Resorcinol

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Resorcinol
Resorcinol.jpg
Sample of resorcinol
Names
IUPAC name
Benzene-1,3-diol
Other names
1,3-Benzenediol
1,3-Dihydroxybenzene
3-Hydroxyphenol
m-Benzenediol
m-Dihydroxybenzene
m-Hydroquinone
Resorcin
Properties
C6H6O2
C6H4(OH)/2
Molar mass 110.1 g/mol
Appearance White solid
Odor Faint, characteristic aromatic odor
Density 1.28 g/cm3
Melting point 110 °C (230 °F; 383 K)
Boiling point 277 °C (531 °F; 550 K)
110 g/100 ml at 20 °C
Solubility Soluble in acetone, carbon tetrachloride, diethyl ether, DMSO, ethanol, glycerol, isopropanol, methanol
Insoluble in benzene, carbon disulfide, chloroform
Vapor pressure 0.0002 mmHg (25 °C)
Acidity (pKa) 9.30
11.06
Thermochemistry
Hazards
Safety data sheet Sigma-Aldrich
Flash point 127 °C (260.6 °F; 400 K)
Related compounds
Related compounds
Phenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Resorcinol (or resorcin) is an organic compound with the chemical formula C6H4(OH)/2.

Properties

Chemical

Resorcinol reduces Fehling's solution and ammoniacal silver solutions.

When fused with potassium hydroxide, resorcinol yields phloroglucin.

When resorcinol is mixed with sodium nitrite, a water-soluble blue dye, which is turned red by acids, and is used as an indicator, under the name of lacmoid.

Nitration with concentrated nitric acid in the presence of cold concentrated sulfuric acid (nitrating mixture) yields trinitro-resorcin (styphnic acid), an explosive.

Physical

Resorcinol is a white crystalline solid that becomes pink on exposure to light and air.

Availability

Resorcinol is sold by chemical suppliers.

Some over-the-counter topical acne treatments contain 2% resorcinol.

Preparation

Resorcinol is produced in several steps from benzene, starting with dialkylation with propylene to give 1,3-diisopropylbenzene. Oxidation and Hock rearrangement of this disubstituted arene gives acetone and resorcinol.

Projects

  • Make dyes
  • Make pH indicator
  • Make styphnic acid

Handling

Safety

Resorcinol is irritant and should be handled with care. In large amounts is toxic, and can be absorbed through skin.

Storage

In closed bottles.

Disposal

Should be diluted with water and poured down the drain.

References

Relevant Sciencemadness threads