Difference between revisions of "Benzyl alcohol"
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| OtherNames = Benzenemethanol<br>Hydroxytoluene<br>Phenylcarbinol | | OtherNames = Benzenemethanol<br>Hydroxytoluene<br>Phenylcarbinol | ||
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| − | | ImageFile = | + | | ImageFile = Benzyl alcohol sample and amber bottle.jpg |
| − | | ImageSize = | + | | ImageSize = 300 |
| ImageAlt = | | ImageAlt = | ||
| ImageName = | | ImageName = | ||
| + | | ImageCaption = Benzyl alcohol sample and original bottle | ||
| ImageFile1 = | | ImageFile1 = | ||
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| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| − | | Odor = | + | | Odor = Weak, slightly aromatic |
| pKa = 15.40 | | pKa = 15.40 | ||
| pKb = | | pKb = | ||
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| LD50 = 1,250 mg/kg (rat, oral) | | LD50 = 1,250 mg/kg (rat, oral) | ||
| LC50 = | | LC50 = | ||
| − | | MainHazards = | + | | MainHazards = Irritant |
| NFPA-F = | | NFPA-F = | ||
| NFPA-H = | | NFPA-H = | ||
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| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = [[Phenol]] | + | | OtherCompounds = [[Phenol]]<br>[[Phenethyl alcohol]]<br>[[Diphenylmethanol]]<br>[[Triphenylmethanol]] |
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| − | '''Benzyl alcohol''' is an aromatic alcohol with the formula '''C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH''', commonly used in the production of various compounds and in the pharmaceutical industry. | + | '''Benzyl alcohol''' or '''phenylmethanol''' is an aromatic alcohol with the formula '''C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH''', commonly used in the production of various compounds and in the pharmaceutical industry. |
| − | The ''benzyl'' group is often abbreviated "Bn" (not to be confused with "Bz" which is used for ''benzoyl''), thus benzyl alcohol is denoted as '''BnOH'''. | + | The ''benzyl'' group is often abbreviated "Bn" (not to be confused with "Bz" which is used for ''benzoyl''), thus benzyl alcohol is often denoted as '''BnOH'''. |
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
Benzyl alcohol can be oxidized to [[benzaldehyde]] and [[benzoic acid]]. | Benzyl alcohol can be oxidized to [[benzaldehyde]] and [[benzoic acid]]. | ||
| + | |||
| + | Reaction with concentrated haloacids yields benzyl halides. Reaction with [[hydrochloric acid]], for example, gives [[benzyl chloride]]. | ||
| + | |||
| + | : C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH + HCl → C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>Cl + H<sub>2</sub>O | ||
===Physical=== | ===Physical=== | ||
| − | Benzyl alcohol is a colorless liquid, slightly soluble in water. | + | Benzyl alcohol is a colorless liquid, almost odorless, slightly soluble in water. |
==Availability== | ==Availability== | ||
Benzyl alcohol is sold by chemical suppliers. Can also be purchased online. | Benzyl alcohol is sold by chemical suppliers. Can also be purchased online. | ||
| − | Benzyl alcohol can sometimes be found in hardware stores as solvent, though most of the time mixed with other solvents. | + | Benzyl alcohol can sometimes be found in hardware and art/painting stores as solvent, mostly pure, though most of the time mixed with other solvents. |
| − | Some window cleaning products | + | Some window cleaning products and mouthwashers contain benzyl alcohol, albeit in a small percentage. |
==Preparation== | ==Preparation== | ||
| − | Can be prepared by hydrolyzing [[benzyl chloride]] with [[sodium hydroxide]]. | + | Can be prepared by hydrolyzing [[benzyl chloride]] with [[sodium hydroxide]]. |
| + | |||
| + | : C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>Cl + NaOH → C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH + NaCl | ||
| + | |||
| + | The benzyl chloride used for the reaction can be obtained by chlorinating [[toluene]] under UV light. | ||
==Projects== | ==Projects== | ||
*Make benzyl chloride | *Make benzyl chloride | ||
| + | *Make benzaldehyde | ||
*Make perfumes | *Make perfumes | ||
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===Storage=== | ===Storage=== | ||
| − | + | Benzyl alcohol should be kept in closed bottles, preferably in air-tight bottles, if you intend to store it for long periods of time. | |
===Disposal=== | ===Disposal=== | ||
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[[Category:Chemical compounds]] | [[Category:Chemical compounds]] | ||
[[Category:Organic compounds]] | [[Category:Organic compounds]] | ||
| + | [[Category:Aromatic compounds]] | ||
[[Category:Alcohols]] | [[Category:Alcohols]] | ||
| + | [[Category:Primary alcohols]] | ||
[[Category:Aromatic alcohols]] | [[Category:Aromatic alcohols]] | ||
[[Category:Solvents]] | [[Category:Solvents]] | ||
Latest revision as of 10:50, 9 September 2023
 Benzyl alcohol sample and original bottle
| |
| Names | |
|---|---|
| IUPAC name
Phenylmethanol
| |
| Other names
Benzenemethanol
Hydroxytoluene Phenylcarbinol | |
| Properties | |
| C7H8O C6H5CH2OH | |
| Molar mass | 108.14 g/mol |
| Appearance | Colorless liquid |
| Odor | Weak, slightly aromatic |
| Density | 1.044 g/cm3 |
| Melting point | −15.2 °C (4.6 °F; 257.9 K) |
| Boiling point | 205.3 °C (401.5 °F; 478.4 K) |
| 3.50 g/100 ml (20 °C) 4.29 g/100 ml (25 °C) | |
| Solubility | Miscible in acetone, benzene, chloroform, diethyl ether, ethanol, methanol |
| Vapor pressure | 0.18 kPa (60 °C) |
| Acidity (pKa) | 15.40 |
| Thermochemistry | |
| Std molar
entropy (S |
217.8 J·mol-1K-1 |
| Std enthalpy of
formation (ΔfH |
-352 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 93 °C (199 °F; 366 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
1,250 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Phenol Phenethyl alcohol Diphenylmethanol Triphenylmethanol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzyl alcohol or phenylmethanol is an aromatic alcohol with the formula C6H5CH2OH, commonly used in the production of various compounds and in the pharmaceutical industry.
The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is often denoted as BnOH.
Contents
Properties
Chemical
Benzyl alcohol can be oxidized to benzaldehyde and benzoic acid.
Reaction with concentrated haloacids yields benzyl halides. Reaction with hydrochloric acid, for example, gives benzyl chloride.
- C6H5CH2OH + HCl → C6H5CH2Cl + H2O
Physical
Benzyl alcohol is a colorless liquid, almost odorless, slightly soluble in water.
Availability
Benzyl alcohol is sold by chemical suppliers. Can also be purchased online.
Benzyl alcohol can sometimes be found in hardware and art/painting stores as solvent, mostly pure, though most of the time mixed with other solvents.
Some window cleaning products and mouthwashers contain benzyl alcohol, albeit in a small percentage.
Preparation
Can be prepared by hydrolyzing benzyl chloride with sodium hydroxide.
- C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl
The benzyl chloride used for the reaction can be obtained by chlorinating toluene under UV light.
Projects
- Make benzyl chloride
- Make benzaldehyde
- Make perfumes
Handling
Safety
Benzyl alcohol has low toxicity and has low volatility. It is however, severely toxic and highly irritating to the eye.
Storage
Benzyl alcohol should be kept in closed bottles, preferably in air-tight bottles, if you intend to store it for long periods of time.
Disposal
No special disposal is required.
