tert-Amyl alcohol
tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.
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| Names | |||
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| Preferred IUPAC name
2-Methylbutan-2-ol | |||
| Other names
2-Methyl-2-butanol tert-Amyl alcohol t-Amylol TAA tert-Pentyl alcohol 2-Methyl-2-butyl alcohol t-Pentylol Amylene hydrate Dimethylethylcarbinol | |||
| Identifiers | |||
3D model (JSmol) |
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| 1361351 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.827 | ||
| EC Number |
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| KEGG | |||
| MeSH | tert-amyl+alcohol | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 1105 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C5H12O | |||
| Molar mass | 88.150 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Camphorous | ||
| Density | 0.805 g/cm3 | ||
| Melting point | −9 °C; 16 °F; 264 K | ||
| Boiling point | 101 to 103 °C; 214 to 217 °F; 374 to 376 K | ||
| 120 g·dm−3 | |||
| Solubility | soluble in water, benzene, chloroform, diethylether and ethanol | ||
| log P | 1.0950.5:1 volume ratio | ||
| Vapor pressure | 1.6 kPa (at 20 °C) | ||
| −7.09×10−5 cm3/mol | |||
Refractive index (nD) |
1.405 | ||
| Viscosity | 4.4740 mPa·s (at 298.15 K) | ||
| Thermochemistry | |||
Std molar entropy (S⦵298) |
229.3 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) |
−380.0 to −379.0 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) |
−3.3036 to −3.3026 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
| Danger | |||
| H225, H315, H332, H335 | |||
| P210, P261 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 19 °C (66 °F; 292 K) | ||
| 437 °C (819 °F; 710 K) | |||
| Explosive limits | 9% | ||
| Safety data sheet (SDS) | hazard.com | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |||
Historically, TAA has been used as an anesthetic and more recently as a recreational drug. TAA is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol. The psychotropic effects of TAA and ethanol are similar, though distinct. Impact on coordination and balance are proportionately more prominent with TAA, which is significantly more potent by weight than ethanol. Its appeal as an alternative to ethanol may stem from its lack of a hangover (due to different metabolic pathways) and the fact that it is often not detected on standard drug test.
TAA is a colorless liquid with a burning flavor and an unpleasant odor similar to paraldehyde with a hint of camphor. TAA remains liquid at room temperature, making it a useful alternative solvent to tert-butyl alcohol.