tert-Amyl alcohol
 Low purity forerun (left) and high purity end run (right) tert-amyl alcohol, obtained via Grignard reaction route.
| |
| Names | |
|---|---|
| IUPAC name
2-Methylbutan-2-ol
| |
| Other names
2-Methyl-2-butanol
2-Methyl-2-butyl alcohol Amylene hydrate Dimethylethylcarbinol TAA t-Amylol t-Pentylol tert-Amyl alcohol tert-Pentyl alcohol | |
| Properties | |
| C5H12O CH3CH2(CH3)2C(OH) | |
| Molar mass | 88.15 g/mol |
| Appearance | Colorless liquid |
| Odor | Camphor-like |
| Density | 0.8096 g/cm3 (20 °C) |
| Melting point | −9 °C (16 °F; 264 K) |
| Boiling point | 102.4 °C (216.3 °F; 375.5 K) |
| 12 g/100 ml | |
| Solubility | Miscible with acetone, diethyl ether, benzene, chloroform, ethanol, glycerol, oils |
| Vapor pressure | 1.6 kPa (at 20 °C) |
| Thermochemistry | |
| Std molar
entropy (S |
229.3 J·K−1·mol−1 |
| Std enthalpy of
formation (ΔfH |
−380.0–−379.0 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 19 °C (66 °F; 292 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
1,000 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
tert-Butanol Pentanol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
tert-Amyl alcohol (TAA) or 2-methyl-2-butanol, is an isomer of pentanol and the second-smallest tertiary alcohol after the better-known tert-butanol.
Contents
Properties
Chemical
tert-Amyl alcohol, like all tertiary alcohols, resists oxidation to an aldehyde or carboxylic acid. Due to the high stability of its cation, it is quite easy to prepare tert-amyl halides from, reacting readily with hydrogen halides at room temperature.
Physical
tert-Amyl alcohol is a colorless liquid with a camphor-like odor. It is somewhat soluble in water, but miscible with other organic solvents, like alcohols and halocarbons.
Availability
tert-Pentanol is sold by chemical suppliers.
Can also be extracted via fractional distillation from fusel oil, though you will need large amounts of it.
Preparation
tert-Amyl alcohol can be prepared via the bromoethylethylmagnesium Grignard with acetone route.
NurdRage has a good video on this process.
Projects
Handling
Safety
tert-Amyl alcohol is flammable and a skin irritant. Ingestion or inhalation produces intoxication similar in many ways to ethanol, though it is around 20 times more potent by volume and produces longer-lasting effects. Exposure to vapor in the lab or accidental ingestion may cause temporary loss of physical and mental faculties or even sedation.
Storage
tert-Amyl alcohol should be kept in closed bottles made of glass or chemically resistant plastic such as HDPE, preferably in a flammables cabinet.
Disposal
Can be safely burned outside. Combustion products are not harmful.
