3-Hexanol, 3-methyl- (597-96-6) Physical and Chemical Properties
3-Hexanol, 3-methyl-
A branched tertiary aliphatic alcohol (3‑methylhexan‑3‑ol) used as a solvent and intermediate in specialty chemical synthesis, formulation development, and analytical standards for R&D and QC.
| CAS Number | 597-96-6 |
| Family | Tertiary aliphatic alcohols |
| Typical Form | Colorless liquid |
| Common Grades | EP |
3-Hexanol, 3-methyl- is a branched tertiary alcohol of the alkane-derived alcohol family; the preferred IUPAC name is 3-methylhexan-3-ol. The molecule contains a central quaternary (tertiary alcohol-bearing) carbon at C-3 bonded to an \(\mathrm{OH}\) group and three carbon substituents (two alkyl chains and one methyl), giving the substance significant steric hindrance around the hydroxyl function. The formula is \(\mathrm{C}7\mathrm{H}\) and one hydrogen-bond donor and one acceptor site; these features produce modest polarity compared with primary and secondary alcohols of similar carbon count.}\mathrm{O}\) and the molecular weight is \(\mathrm{116.20}\,\mathrm{g}\,\mathrm{mol}^{-1}\). Electronic polarity is dominated by a single aliphatic hydroxyl group with a topological polar surface area of \(\mathrm{20.2
As a tertiary alcohol, 3-methylhexan-3-ol is less prone to oxidation under mild conditions than primary or secondary alcohols but can undergo acid-catalyzed dehydration to give branched alkenes. The moderate calculated lipophilicity (XLogP \(\,=1.9\)) and low TPSA favor solubility in nonpolar and moderately polar organic solvents while limiting water solubility relative to lower molecular-weight alcohols. Steric shielding around the hydroxyl reduces intermolecular hydrogen-bonding relative to less hindered alcohols, which affects volatility, solvation, and reactivity in condensation or esterification reactions.
Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
No experimentally established value for this property is available in the current data context.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
The molecule presents a single hydroxyl functionality on a seven‑carbon framework, producing limited hydrogen-bonding capacity (one donor, one acceptor) and a calculated XLogP of 1.9. These descriptors indicate low-to-moderate aqueous solubility with good miscibility in common organic solvents (aliphatic hydrocarbons, ethers, esters, ketones). The low topological polar surface area (\(\mathrm{20.2}\)) and bulky branching reduce hydration enthalpy relative to linear alcohols, so partitioning into nonpolar phases is favored. No quantitative solubility data are available in the current data context.
Reactivity and Stability
3-Methylhexan-3-ol is a tertiary alcohol: it is comparatively resistant to oxidation to carbonyl compounds by mild oxidants but can undergo dehydration under strong acid catalysis to yield branched olefins. The hydroxyl-bearing tertiary center is sterically hindered, lowering nucleophilic substitution at that carbon; esterification and other substitution reactions typically require forcing conditions or activated reagents.
Notably, entries for this substance indicate peroxide formation can occur on concentration (e.g., during distillation/evaporation), with at least one sample reported to develop measurable peroxide content over storage. Concentration and prolonged storage can therefore increase peroxide risk; appropriate testing and mitigation are recommended prior to operations that remove solvent or otherwise concentrate the material. The substance has a GHS-associated acute oral hazard classification (see Safety section).
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: \(\mathrm{C}7\mathrm{H}\) }\mathrm{O
- Molecular weight: \(\mathrm{116.20}\,\mathrm{g}\,\mathrm{mol}^{-1}\)
- Exact / monoisotopic mass: \(\mathrm{116.120115130}\) (as reported)
LogP and Polarity
- XLogP3 (calculated): 1.9
- Topological polar surface area (TPSA): 20.2
- Hydrogen-bond donor count: 1
- Hydrogen-bond acceptor count: 1
- Rotatable bond count: 3
These computed descriptors indicate moderate lipophilicity and limited polar surface area, consistent with a branched tertiary alcohol that favors organic phases over aqueous.
Structural Features
- IUPAC name: 3-methylhexan-3-ol
- SMILES: CCCC(C)(CC)O
- InChI: InChI=1S/C7H16O/c1-4-6-7(3,8)5-2/h8H,4-6H2,1-3H3
- InChIKey: KYWJZCSJMOILIZ-UHFFFAOYSA-N
Structurally, the hydroxyl is attached to a tertiary carbon (C-3) that bears three alkyl substituents (two ethyl-like chains and one methyl). The branching increases steric hindrance around the \(\mathrm{OH}\) group, diminishing intermolecular hydrogen bonding and reactivity at that center relative to less hindered alcohols. The combination of branching and limited polar surface area leads to lowered aqueous miscibility and altered volatility compared with linear hexanols.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS: 597-96-6
- Deprecated CAS: 111768-07-1
- EC number: 209-910-4
- UNII: 6YG8Q4JZ7B
- DSSTox Substance ID: DTXSID90870658
- Nikkaji Number: J49.424K
- NSC Number: 27229
- InChI: InChI=1S/C7H16O/c1-4-6-7(3,8)5-2/h8H,4-6H2,1-3H3
- InChIKey: KYWJZCSJMOILIZ-UHFFFAOYSA-N
- SMILES: CCCC(C)(CC)O
(Values listed appear in provided compound descriptors and identifier lists.)
Synonyms and Structural Names
Common synonyms recorded for this substance include: 3-methylhexan-3-ol; 3-methyl-3-hexanol; 3-hexanol, 3-methyl-; 2-ethyl-2-pentanol; (+/−)-3-methyl-3-hexanol. Other depositor-supplied synonyms and registry tags exist in supplier and database listings; the principal chemical names above describe the same connectivity and stereochemical ambiguity (racemic/undefined stereocenter).
Industrial and Commercial Applications
Representative Uses and Industry Sectors
No concise application summary is available in the current data context; in practice this substance is selected based on its general properties described above. Because it is a branched tertiary alcohol with moderate lipophilicity and limited polarity, typical class-level uses for similar compounds include roles as organic solvents, intermediates in organic synthesis, or components in formulations where low volatility and branched-alcohol properties are desired. Commercial grade reported: EP.
Role in Synthesis or Formulations
No concise application summary is available in the current data context; in practice the substance may be used as a building block or solvent in specialty chemical synthesis where a hindered tertiary alcohol is required, or as a minor component in formulations exploiting the alcohol's solvent or solvency-modifying behavior.
Safety and Handling Overview
Acute and Occupational Toxicity
Available hazard coding indicates an acute oral toxicity hazard with the statement code H302 (harmful if swallowed) and an aggregated classification consistent with acute oral toxicity category 4. Occupational exposure controls should follow standard practices for organic liquids: minimize inhalation and dermal contact, use local exhaust ventilation where vapors may accumulate, and implement exposure monitoring when appropriate.
When concentrated (e.g., during distillation or prolonged storage), peroxide formation has been reported for this substance; peroxide-containing residues can present shock- or heat-sensitive hazards. Test for peroxides prior to concentration operations and implement peroxide mitigation strategies as required.
Storage and Handling Considerations
General precautions for handling a branched aliphatic alcohol apply: store in a cool, well-ventilated area away from strong oxidizers and strong acids. Avoid prolonged storage in partially filled containers that may concentrate peroxides; if concentration or distillation is performed, carry out appropriate peroxide testing and employ inert-atmosphere and explosion‑proof equipment as needed. Use chemical-resistant gloves, safety glasses, and appropriate engineering controls to prevent inhalation and skin contact. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and applicable local legislation.
