2-Methylbut-3-yn-2-ol

2-Methylbut-3-yn-2-ol
Names
	Other names Ethynylmethylcarbinol; Dimethylethynylcarbinol; 1,1-Dimethyl-2-propyn-1-ol; Dimethylethynylmethanol; MB;
Identifiers
CAS Number	115-19-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3185871;
ChemSpider	21106133;
ECHA InfoCard	100.003.700
EC Number	204-070-5;
PubChem CID	8258;
RTECS number	ES0810000;
UNII	EHB904XHKH;
UN number	1987
CompTox Dashboard (EPA)	DTXSID2021949 ;
	InChI InChI=1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3 Key: CEBKHWWANWSNTI-UHFFFAOYSA-N;
	SMILES CC(C)(C#C)O;
Properties
Chemical formula	C5H8O
Molar mass	84.118 g·mol−1
Appearance	Colorless liquid
Density	0.8637 g/cm3
Melting point	3 °C (37 °F; 276 K)
Boiling point	104 °C (219 °F; 377 K)
Solubility in water	good
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H226, H302, H315, H318, H319, H335, H361
GHS precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P303+361+353, P304+340, P305+351+338, P308+313, P310, P312, P321, P330, P332+313
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).
	Infobox references

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] 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.[3]

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.

References

Donald D. Coffman (1940). "Dimethylethynylcarbinol". Org. Synth. 20: 40. doi:10.15227/orgsyn.020.0040.
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: 1806-1807. doi:10.1021/ja993838z.
Eberhard Breitmaier (2006). Terpenes: Flavors, Fragrances, Pharmaca, Pheromones. Wiley-VCH. doi:10.1002/9783527609949. ISBN 9783527609949.
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.

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[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: 1806-1807. doi:10.1021/ja993838z.

[book-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.