3-Chlorophenol

3-Chlorophenol
3-Chlorophenol
Names
Preferred IUPAC name
3-Chlorophenol[1]
Other names
m-Chlorophenol
meta-Chlorophenol
3-Hydroxychlorobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.257 Edit this at Wikidata
UNII
  • InChI=1S/C6H5ClO/c7-5-2-1-3-6(8)4-5/h1-4,8H
    Key: HORNXRXVQWOLPJ-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)Cl)O
Properties
C6H5ClO
Molar mass 128.56 g·mol−1
Appearance Colorless or white oily solid
Density 1.245 g/cm3 at 45 °C[2]
Melting point 32.5 °C (90.5 °F; 305.6 K)[2]
Boiling point 210 °C (410 °F; 483 K)[2]
20 g/L at 20 °C
Solubility in other solvents Soluble in ethanol, diethyl ether, benzene
Acidity (pKa) 9.12[3]
-77.6·10−6 cm3/mol[4]
1.5565[2]
Thermochemistry[5]
-206.4 kJ·mol−1 (s)
−189.3 kJ·mol−1 (l)
Enthalpy of fusion (ΔfH⦵fus)
 14.9 kJ·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive – causes burns
Flash point 120 °C (248 °F; 393 K)
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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3-Chlorophenol is an organic compound with the molecular formula C6H4ClOH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene.[6]

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. ^ a b c d Haynes, p. 3.116
  3. ^ Haynes, p. 5.90
  4. ^ Haynes, p. 3.577
  5. ^ Haynes, pp. 5.10, 6.156
  6. ^ François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.

Cited sources