Product Name

  • Name

    2,6-DIMETHYLHYDROQUINONE

  • EINECS 211-505-2
  • CAS No. 654-42-2
  • Article Data83
  • CAS DataBase
  • Density 1.162 g/cm3
  • Solubility
  • Melting Point 154°C
  • Formula C8H10O2
  • Boiling Point 284.6 °C at 760 mmHg
  • Molecular Weight 138.166
  • Flash Point 141.1 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 654-42-2 (2,6-DIMETHYLHYDROQUINONE)
  • Hazard Symbols Xi,T
  • Synonyms Hydroquinone,2,6-dimethyl- (7CI,8CI);1,4-Dihydroxy-2,6-dimethylbenzene;2,6-Dimethyl-1,4-benzenediol;2,6-Dimethyl-1,4-hydroquinone;2,6-Dimethyl-p-benzohydroquinone;2,6-Dimethylhydroquinone;2,6-Xylohydroquinone;2,6-Xyloquinol;3,5-Dimethylhydroquinone;NSC 36868;m-XHQ;m-Xylene-2,5-diol;m-Xylohydroquinone;
  • PSA 40.46000
  • LogP 1.71460

Synthetic route

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
With sodium dithionite In diethyl ether; water100%
With sodium dithionite In diethyl ether; water at 20℃;100%
With isopropyl alcohol; zirconium(IV) oxide for 2h; Heating;99%
m-xylene
108-38-3

m-xylene

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
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%
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
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;
2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

1,2,4,6-Tetramethyl-cyclohexa-2,5-diene-1,4-diol

1,2,4,6-Tetramethyl-cyclohexa-2,5-diene-1,4-diol

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h;A 2%
B 98%
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

Conditions
ConditionsYield
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
527-61-7

2,6-dimethyl-1,4-benzoquinone

dibenzylamine
103-49-1

dibenzylamine

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2-((dibenzylamino)methyl)-6-methylbenzene-1,4-diol

2-((dibenzylamino)methyl)-6-methylbenzene-1,4-diol

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 70℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere;A 6%
B 94%
4-hydroxy-3,5-dimethylbenzaldehyde
2233-18-3

4-hydroxy-3,5-dimethylbenzaldehyde

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
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%
2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

1-(1-methyl-1H-imidazol-2-yl)-2-phenylethan-1-one

1-(1-methyl-1H-imidazol-2-yl)-2-phenylethan-1-one

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2-(3,6-dihydroxy-2,4-dimethylphenyl)-1-(1-methyl-1Himidazol-2-yl)-2-phenylethanone

2-(3,6-dihydroxy-2,4-dimethylphenyl)-1-(1-methyl-1Himidazol-2-yl)-2-phenylethanone

Conditions
ConditionsYield
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
187873-55-8

2,6-dimethyl-cyclohex-3-ene-1,2-diol

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

Conditions
ConditionsYield
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h;A 71%
B 6%
4-hydroxy-3,5-dimethylbenzaldehyde
2233-18-3

4-hydroxy-3,5-dimethylbenzaldehyde

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

Conditions
ConditionsYield
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
78877-83-5

4-(cyclopenten-1-yl)-2,6-dimethylphenol

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
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
750624-36-3

1,3-dimethyl-2,5-bis-prop-2-ynyloxy-benzene

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

3,5-dimethyl-4-prop-2-ynyloxy-phenol
750624-43-2

3,5-dimethyl-4-prop-2-ynyloxy-phenol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 0.5h;A 6%
B 55%
2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

A

ditropenyl
831-18-5

ditropenyl

B

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

C

2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone
60457-35-4

2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone

Conditions
ConditionsYield
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
527-61-7

2,6-dimethyl-1,4-benzoquinone

Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

A

ditropenyl
831-18-5

ditropenyl

B

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

C

2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone
60457-35-4

2-Cyclohepta-2,4,6-trienyl-3,5-dimethyl-[1,4]benzoquinone

Conditions
ConditionsYield
In toluene for 1.5h; Heating;A 6%
B 40 mg
C 14%
3,4-dimethyl-quinoline
2436-92-2

3,4-dimethyl-quinoline

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
With sulfuric acid
4-methoxy-2,6-dimethylphenol
2431-91-6

4-methoxy-2,6-dimethylphenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
With hydrogen bromide
3,5-dimethyl-4-aminophenol
3096-70-6

3,5-dimethyl-4-aminophenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride; sodium dithionite; iron(III) chloride Multistep reaction;
3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
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
527-61-7

2,6-dimethyl-1,4-benzoquinone

methyllithium
917-54-4

methyllithium

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

1,2,4,6-Tetramethyl-cyclohexa-2,5-diene-1,4-diol

1,2,4,6-Tetramethyl-cyclohexa-2,5-diene-1,4-diol

Conditions
ConditionsYield
ether, THF, -78 deg C; 60 min; Yield given. Multistep reaction. Yields of byproduct given;
O-(2,6-dimethylphenyl)hydroxylamine
144181-59-9

