2M2B
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| Names | |||
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Preferred IUPAC name
2-Methylbutan-2-ol
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| 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 |
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| Identifiers | |||
75-85-4 
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| 3D model (Jmol) | Interactive image | ||
| 1361351 | |||
| ChEBI | CHEBI:132750 | ||
| ChEMBL |
ChEMBL44658
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| ChemSpider |
6165
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| ECHA InfoCard | 100.000.827 | ||
| EC Number | 200-908-9 | ||
| KEGG |
D02931
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| MeSH | tert-amyl+alcohol | ||
| PubChem | 6405 | ||
| RTECS number | SC0175000 | ||
| UNII |
69C393R11Z
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| UN number | 1105 | ||
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| Properties | |||
| C5H12O | |||
| Molar mass | 88.15 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Camphorous | ||
| Density | 0.805 g/cm−3 | ||
| 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 | |||
| log P | 1.095 | ||
| Vapor pressure | 1.6 kPa (at 20 °C) | ||
| -70.9·10−6 cm3/mol | |||
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Refractive index (nD)
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1.405 | ||
| Viscosity | 4.4740 mPa·s (at 298.15 K) | ||
| Thermochemistry | |||
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Std molar
entropy (S |
229.3 J K−1 mol−1 | ||
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Std enthalpy of
formation (ΔfH |
−380.0–−379.0 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−3.3036–−3.3026 MJ mol−1 | ||
| Hazards | |||
| Safety data sheet | hazard.com | ||
| GHS pictograms |
 
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| GHS signal word | DANGER | ||
| H225, H315, H332, H335 | |||
| P210, P261 | |||
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EU classification (DSD)
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 F  Xn
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| R-phrases | R11, R20, R37/38 | ||
| S-phrases | (S2), S46 | ||
| NFPA 704 | |||
| Flash point | 19 °C (66 °F; 292 K) | ||
| 437 °C (819 °F; 710 K) | |||
| Explosive limits | 9% | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| Infobox references | |||
tert-Amyl alcohol (TAA), systematic name: 2-methylbutan-2-ol (2M2B), is a branched pentanol used primarily as a pharmaceutical or pigment solvent. It remains liquid at room temperature making it a useful alternative to tert-butyl alcohol. It is a colorless liquid with a pungent odor of camphor. It is slightly soluble in water and miscibile organic solvents. Although it can be produced naturally, by the fermentation of ethanol, it is primarily produced synthetically via hydroformylation.
Like other oxo alcohols TAA is primarily produced via hydroformylation. The reaction of 2-methyl-2-butene with water in the presence of an acid catalyst yields TAA.
Fusel alcohols including TAA are grain fermentation by-products and therefore trace amounts of TAA are present in many alcoholic beverages. Trace levels of TAA have also been detected in various foodstuffs, including fried bacon, cassava,rooibos tea and fruits such as apple and pineapple.
Between about 1880 and 1950, it was used as an anesthetic, with the contemporary name of amylene hydrate. It was mainly used as a solvent for tribromoethanol, forming "avertin fluid" at a 0.5 : 1 ratio of TAA to TBE. TAA was rarely used as a sole hypnotic because of the existence of more efficient drugs.
Tertiary alcohols like TAA cannot be oxidised to aldehyde or carboxylic acid metabolites, which are often toxic; this makes them safer drugs than primary alcohols. However, like other tertiary alcohol based anaesthetics (e.g. methylpentynol, ethchlorvynol) TAA was eventually superseded by safer and more effective agents.
TAA produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation. It is active in doses of 2,000–4,000 mg, making it 20 times more potent than ethanol. Its hypnotic potency is between chloral hydrate and paraldehyde and between benzodiazepines and ethanol.
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Wikipedia