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95-71-6

Basic Information
CAS No.: 95-71-6
Name: 2-Methylhydroquinone
Article Data: 127
Molecular Structure:
Molecular Structure of 95-71-6 (2-Methylhydroquinone)
Formula: C7H8O2
Molecular Weight: 124.139
Synonyms: Hydroquinone,methyl- (6CI,8CI);1,4-Dihydroxy-2-methylbenzene;2,5-Dihydroxytoluene;2,5-Toluenediol;2-Methyl-1,4-benzenediol;2-Methyl-1,4-dihydroxybenzene;2-Methyl-1,4-hydroquinone;2-Methyl-p-hydroquinone;4-Hydroxy-2-methylphenol;M-HQ;Methyl-p-hydroquinone;Methylhydroquinone;
EINECS: 202-443-7
Density: 1.21 g/cm3
Melting Point: 128-130 °C(lit.)
Boiling Point: 277.8 °C at 760 mmHg
Flash Point: 140.2 °C
Solubility: 77 g/L (25 °C) in water
Appearance: white solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-22
Safety: 26-36
Transport Information: UN 2811
PSA: 40.46000
LogP: 1.40620
Synthetic route
108-39-4

3-methyl-phenol

A

95-71-6

2-methylbenzene-1,4-diol

B

553-97-9

2-Methyl-1,4-benzoquinone

Conditions
ConditionsYield
With dihydrogen peroxide; Ti-superoxide In water; acetic acid for 1.25h; Product distribution / selectivity; Heating / reflux;A 0.5%
B 99%
553-97-9

2-Methyl-1,4-benzoquinone

95-71-6

2-methylbenzene-1,4-diol

Conditions
ConditionsYield
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%
95-48-7

ortho-cresol

95-71-6

2-methylbenzene-1,4-diol

Conditions
ConditionsYield
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℃;
95-48-7

ortho-cresol

A

95-71-6

2-methylbenzene-1,4-diol

B

553-97-9

2-Methyl-1,4-benzoquinone

Conditions
ConditionsYield
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;
553-97-9

2-Methyl-1,4-benzoquinone

A

95-71-6

2-methylbenzene-1,4-diol

B

1,2,4-Trimethyl-cyclohexa-2,5-diene-1,4-diol

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h;A 9%
B 91%
133411-19-5

1,4-O-di-propanoylmethylhydroquinone

A

1-O-propanoyl-2-methylhydroquinone

B

4-O-propanoyl-2-methylhydroquinone

C

95-71-6

2-methylbenzene-1,4-diol

Conditions
ConditionsYield
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%
78877-82-4

4-(cyclopenten-1-yl)-o-cresol

A

95-71-6

2-methylbenzene-1,4-diol

B

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 70.3%
B n/a
553-97-9

2-Methyl-1,4-benzoquinone

/PBCEG004--930/

/PBCEG004--930/

A

95-71-6

2-methylbenzene-1,4-diol

B

2-(4-Chloro-phenylamino)-3-methyl-[1,4]benzoquinone

C

1602-00-2

bis-(4-chloro-phenyl)-diazene

Conditions
ConditionsYield
In tetrahydrofuran 0 deg C, 1 h, RT, 1 h, 55 deg C, 0.5 h;A 67%
B 9%
C 6%
108-39-4

3-methyl-phenol

95-71-6

2-methylbenzene-1,4-diol

Conditions
ConditionsYield
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

A

95-71-6

2-methylbenzene-1,4-diol

B

2-Methyl-2-(4-methyl-thiazol-2-ylsulfanylmethyl)-cyclopentane-1,3-dione

Conditions
ConditionsYield
In toluene Heating;A 20%
B 43%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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,