10082. Xylenol

Nomenclature

CAS number: 1300-71-6
Dimethylphenol.
C8H10O; mol wt 122.16.
C 78.66%, H 8.25%, O 13.10%.
(CH3)2C6H3OH.

Description and references

Constituent of “cresylic acid.” There are 6 isomers of xylenol. They are only slightly sol in water but freely sol in alcohol, chloroform, ether, benzene, etc.; also sol in NaOH soln. Prepn and physical properties: R. J. L. Andon et al., J. Chem. Soc. 1960, 5246.

Derivative

2,3-Dimethylphenol.

Nomenclature

vic-o-Xylenol.

Properties

Needles from water or dil alc, mp 75°, bp 218°: Thl, Ber. 18, 2561 (1885); also reported as mp 72.57 ±0.02°, bp760 216.87 ±0.001° (Andon).

Derivative

2,4-Dimethylphenol.

Nomenclature

as-m-Xylenol.

Properties

Crystals, bp766 211.5°, mp 25.4-26°: Jacobsen, Ber. 11, 17 (1878); 18, 3463 (1885); also reported as mp 24.54 ±0.01°, bp760 210.931 ±0.001° (Andon).

Derivative

2,5-Dimethylphenol.

Nomenclature

p-Xylenol.

Properties

Crystals from alcohol + ether, mp 74.5°, bp762 211.5° (Jacobsen); bp 213.5°: Würtz, Ann. 147, 372 (1868); also reported as mp 74.85 ±0.02°, bp760 211.132 ±0.002° (Andon).

Derivative

2,6-Dimethylphenol.

Nomenclature

vic-m-Xylenol.

Properties

Needles, mp 49°, bp 203°: Gattermann, Ann. 357, 313 (1907); also reported as mp 45.62 ±0.01°, bp760 201.030 ±0.001° (Andon).

Derivative

3,4-Dimethylphenol.

Nomenclature

as-o-Xylenol.

Properties

Needles from water, mp 62.5°, bp 225°: Jacobsen, Ber. 17, 159 (1884); also reported as mp 65.11 ±0.01°, bp760 226.947 ±0.001° (Andon).

Derivative

3,5-Dimethylphenol.

Nomenclature

sym-m-Xylenol.

Properties

Needles from water, mp 64°, bp 219.5°: Thl, Ber. 18, 359 (1885); also reported as mp 63.27 ±0.02°, bp760 221.962 ±0.003° (Andon). LD50 orally in mice: 620 mg/kg: W. A. McOmie et al., J. Am. Pharm. Assoc. 38, 366 (1949).

Use

For the prepn of coal tar disinfectants; manuf of artificial resins.