tert-Amyl alcohol

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tert-Amyl alcohol
Tert-Amyl alcohol low purity forerun high purity end run by NurdRage.jpg
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
229.3 J·K−1·mol−1
−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):
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.

Properties

Chemical

tert-Amyl alcohol, like all tertiary alcohols, is not readily oxidized. Due to the high stability of the tert-amyl cation, it is quite easy to prepare tert-amyl halides by reaction of the alcohol with the corresponding hydrogen halide 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 bought online.

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.

References

Relevant Sciencemadness threads