2-Methylbut-3-yn-2-ol

Last updated
2-Methylbut-3-yn-2-ol
Me2(HO)CC2H.png
Names
Preferred IUPAC name
2-Methylbut-3-yn-2-ol
Other names
  • Ethynylmethylcarbinol
  • Dimethylethynylcarbinol
  • 1,1-Dimethyl-2-propyn-1-ol
  • Dimethylethynylmethanol
  • MB
  • Mebynol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.700 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-070-5
PubChem CID
RTECS number
  • ES0810000
UNII
UN number 1987
  • InChI=1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3
    Key: CEBKHWWANWSNTI-UHFFFAOYSA-N
  • CC(C)(C#C)O
Properties
C5H8O
Molar mass 84.118 g·mol−1
AppearanceColorless liquid
Density 0.8637 g/cm3
Melting point 3 °C (37 °F; 276 K)
Boiling point 104 °C (219 °F; 377 K)
good
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H226, H302, H315, H318, H319, H335, H361
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 20 °C (68 °F; 293 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Methylbut-3-yn-2-ol is the organic compound with the formula HC2C(OH)Me2 (Me = CH3). A colorless liquid, it is classified as an alkynyl alcohol.

Preparation and use

It arises from the condensation of acetylene and acetone. The addition can be promoted with base [1] (Favorskii reaction) or with Lewis acid catalysts. [2] 2-Methylbut-3-yn-2-ol is produced on an industrial scale as a precursor to terpenes and terpenoids.

2-Methylbut-3-yn-2-ol is an intermediate in this industrial route to geraniol. IndustrialRouteGeranylAlc.png
2-Methylbut-3-yn-2-ol is an intermediate in this industrial route to geraniol.

2-Methylbut-3-yn-2-ol also is used as a monoprotected version of acetylene. For example, after arylation at carbon, the acetone can be removed with base: [4]

HC2C(OH)Me2 + ArX + base → ArC2C(OH)Me2 + [Hbase]X
ArC2C(OH)Me2 → ArC2H + OCMe2

In this regard, 2-methylbut-3-yn-2-ol is used similarly to trimethylsilylacetylene.

Related Research Articles

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Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

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<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

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2
CH
3
. It is a white solid that is soluble in 1,2-dimethoxyethane, and tetrahydrofuran. To preclude its degradation by oxygen and water, propynyllithium and its solutions are handled under inert gas. Although commonly depicted as a monomer, propynyllithium adopts a more complicated cluster structure as seen for many other organolithium compounds.

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References

  1. Donald D. Coffman (1940). "Dimethylethynylcarbinol". Org. Synth. 20: 40. doi:10.15227/orgsyn.020.0040.
  2. Frantz, Doug E.; Fässler, Roger; Carreira, Erick M. (2000). "Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes". J. Am. Chem. Soc. 122 (8): 1806–1807. doi:10.1021/ja993838z.
  3. Eberhard Breitmaier (2006). Terpenes: Flavors, Fragrances, Pharmaca, Pheromones. Wiley-VCH. doi:10.1002/9783527609949. ISBN   9783527609949.
  4. Gordon, John (2001). "2-Methylbut-3-yn-2-ol". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–2. doi:10.1002/047084289X.rm157. ISBN   0471936235.