O-(2,6-dimethylphenyl)hydroxylamine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

B

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

C

N-(3,5-dimethyl-4-hydroxyphenyl)trifluoroacetamide

N-(3,5-dimethyl-4-hydroxyphenyl)trifluoroacetamide

2,2,2-Trifluoro-N-[(1S,2S,7R,8R)-3,5,8,11-tetramethyl-4,12-dioxo-11-(2,2,2-trifluoro-acetylamino)-tricyclo[6.2.2.02,7]dodeca-5,9-dien-3-yl]-acetamide

2,2,2-Trifluoro-N-[(1S,2S,7R,8R)-3,5,8,11-tetramethyl-4,12-dioxo-11-(2,2,2-trifluoro-acetylamino)-tricyclo[6.2.2.02,7]dodeca-5,9-dien-3-yl]-acetamide

Conditions
ConditionsYield
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;
2,6-dimethyl-4-nitro phenol
2423-71-4

2,6-dimethyl-4-nitro phenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
Multistep reaction;
4-hydroxy-3,5-dimethylphenyl acetate
880-06-8

4-hydroxy-3,5-dimethylphenyl acetate

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
With sulfuric acid Heating;
2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

3,5-dimethyl-2-(p-tolylthio)benzene-1,4-diol
30771-69-8

3,5-dimethyl-2-(p-tolylthio)benzene-1,4-diol

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

3,5-Dimethyl-2-p-tolylsulfanyl-[1,4]benzoquinone

3,5-Dimethyl-2-p-tolylsulfanyl-[1,4]benzoquinone

Conditions
ConditionsYield
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
527-61-7

2,6-dimethyl-1,4-benzoquinone

3,5-dimethyl-2-(phenylsulfonyl)benzene-1,4-diol
30771-74-5

3,5-dimethyl-2-(phenylsulfonyl)benzene-1,4-diol

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2,6-dimethyl-3-phenylsulfonyl-1,4-benzoquinone
145746-46-9

2,6-dimethyl-3-phenylsulfonyl-1,4-benzoquinone

Conditions
ConditionsYield
With sodium acetate In methanol; water at 24℃; Equilibrium constant;
2,6-Dimethyl-4-(4-nitro-phenylazo)-phenol
1778-65-0

2,6-Dimethyl-4-(4-nitro-phenylazo)-phenol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
(i) Zn, aq. H2SO4, (ii) Fe2(SO4)3, (iii) aq. Na2S2O4, benzene; Multistep reaction;
2,6-dimethyl-1,4-benzosemiquinone anion radical
87810-92-2

2,6-dimethyl-1,4-benzosemiquinone anion radical

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

Conditions
ConditionsYield
In water at 22℃; Rate constant;
3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

K2S2O8

K2S2O8

aqueous NaOH

aqueous NaOH

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
Erwaermen mit wss. HCl;
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

K2S2O8

K2S2O8

aqueous NaOH

aqueous NaOH

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

Conditions
ConditionsYield
Erwaermen der Reaktionsloesung mit wss. HCl;
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

sulfuric acid
7664-93-9

sulfuric acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

iron(II) sulfate

iron(II) sulfate

acetic acid
64-19-7

acetic acid

A

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

B

3,3',5,5'-tetramethyldiphenoquinone
4906-22-3

3,3',5,5'-tetramethyldiphenoquinone

C

3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl
2417-04-1

3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

2,6-dimethyl-1,4-benzoquinone
527-61-7

2,6-dimethyl-1,4-benzoquinone

Conditions
ConditionsYield
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
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-benzene
850165-67-2

2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-benzene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 12h;95%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

(3,6-dihydroxy-2,4-dimethylphenyl)-(4-pyridyl)methanol

(3,6-dihydroxy-2,4-dimethylphenyl)-(4-pyridyl)methanol

Conditions
ConditionsYield
With hydrogenchloride for 17h; Ambient temperature;93%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

(3,6-dihydroxy-2,4-dimethylphenyl)-(2-pyridyl)methanol

(3,6-dihydroxy-2,4-dimethylphenyl)-(2-pyridyl)methanol

Conditions
ConditionsYield
With hydrogenchloride for 37h; Ambient temperature;92%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

