Difference between revisions of "Phenolphthalein"
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(Created page with "{{Chembox | Name = Phenolphthalein | Reference = | IUPACName = 3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one | PIN = | SystematicName = Phenolphthalein | OtherNames = HIn<br...") |
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| OtherNames = HIn<br>phph | | OtherNames = HIn<br>phph | ||
<!-- Images --> | <!-- Images --> | ||
| − | | ImageFile = Phenolphthalein sample | + | | ImageFile = Phenolphthalein bottle sample solutions.jpg |
| ImageSize = 300 | | ImageSize = 300 | ||
| ImageAlt = | | ImageAlt = | ||
| ImageName = | | ImageName = | ||
| − | | ImageCaption = Phenolphthalein sample ( | + | | ImageCaption = Phenolphthalein sample (center) with original bottle (left) and in solution at acidic and neutral pH (colorless) and basic pH (pink) |
| ImageFile1 = | | ImageFile1 = | ||
| ImageSize1 = | | ImageSize1 = | ||
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| MeltingPt_ref = <ref>Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4 3297</ref> | | MeltingPt_ref = <ref>Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4 3297</ref> | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| + | | Odor = Odorless | ||
| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = 0.04 g/100 ml |
| SolubleOther = Very soluble in [[acetone]], [[ethanol]] and pyrene<br>Soluble in [[chloroform]], [[diethyl ether]], and [[toluene]]<br>Slightly soluble in [[carbon disulfide]]<br>Insoluble in [[benzene]], [[hexane]], [[petroleum ether]] | | SolubleOther = Very soluble in [[acetone]], [[ethanol]] and pyrene<br>Soluble in [[chloroform]], [[diethyl ether]], and [[toluene]]<br>Slightly soluble in [[carbon disulfide]]<br>Insoluble in [[benzene]], [[hexane]], [[petroleum ether]] | ||
| Solvent = | | Solvent = | ||
| Line 112: | Line 113: | ||
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | + | Phenolphthalein is colorless at acidic and neutral pH and pink at basic [[pH]]. | |
===Physical=== | ===Physical=== | ||
| − | Phenolphthalein is a white solid, poorly soluble in water but very soluble in ethanol. | + | Phenolphthalein is a white solid, poorly soluble in water but very soluble in [[acetone]] and [[ethanol]]. |
==Availability== | ==Availability== | ||
| Line 122: | Line 123: | ||
==Preparation== | ==Preparation== | ||
Phenolphthalein can be prepared by reacting [[phenol]] with [[phthalic anhydride]], in the presence of anhydrous [[aluminium chloride]] and [[zinc chloride]]. [[Thionyl chloride]] can substitute aluminium chloride. | Phenolphthalein can be prepared by reacting [[phenol]] with [[phthalic anhydride]], in the presence of anhydrous [[aluminium chloride]] and [[zinc chloride]]. [[Thionyl chloride]] can substitute aluminium chloride. | ||
| + | |||
| + | :2 C<sub>6</sub>H<sub>5</sub>OH + C<sub>6</sub>H<sub>4</sub>C<sub>2</sub>O<sub>3</sub> → C<sub>20</sub>H<sub>14</sub>O<sub>4</sub> | ||
==Projects== | ==Projects== | ||
*Base indicator | *Base indicator | ||
| + | *Ferroxyl indicator solution | ||
| + | *Kastle–Meyer test | ||
==Handling== | ==Handling== | ||
===Safety=== | ===Safety=== | ||
| + | Phenolphthalein, if taken orally, is mildly toxic, a suspected carcinogen and a powerful laxative. Several decades ago, it was commonly used as such in medicine. Today, less toxic laxatives are used. | ||
===Storage=== | ===Storage=== | ||
| + | Phenolphthalein should be kept in closed bottles, away from acidic vapors. | ||
===Disposal=== | ===Disposal=== | ||
| + | Can be destroyed with a strong oxidizer, such as [[Fenton's reagent]], [[chromic acid]] or [[piranha solution]], neutralized and poured down the drain. | ||
| + | |||
| + | ==Gallery== | ||
| + | <gallery widths="200" position="center" columns="4" orientation="none"> | ||
| + | Phenolphthalein_solution.jpg|Phenolphthalein's color in basic solution. | ||
| + | Phenolphthalein sample with acid and base solutions.jpg|Phenolphthalein sample (middle), and dissolved in an acid (left) and a base (right). | ||
| + | </gallery> | ||
==References== | ==References== | ||
| Line 144: | Line 158: | ||
[[Category:Phenols]] | [[Category:Phenols]] | ||
[[Category:PH indicators]] | [[Category:PH indicators]] | ||
| + | [[Category:Essential reagents]] | ||
Latest revision as of 14:55, 18 November 2023
 Phenolphthalein sample (center) with original bottle (left) and in solution at acidic and neutral pH (colorless) and basic pH (pink)
| |
| Names | |
|---|---|
| IUPAC name
3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one
| |
| Systematic IUPAC name
Phenolphthalein | |
| Other names
HIn
phph | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| C20H14O4 | |
| Molar mass | 318.33 g/mol |
| Appearance | White powder |
| Odor | Odorless |
| Density | 1.3 g/cm3 (at 20 °C) |
| Melting point | 262.5 °C (504.5 °F; 535.6 K)[1] |
| Boiling point | Decomposes |
| 0.04 g/100 ml | |
| Solubility | Very soluble in acetone, ethanol and pyrene Soluble in chloroform, diethyl ether, and toluene Slightly soluble in carbon disulfide Insoluble in benzene, hexane, petroleum ether |
| Vapor pressure | 6.7·10-13 mm Hg at 25 °C |
| Hazards | |
| Safety data sheet | Acros Organics |
| Flash point | Non-flammable |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Phenolphthalein is an organic chemical compound, often used as an indicator in acid–base titrations. For this application, it turns colorless in acidic solutions and pink in basic solutions.
Contents
Properties
Chemical
Phenolphthalein is colorless at acidic and neutral pH and pink at basic pH.
Physical
Phenolphthalein is a white solid, poorly soluble in water but very soluble in acetone and ethanol.
Availability
Phenolphthalein is sold by various chemical suppliers.
Preparation
Phenolphthalein can be prepared by reacting phenol with phthalic anhydride, in the presence of anhydrous aluminium chloride and zinc chloride. Thionyl chloride can substitute aluminium chloride.
- 2 C6H5OH + C6H4C2O3 → C20H14O4
Projects
- Base indicator
- Ferroxyl indicator solution
- Kastle–Meyer test
Handling
Safety
Phenolphthalein, if taken orally, is mildly toxic, a suspected carcinogen and a powerful laxative. Several decades ago, it was commonly used as such in medicine. Today, less toxic laxatives are used.
Storage
Phenolphthalein should be kept in closed bottles, away from acidic vapors.
Disposal
Can be destroyed with a strong oxidizer, such as Fenton's reagent, chromic acid or piranha solution, neutralized and poured down the drain.
Gallery
Phenolphthalein's color in basic solution.
Phenolphthalein sample (middle), and dissolved in an acid (left) and a base (right).
References
- ↑ Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4 3297
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- Chemical compounds
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