tert-Butanol

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tert-Butanol
Names
IUPAC name
2-Methylpropan-2-ol
Other names
2-Methyl-2-propanol
tert-Butyl alcohol
t-BuOH
Trimethyl carbinol
TBA
Identifiers
Jmol-3D images Image
Properties
(CH3)3COH
C4H10O
Molar mass 74.12 g/mol
Appearance Colorless solid (<25 °C) or liquid (>25 °C)
Odor Camphorous
Density 0.7886 g/cm3 (at 20 °C)
Melting point 25.81 °C (78.46 °F; 298.96 K)
Boiling point 82.3 °C (180.1 °F; 355.4 K)
Miscible
Solubility Miscible with diethyl ether, ethanol, isopropanol
Soluble in chloroform
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 16.54
Thermochemistry
189.5 J·K−1·mol−1
−360.04–−358.36 kJ·mol−1
Hazards
Safety data sheet ScienceLab
Flash point 11 °C
Lethal dose or concentration (LD, LC):
3559 mg/kg (rabbit, oral)
3500 mg/kg (rat, oral)
Related compounds
Related compounds
Butanol
sec-Butanol
Isobutanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

tert-Butanol or tert-Butyl alcohol (TBA), also known as 2-methylpropan-2-ol (2M2P), is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes shortened to t-BuOH). One of the most interesting characteristics of t-BuOH is that it can be a clear liquid or a colorless solid depending on the ambient temperature and season, with a melting point around 25 °C.

Properties

Chemical

Being a tertiary alcohol, tert-butanol cannot be oxidized to an aldehyde or ketone.

Physical

tert-Butanol is a colorless solid at standard conditions, but has a very high melting point for a simple alcohol, of only 25.8 °C. It's boiling point is 82.3 °C. t-BuOH is miscible with water and has a camphor-like smell.

Availability

t-BuOH is sold by various chemical suppliers.

It can also be found as fuel additive, though the percentage is small.

Small amounts are sometimes added in rubbing alcohol as a denaturing agent.

Preparation

tert-Butanol can be made via acid catalyzed hydrolysis of methyl tert-butyl ether.

A more complex way is by reacting acetone with methylmagnesium halide

Projects

Handling

Safety

tert-Butanol poses low toxicity, though it can be irritant. It is also flammable.

Storage

tert-Butanol should be stored in closed bottles, preferably glass. If the temperature inside the storage area drops below 25 °C, such as during cold seasons, rain or night, t-BuOH will freeze. This is not usually a problem, as it does not expand upon freezing and is also less volatile when solid, but getting it out of the bottle may become frustrating.

Disposal

tert-Butanol can be safely burned, either pure or dissolved in a more flammable solvent. It can also be destroyed with Fenton's reagent, though this is not always necessary.

References

Relevant Sciencemadness threads