(3,6-dihydroxy-2,4-dimethylphenyl)-(3-pyridyl)methanol
162653-09-0

(3,6-dihydroxy-2,4-dimethylphenyl)-(3-pyridyl)methanol

Conditions
ConditionsYield
With hydrogenchloride for 17h; Ambient temperature;91%
tert-Butyl chloroacetate
107-59-5

tert-Butyl chloroacetate

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

tert-butyl 2-(4-formyl-3,5-dimethylphenoxy)acetate

tert-butyl 2-(4-formyl-3,5-dimethylphenoxy)acetate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 3h;89%
methanol
67-56-1

methanol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

4-methoxy-2,6-dimethylphenol
2431-91-6

4-methoxy-2,6-dimethylphenol

Conditions
ConditionsYield
With sulfuric acid Heating;87%
With sulfuric acid
deuteromethanol
1455-13-6

deuteromethanol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

4-Methoxy-2,6-dimethyl<3,5-D2>phenol

4-Methoxy-2,6-dimethyl<3,5-D2>phenol

Conditions
ConditionsYield
With sulfuric acid-d2 Heating;85%
1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

methyl iodide
74-88-4

methyl iodide

1,3-dimethyl-2,5-dimethoxybenzene
14538-50-2

1,3-dimethyl-2,5-dimethoxybenzene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide84%
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
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

trans-2,3-diphenyloxirane

trans-2,3-diphenyloxirane

trans-4,6-dimethyl-2,3-diphenyl-2,3-dihydrobenzofuran-5-ol

trans-4,6-dimethyl-2,3-diphenyl-2,3-dihydrobenzofuran-5-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In chloroform at 20℃; for 1h;80%
2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

2,2,5,7-tetramethyl-6-chromanol
14074-92-1

2,2,5,7-tetramethyl-6-chromanol

Conditions
ConditionsYield
With hydrogenchloride; silica gel; zinc(II) chloride In tetrachloromethane for 1.33333h; Heating;79%
2-hydroxy-2-methylbut-3-enenitrile
75819-97-5

2-hydroxy-2-methylbut-3-enenitrile

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

6-hydroxy-2,5,7-trimethyl-2-cyanochromane
75820-00-7

6-hydroxy-2,5,7-trimethyl-2-cyanochromane

Conditions
ConditionsYield
With phosphoric acid In nitromethane; boron trifluoride; toluene79%
vinyl propionate
105-38-4

vinyl propionate

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

A

4-O-propanoyl-2,6-dimethylhydroquinone

4-O-propanoyl-2,6-dimethylhydroquinone

B

1-O-propanoyl-2,6-dimethylhydroquinone

1-O-propanoyl-2,6-dimethylhydroquinone

Conditions
ConditionsYield
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
924-50-5

Methyl 3,3-dimethylacrylate

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin
50442-68-7

6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin

Conditions
ConditionsYield
With methanesulfonic acid at 70℃; for 2h;76.9%
With sulfuric acid In benzene63%
With sulfuric acid In benzene for 3h; Heating;40%
With methanesulfonic acid at 70℃; for 1.5h;
methanol
67-56-1

methanol

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

2-Methoxy-2,5,7-trimethyl-chroman-6-ol
121175-03-9

2-Methoxy-2,5,7-trimethyl-chroman-6-ol

Conditions
ConditionsYield
With sulfuric acid74%
1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

isobutyraldehyde
78-84-2

isobutyraldehyde

2,3-dihydro-5-hydroxy-2,2,4,6-tetramethylbenzofuran
118112-01-9

2,3-dihydro-5-hydroxy-2,2,4,6-tetramethylbenzofuran

Conditions
ConditionsYield
With hydrogenchloride In water; toluene for 12h; Reflux;74%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

2,2'-(2,6-dimethyl-1,4-phenylenedioxy)diethanol

2,2'-(2,6-dimethyl-1,4-phenylenedioxy)diethanol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 140℃;73%
1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

propargyl bromide
106-96-7

propargyl bromide

1,3-dimethyl-2,5-bis-prop-2-ynyloxy-benzene
750624-36-3

1,3-dimethyl-2,5-bis-prop-2-ynyloxy-benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 80℃;73%
1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

(E)-6-chloro-3-methyl-2-hexene-1-ol
118607-88-8

(E)-6-chloro-3-methyl-2-hexene-1-ol

2-(3-chloropropyl)-2,5,7-trimethyl-6-chromanol
155439-88-6

2-(3-chloropropyl)-2,5,7-trimethyl-6-chromanol

Conditions
ConditionsYield
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
541-47-9

3-Methylbutenoic acid

1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin
50442-68-7

6-hydroxy-4,4,5,7-tetramethyl-3,4-dihydrocoumarin

Conditions
ConditionsYield
With methanesulfonic acid at 70℃; for 18h;67%
In various solvent(s) at 70℃;
With methanesulfonic acid at 70℃;
1,4-dihydroxy-2,6-dimethylbenzene
654-42-2

1,4-dihydroxy-2,6-dimethylbenzene

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

C29H22O8

C29H22O8

Conditions
ConditionsYield
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%

2,6-Dimethylhydroquinone Specification

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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