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, 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.

References

Relevant Sciencemadness threads