1-Hexyne

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.

1-Hexyne
Names
Preferred IUPAC name
Hex-1-yne
Other names
n-Butylacetylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.671
EC Number
  • 211-736-9
UNII
  • InChI=1S/C6H10/c1-3-5-6-4-2/h1H,4-6H2,2H3
    Key: CGHIBGNXEGJPQZ-UHFFFAOYSA-N
  • CCCCC#C
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
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant, Flammable, Health Hazard
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
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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Infobox references

Synthesis and reactions

1-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

References
  1. Kenneth N. Campbell, Barbara K. Campbell (1950). "n-Butylacetylene". Organic Syntheses. 30: 15. doi:10.15227/orgsyn.030.0015.
  2. 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.
  3. 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.
  4. 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.
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