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2-Methylbut-3-yn-2-ol

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2-Methylbut-3-yn-2-ol
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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.700 Edit this at Wikidata
EC Number
  • 204-070-5
PubChem CID
RTECS number
  • ES0810000
UNII
UN number 1987
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3Key: CEBKHWWANWSNTI-UHFFFAOYSA-N
SMILES
  • CC(C)(C#C)O
Properties
Chemical formula C5H8O
Molar mass 84.118 g·mol
Appearance Colorless liquid
Density 0.8637 g/cm
Melting point 3 °C (37 °F; 276 K)
Boiling point 104 °C (219 °F; 377 K)
Solubility in water good
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H225, H226, H302, H315, H318, H319, H335, H361
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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 (Favorskii reaction) or with Lewis acid catalysts. 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.

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:

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

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

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.
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