2-Chlorophenol

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2-Chlorophenol
2-Chlorophenol 2-Chlorphenol.svg
2-Chlorophenol
2-Chlorophenol 2-chlorophenol.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H Yes check.svgY
    Key: ISPYQTSUDJAMAB-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless 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 (ΔfH⦵fus)
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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2-Chlorophenol or ortho-chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three isomers of monochlorophenol. Aside 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.

Contents

See also

Related Research Articles

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<span class="mw-page-title-main">Catechol</span> Organic compound (C6H4(OH)2); benzene with two adjacent –OH groups

Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.

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Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

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<span class="mw-page-title-main">4-Aminophenol</span> Chemical compound

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.

3-Aminophenol is an organic compound with formula C6H4(NH2)(OH). It is an aromatic amine and a phenol. It is the meta isomer of 2-aminophenol and 4-aminophenol.

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<span class="mw-page-title-main">2,4,6-Trichlorophenol</span> Chemical compound

2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.

<span class="mw-page-title-main">2-Aminophenol</span> Chemical compound

2-Aminophenol is an organic compound with the formula C6H7NO. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallized from hot water.

<span class="mw-page-title-main">Diphenyl ether</span> Chemical compound

Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications.

In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among all possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it is important to decide on a unique name. It is intended for use in legal and regulatory situations.

2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).

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<span class="mw-page-title-main">3-Chlorophenol</span> Chemical compound

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.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

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 (inactive 2024-06-30). 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.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)
  2. 1 2 3 4 Haynes, p. 3.116
  3. ↑ Haynes, p. 16.20
  4. ↑ Haynes, p. 5.90
  5. ↑ Haynes, p. 3.577
  6. 1 2 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.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   978-3527306732.

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