohepta-1,3,5-triene In toluene for 1.5h; Heating; | A 6% B 40 mg C 14% |
2,6-dimethyl-1,4-benzoquinone
Cyclohepta-1,3,5-triene
A
ditropenyl
B
1,4-dihydroxy-2,6-dimethylbenzene
C
2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone
Conditions | Yield |
---|---|
In toluene for 1.5h; Heating; | A 6% B 40 mg C 14% |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With sulfuric acid | |
With hydrogenchloride; sodium dithionite; iron(III) chloride Multistep reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide; dipotassium peroxodisulfate Erhitzen des mit wss. HCl angesaeuerten Reaktionsgemisches; | |
(i) aq. (KO3S)2NO, NaOAc, acetone, (ii) NaBH4, MeOH; Multistep reaction; |
2,6-dimethyl-1,4-benzoquinone
methyllithium
A
1,4-dihydroxy-2,6-dimethylbenzene
Conditions | Yield |
---|---|
ether, THF, -78 deg C; 60 min; Yield given. Multistep reaction. Yields of byproduct given; |
O-(2,6-dimethylphenyl)hydroxylamine
trifluoroacetic anhydride
A
2.6-dimethylphenol
B
1,4-dihydroxy-2,6-dimethylbenzene
Conditions | Yield |
---|---|
With trifluoroacetic acid 1.) CH2Cl2, -20 deg C, 6 h, 2.) CH2Cl2, -20 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid Heating; |
2,6-dimethyl-1,4-benzoquinone
3,5-dimethyl-2-(p-tolylthio)benzene-1,4-diol
A
1,4-dihydroxy-2,6-dimethylbenzene
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 24℃; Equilibrium constant; further compound; | |
With sodium acetate In methanol; water at 24℃; Equilibrium constant; |
2,6-dimethyl-1,4-benzoquinone
3,5-dimethyl-2-(phenylsulfonyl)benzene-1,4-diol
A
1,4-dihydroxy-2,6-dimethylbenzene
B
2,6-dimethyl-3-phenylsulfonyl-1,4-benzoquinone
Conditions | Yield |
---|---|
With sodium acetate In methanol; water at 24℃; Equilibrium constant; |
Conditions | Yield |
---|---|
(i) Zn, aq. H2SO4, (ii) Fe2(SO4)3, (iii) aq. Na2S2O4, benzene; Multistep reaction; |
2,6-dimethyl-1,4-benzosemiquinone anion radical
A
1,4-dihydroxy-2,6-dimethylbenzene
B
2,6-dimethyl-1,4-benzoquinone
Conditions | Yield |
---|---|
In water at 22℃; Rate constant; |
Conditions | Yield |
---|---|
Erwaermen mit wss. HCl; |
Conditions | Yield |
---|---|
Erwaermen der Reaktionsloesung mit wss. HCl; |
2.6-dimethylphenol
sulfuric acid
dihydrogen peroxide
acetic acid
A
1,4-dihydroxy-2,6-dimethylbenzene
B
3,3',5,5'-tetramethyldiphenoquinone
C
3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With nitric acid; sodium nitrite In methanol at -10℃; | 100% |
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 2h; | 91% |
With air; cobalt(II) phthalocyanine; Montmorillonite K10 In 1,4-dioxane; water at 20℃; for 6h; | 90% |
1,4-dihydroxy-2,6-dimethylbenzene
tert-butyldimethylsilyl chloride
2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-benzene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 12h; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride for 17h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With hydrogenchloride for 37h; Ambient temperature; | 92% |
3-pyridinecarboxaldehyde
1,4-dihydroxy-2,6-dimethylbenzene
(3,6-dihydroxy-2,4-dimethylphenyl)-(3-pyridyl)methanol
Conditions | Yield |
---|---|
With hydrogenchloride for 17h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 3h; | 89% |
Conditions | Yield |
---|---|
With sulfuric acid Heating; | 87% |
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid-d2 Heating; | 85% |
1,4-dihydroxy-2,6-dimethylbenzene
methyl iodide
1,3-dimethyl-2,5-dimethoxybenzene
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide | 84% |
With sodium hydride In tetrahydrofuran for 12h; Heating; | 83% |
Stage #1: 1,4-dihydroxy-2,6-dimethylbenzene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 60% |
1,4-dihydroxy-2,6-dimethylbenzene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In chloroform at 20℃; for 1h; | 80% |
2-methyl-3-buten-2-ol
1,4-dihydroxy-2,6-dimethylbenzene
2,2,5,7-tetramethyl-6-chromanol
Conditions | Yield |
---|---|
With hydrogenchloride; silica gel; zinc(II) chloride In tetrachloromethane for 1.33333h; Heating; | 79% |
2-hydroxy-2-methylbut-3-enenitrile
1,4-dihydroxy-2,6-dimethylbenzene
6-hydroxy-2,5,7-trimethyl-2-cyanochromane
Conditions | Yield |
---|---|
