2-Chlorophenol

2-Chlorophenol or ortho-chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three isomeric monochloride derivatives of phenol. As from occasional use as a disinfectant, it has few applications. It is an intermediate in the polychlorination of phenol.[8] 2-Chlorophenol is a colorless liquid, although commercial samples are often yellow or amber-colored. It has an unpleasant, penetrating (carbolic) odor. It is poorly soluble in water.

2-Chlorophenol
2-Chlorophenol
2-Chlorophenol
2-Chlorophenol
2-Chlorophenol
Names
Preferred IUPAC name
2-Chlorophenol[1]
Other names
o-Chlorophenol
ortho-Chlorophenol
2-Hydroxychlorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.213
KEGG
UNII
  • InChI=1S/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H checkY
    Key: ISPYQTSUDJAMAB-UHFFFAOYSA-N checkY
  • InChI=1/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H
    Key: ISPYQTSUDJAMAB-UHFFFAOYAM
  • Oc1ccccc1Cl
Properties
C6H5ClO
Molar mass 128.56 g·mol−1
Appearance colorless liquid
Density 1.2634 g/cm3 at 20 °C[2]
Melting point 8 °C (46 °F; 281 K)[2]
Boiling point 173.4 °C (344.1 °F; 446.5 K)[2]
20 g/L at 20 °C
Solubility Soluble in ethanol, diethyl ether, benzene
Vapor pressure 0.308 kPa[3]
Acidity (pKa) 8.56[4]
-77.3·10−6 cm3/mol[5]
1.5524[2]
Viscosity 3.59 mPa·s[6]
Thermochemistry[7]
188.7 J·mol−1·K−1
Enthalpy of fusion fHfus)
13.0 kJ·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive – causes burns
Flash point 64 °C (147 °F; 337 K)[6]
550 °C (1,022 °F; 823 K)
Safety data sheet (SDS) MSDS
Related compounds
benzene
phenol
chlorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

References

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
  2. Haynes, p. 3.116
  3. Haynes, p. 16.20
  4. Haynes, p. 5.90
  5. Haynes, p. 3.577
  6. Haynes, p. 6.243
  7. Haynes, pp. 5.10, 6.156
  8. Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.

Cited sources

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