1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is HC2C4H9. A colorless liquid, it is one of three isomers of hexyne.[1] It is used as a reagent in organic synthesis.
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| Names | |
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| Preferred IUPAC name
Hex-1-yne | |
| Other names
n-Butylacetylene
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.010.671 |
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CompTox Dashboard (EPA)
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| Properties | |
| C6H10 | |
| Molar mass | 82.146 g·mol−1 |
| Appearance | colorless liquid (impure samples can appear yellowish) |
| Density | 0.72 g/cm3 |
| Melting point | −132 °C (−206 °F; 141 K) |
| Boiling point | 71 to 72 °C (160 to 162 °F; 344 to 345 K) |
| 0.36 g/L | |
| Hazards | |
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Main hazards
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Irritant, Flammable, Health Hazard |
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| Danger | |
| H225, H304, H315, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301 P310, P302 P352, P303 P361 P353, P304 P340, P305 P351 P338, P312, P321, P331, P332 P313, P337 P313, P362, P370 P378, P403 P233, P403 P235, P405, P501 | |
| Flash point | −20 °C (−4 °F; 253 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
edit1-Hexyne can be prepared by the reaction of monosodium acetylide with butyl bromide:[1]
- NaC2H BrC4H9 → HC2C4H9 NaBr
Its reactivity illustrates the behavior of terminal alkylacetylenes. The hexyl derivative is common test substrate because it is conveniently volatile. It undergoes deprotonation at C-3 and C-1 with butyl lithium:
- HC2C4H9 2 BuLi → LiC2CH(Li)C3H7 2 BuH
This reaction allows alkylation at the 3-position.[2]
Catechol borane adds to 1-hexyne to give the 1-hexenyl borane. [3]
1-Hexyne reacts with diethyl fumarate to produce n-hexylsuccinic acid.[4]
See also
editReferences
edit- ^ a b Kenneth N. Campbell, Barbara K. Campbell (1950). "n-Butylacetylene". Organic Syntheses. 30: 15. doi:10.15227/orgsyn.030.0015.
- ^ A. J. Quillinan, F. Scheinmann (1978). "3-Alkyl-1-Alkynes Synthesis: 3-Ethyl-1-Hexyne". Organic Syntheses. 58: 1. doi:10.15227/orgsyn.058.0001.
- ^ Norio Miyaura Akira Suzuki (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene". Organic Syntheses. 68: 130. doi:10.15227/orgsyn.068.0130.
- ^ Hogsed, M. J.; Lindsey, R. V. (1953-10-01). "The Reaction of 1-Hexyne and Diethyl Fumarate". Journal of the American Chemical Society. 75 (19): 4846–4847. doi:10.1021/ja01115a517. ISSN 0002-7863.