With phosphoric acid In nitromethane; boron trifluoride; toluene | 79% |
Conditions | Yield |
---|---|
With Burkholderia cepacia lipase immobilized on Celite In tert-Amyl alcohol; cyclohexane at 45℃; for 72h; | A 78.8% B 3.5% |
Methyl 3,3-dimethylacrylate
1,4-dihydroxy-2,6-dimethylbenzene
6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin
Conditions | Yield |
---|---|
With methanesulfonic acid at 70℃; for 2h; | 76.9% |
With sulfuric acid In benzene | 63% |
With sulfuric acid In benzene for 3h; Heating; | 40% |
With methanesulfonic acid at 70℃; for 1.5h; |
methanol
1,4-dihydroxy-2,6-dimethylbenzene
methyl vinyl ketone
2-Methoxy-2,5,7-trimethyl-chroman-6-ol
Conditions | Yield |
---|---|
With sulfuric acid | 74% |
1,4-dihydroxy-2,6-dimethylbenzene
isobutyraldehyde
2,3-dihydro-5-hydroxy-2,2,4,6-tetramethylbenzofuran
Conditions | Yield |
---|---|
With hydrogenchloride In water; toluene for 12h; Reflux; | 74% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 140℃; | 73% |
1,4-dihydroxy-2,6-dimethylbenzene
propargyl bromide
1,3-dimethyl-2,5-bis-prop-2-ynyloxy-benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 80℃; | 73% |
1,4-dihydroxy-2,6-dimethylbenzene
(E)-6-chloro-3-methyl-2-hexene-1-ol
2-(3-chloropropyl)-2,5,7-trimethyl-6-chromanol
Conditions | Yield |
---|---|
With zinc(II) chloride Heating; | 71% |
With hydrogenchloride; acetic acid; zinc(II) chloride 1.) 90 deg C, 16 h, 2.) MeOH, reflux, 2 h; Yield given. Multistep reaction; |
3-Methylbutenoic acid
1,4-dihydroxy-2,6-dimethylbenzene
6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin
Conditions | Yield |
---|---|
With methanesulfonic acid at 70℃; for 18h; | 67% |
In various solvent(s) at 70℃; | |
With methanesulfonic acid at 70℃; |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-benzoic acid With acetic acid In toluene at 90℃; for 0.25h; Stage #2: 1,4-dihydroxy-2,6-dimethylbenzene In toluene at 110℃; for 6h; | 65.3% |
The 2,6-Dimethylhydroquinone with cas registry number of 654-42-2 is also known as MXHQ; m-Xhq; Metaxylohydroquinone. It belongs to the categories of Industrial/Fine Chemicals; Anthraquinones, Hydroquinones and Quinones. Its EINECS registry number is 211-505-2. It has an IUPAC name which is 2,6-dimethylbenzene-1,4-diol.
Physical properties about this chemical are: (1)ACD/LogP: 1.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.56; (4)ACD/LogD (pH 7.4): 1.56; (5)ACD/BCF (pH 5.5): 9.1; (6)ACD/BCF (pH 7.4): 9.1; (7)ACD/KOC (pH 5.5): 169.07; (8)ACD/KOC (pH 7.4): 169; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2 ; (12)Index of Refraction: 1.582; (13)Molar Refractivity: 39.66 cm3; (14)Molar Volume: 118.8 cm3; (15)Surface Tension: 47.8 dyne/cm; (16)Density: 1.162 g/cm3; (17)Flash Point: 141.1 °C; (18)Enthalpy of Vaporization: 54.46 kJ/mol; (19)Boiling Point: 284.6 °C at 760 mmHg; (20)Vapour Pressure: 0.00172 mmHg at 25°C.
Preparation of 2,6-Dimethylhydroquinone: this chemical can be made by 2,6-dimethyl-phenol using reagents cis-bisglycinato copper (II) monohydrate and H2O2. This reaction is a kind of Oxidation. Its reaction time is 4 hours. And its reaction temperature is 70 ℃. The yield is 98%.
Uses of 2,6-Dimethylhydroquinone: it can react with methanol to give 4-Methoxy-2,6-dimethyl-phenol using reagent conc. H2SO4. The yield is about 87%.
When you are using this chemical, please be cautious about it as the following:
Poison by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by ingestion: impaired spermatogenesis in men and changes in fertility in women. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. Wear suitable protective clothing, gloves and eye/face protection during using it. 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)InChI: InChI=1/C8H10O2/c1-5-3-7(9)4-6(2)8(5)10/h3-4,9-10H,1-2H3;
(2)Smiles: Cc1c(O)c(C)cc(O)c1
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intraperitoneal | 20mg/kg (20mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
mouse | LD50 | intraperitoneal | 117mg/kg (117mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
mouse | LD50 | oral | 186mg/kg (186mg/kg) | Indian Journal of Experimental Biology. Vol. 2, Pg. 23, 1964. |
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