4-Octyne
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| Names | |
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| Preferred IUPAC name
Oct-4-yne | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.016.119 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C8H14 | |
| Molar mass | 110.200 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.751 g/mL |
| Melting point | −103 °C (−153 °F; 170 K) |
| Boiling point | 131–132 °C (268–270 °F; 404–405 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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4-Octyne, also known as dipropylethyne, is a type of alkyne with a triple bond at its fourth carbon (the '4-' indicates the location of the triple bond in the chain). Its formula is C8H14.
4-Octyne forms with 5-decyne, 3-hexyne, and 2-butyne a group of symmetric alkynes.
Preparation
One method for synthesizing 4-octyne is the reaction between acetylene and two equivalents of 1-bromopropane. Acetylene is first deprotonated by a base to give an anion, which then undergoes nucleophilic substitution with the bromopropane. The resulting alkyne is again deprotonated and reacts similarly with a second molecule of bromopropane. This reaction can be carried out in liquid ammonia at −70 °C with sodium amide as the base.[1]
Another synthetic route is the elimination reaction of 4,5-dibromooctane, which can be done in similar conditions.[2]
Properties
4-octyne is a colorless liquid at room temperature. Its density at 25 °C and otherwise stable conditions is 0.751 g/mL. The boiling point is 131–132 °C. The average molar mass is 110.20 g/mol.[3]
References
- ^ Seifert, H. (1948-05-01). "Olefinsynthesen in der C6- bis C11-Reihe". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften (in German). 79 (3): 198–215. doi:10.1007/BF00899394. ISSN 1434-4475.
- ^ Miller, Harold N.; Greenlee, Kenneth W.; Derfer, John M.; Boord, Cecil E. (1954). "Mono- and Di-Alkylacetylenes from Vicinal Dihalides and Sodium Amide in Liquid Ammonia1". The Journal of Organic Chemistry. 19 (12): 1882–1888. doi:10.1021/jo01377a003. ISSN 0022-3263.
- ^ Lide, David R. (2010). "Physical Constants of Organic Compounds". CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, FL: CRC Press/Taylor and Francis. pp. 3–406.
External links
- Sigma-Aldrich Co., 4-Octyne. Retrieved on 16 August 2016.