Tert-Amyl alcohol

tert-Amyl alcohol
Stereo, skeletal formula of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Names
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)
1361351
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.827 Edit this at Wikidata
EC Number
  • 200-908-9
KEGG
MeSH tert-amyl+alcohol
RTECS number
  • SC0175000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 checkY
    Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N checkY
  • CCC(C)(C)O
Properties
C5H12O
Molar mass 88.150 g·mol−1
Appearance Colorless liquid
Odor Camphorous
Density 0.805 g/cm3[1]
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[2]
log P 1.0950.5:1 volume ratio
Vapor pressure 1.6 kPa (at 20 °C)
−7.09×10−5 cm3/mol
1.405
Viscosity 4.4740 mPa·s (at 298.15 K)[1]
Thermochemistry
229.3 J K−1 mol−1
−380.0 to −379.0 kJ mol−1
−3.3036 to −3.3026 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H315, H332, H335
P210, P261
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
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).
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tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

Historically, TAA has been used as an anesthetic[3] and more recently as a recreational drug.[4] TAA is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol.[5] 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.[6]

TAA is a colorless liquid with a burning flavor[7] and an unpleasant odor[8] similar to paraldehyde with a hint of camphor.[9] TAA remains liquid at room temperature, making it a useful alternative solvent to tert-butyl alcohol.

  1. ^ a b Lomte, S.B.; Bawa, M.J.; Lande, M.K.; Arbad, B.R. (2009). "Densities and Viscosities of Binary Liquid Mixtures of 2-Butanone with Branched Alcohols at (293.15 to 313.15) K". Journal of Chemical & Engineering Data. 54: 127–130. doi:10.1021/je800571y.
  2. ^ Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2014). "Section 3 - Physical Constants of Organic Compounds". CRC Handbook of Chemistry and Physics, 95th Edition (95th ed.). CRC Press. p. 362. ISBN 9781482208689. OCLC 908078665.
  3. ^ Cite error: The named reference adriani was invoked but never defined (see the help page).
  4. ^ Rusiecka, Izabela; Gągało, Iwona; Anand, Jacek Sein; Schetz, Daria; Waldman, Wojciech (October 2016). "Drinking "Vodka" or vodka – This is a question". Toxicology in Vitro. 36: 66–70. doi:10.1016/j.tiv.2016.07.009. ISSN 1879-3177. PMID 27448500.
  5. ^ Martin, J (2004). "Influence of oxygenated fuel additives and their metabolites on γ-aminobutyric acidA (GABAA) receptor function in rat brain synaptoneurosomes". Toxicology Letters. 147 (3): 209–217. doi:10.1016/j.toxlet.2003.10.024. PMID 15104112.
  6. ^ Syed, Alia N.; Leo, Raphael J. (2022-11-22). "Recreational 2-Methyl-2-Butanol Use: An Emerging Wave of Misuse of an Ethanol Substitute on the Horizon?". The Primary Care Companion for CNS Disorders. 24 (6): 44189. doi:10.4088/PCC.22cr03292. ISSN 2155-7780. PMID 36441984. S2CID 253700629.
  7. ^ O'Neil, Maryadele J., ed. (2006). The Merck index (14th ed.). Merck. p. 1232. ISBN 9780911910001. OCLC 70882070.
  8. ^ Cite error: The named reference :5 was invoked but never defined (see the help page).
  9. ^ Yandell, D. W.; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. 5: 88–98.