2-Methylpropan-2-ol

A tertiary alcohol that contrasts with primary and secondary oxidation examples.

Formula
C4H10O
Functional group
Tertiary alcohols
Molar mass
74.12 g/mol
Also known as
tert-Butanol, tert-Butyl alcohol, 2-Methyl-2-propanol, t-Butanol, T-BUTYL ALCOHOL, 1,1-Dimethylethanol

Overview

A tertiary alcohol that contrasts with primary and secondary oxidation examples.

The hydroxyl-bearing carbon is attached to three methyl groups and has no hydrogen. It therefore does not undergo the usual alcohol-to-carbonyl oxidation under the usual mild oxidation conditions. This restriction concerns that pathway; it does not mean the molecule is inert to every oxidising condition.

Identifiers

Formula
C4H10O
Functional group
Tertiary alcohols
Molar mass
74.12 g/mol
Also known as
tert-Butanol, tert-Butyl alcohol, 2-Methyl-2-propanol, t-Butanol, T-BUTYL ALCOHOL, 1,1-Dimethylethanol
Chemical identifiers
SMILES
CC(C)(C)O
InChI
InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
PubChem CID
6386

Properties

Melting Point
25.81 °C
Boiling Point
82.3 °C
Density
0.7886 g/cu cm at 20 °C
Water solubility
Miscible with water

Diagnostic tests

Alcohol oxidation comparison

Reagent
acidified potassium dichromate(VI)
Conditions
Compare equal test portions with propan-2-ol using gentle warming.
Positive observation
A green chromium(III) colour would indicate an oxidisable component.
Negative observation
The orange reagent remains orange for the tertiary-alcohol comparison.
Interpretation
The OH-bearing carbon lacks the hydrogen required for ordinary alcohol-to-carbonyl oxidation.
Scope
Expected negative for 2-methylpropan-2-ol under these conditions.
Limitations
Reference observation: unchanged colour.
Evidence
reference experiment

Related compounds

  • Alcohols

    A tertiary alcohol that contrasts with primary and secondary oxidation examples.

  • Tertiary alcohols

    A tertiary alcohol that contrasts with primary and secondary oxidation examples.

References

  1. PubChem Compound Summary: 2-Methylpropan-2-ol (CID 6386)National Center for Biotechnology Information · PubChem

    Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.

  2. OpenStax Organic Chemistry: Oxidation of alcoholsJohn McMurry · OpenStax · 2023

    Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.

  3. Hazardous Substances Data Bank (HSDB): 2-Methylpropan-2-ol — melting pointHazardous Substances Data Bank (HSDB)

    Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6386#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 94th Edition. CRC Press LLC, Boca Raton: FL 2013-2014, p. 3-392

  4. Hazardous Substances Data Bank (HSDB): 2-Methylpropan-2-ol — boiling pointHazardous Substances Data Bank (HSDB)

    Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6386#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 94th Edition. CRC Press LLC, Boca Raton: FL 2013-2014, p. 3-392

  5. Hazardous Substances Data Bank (HSDB): 2-Methylpropan-2-ol — densityHazardous Substances Data Bank (HSDB)

    Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6386#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 94th Edition. CRC Press LLC, Boca Raton: FL 2013-2014, p. 3-392

  6. ILO-WHO International Chemical Safety Cards (ICSCs): 2-Methylpropan-2-ol — solubilityILO-WHO International Chemical Safety Cards (ICSCs)

    Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6386#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.

  7. Alcohol detective: reference notesRoyal Society of Chemistry · RSC Education

    Source-supported qualitative reference observations.