tert-Amyl alcohol

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tert-Amyl alcohol
Stereo, skeletal formula of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Names
Preferred IUPAC name
2-Methyl-2-butanol[1]
Systematic IUPAC name
2-Methylbutan-2-ol[1]
Other names
tert-Amyl alcohol, t-Amylol, TAA[1]

tert-Pentyl alcohol, 2-methyl-2-butyl alcohol, t-Pentylol,[1]
Amylene hydrate[1]

Dimethylethylcarbinol[1]
Identifiers
75-85-4 YesY
1361351
ChEMBL ChEMBL44658 YesY
ChemSpider 6165 YesY
EC Number 200-908-9
Jmol 3D model Interactive image
KEGG D02931 YesY
MeSH tert-amyl+alcohol
PubChem 6405
RTECS number SC0175000
UNII 69C393R11Z YesY
UN number 1105
  • InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 YesY
    Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N YesY
  • CCC(C)(C)O
Properties
C5H12O
Molar mass 88.15 g·mol−1
Appearance Colorless liquid
Odor Camphorous
Density 0.805 g/cm^3−3 [2]
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)
1.405
Viscosity 4.4740 mPa·s (at 298.15 K)[2]
Thermochemistry
229.3 J K−1 mol−1
−380.0–−379.0 kJ mol−1
−3.3036–−3.3026 MJ mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

tert-Amyl alcohol (TAA), systematic name: 2-methyl-2-butanol (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 which is miscibile with both water and organic solvents. Although it can be produced naturally, by the fermentation of ethanol, it is primarily produced synthetically via hydroformylation.

Production

Industrial

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.[3][4]

Natural occurrence

Fusel alcohols including TAA are grain fermentation by-products and therefore trace amounts of TAA are present in many alcoholic beverages.[5] Trace levels of TAA have also been detected in various foodstuffs, including fried bacon, cassava,[6][7] rooibos tea[8] and fruits such as apple and pineapple.

Pharmacology

Between about 1880–1950, 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.[4]

Oxidation of TAA to 2-methyl-2,3-butanediol

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.[9] 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.[10] It is active in doses of 2,000–4,000 mg, making it 20 times more potent than ethanol.[11][12] Its hypnotic potency is between chloral hydrate and paraldehyde[13] and between benzodiazepines and ethanol.

In rats, TAA is primarily metabolized via glucuronidation, as well as by oxidation to 2-methyl-2,3-butanediol. It is likely that the same path is followed in humans,[14] though older sources suggest it is excreted unchanged.[4]

Overdose and toxicity

An overdose produces symptoms similar to alcohol poisoning and is a medical emergency due to the sedative/depressant properties and relatively high potency of the drug. The oral LD50 in rats is 1000 mg/kg. The subcutaneous LD50 in mice is 2100 mg/kg.[15]

See also

References

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  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V2: 716. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
  4. ↑ 4.0 4.1 4.2 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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