4-Octyne

Names
Preferred IUPAC name

Oct-4-yne

Other names

* Dipropylacetylene
* 1,2-Dipropylacetylene
* Dipropylethyne

Identifiers

CAS Number

* 1942-45-6 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 15221

EC Number |

* 217-730-2

PubChem CID

* 16029

UNII |

* IJI0Q2V1Z6 Y

InChI

* InChI=1S/C8H14/c1-3-5-7-8-6-4-2/h3-6H2,1-2H3

Key: GZTNBKQTTZSQNS-UHFFFAOYSA-N

* InChI=1/C8H14/c1-3-5-7-8-6-4-2/h3-6H2,1-2H3

Key: GZTNBKQTTZSQNS-UHFFFAOYAB

SMILES

* CCCC#CCCC

Properties

Chemical formula

| 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).

Infobox references

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Preparation
* 2 Properties
* 3 References
* 4 External links

## 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

1. ↑ Seifert, H. (1948-05-01). "Olefinsynthesen in der C6- bis C11-Reihe" (in de). Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 79 (3): 198–215. doi:10.1007/BF00899394. ISSN 1434-4475. https://doi.org/10.1007/BF00899394.
2. ↑ 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" (in en). The Journal of Organic Chemistry 19 (12): 1882–1888. doi:10.1021/jo01377a003. ISSN 0022-3263. https://pubs.acs.org/doi/abs/10.1021/jo01377a003.
3. ↑ 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.

* v
* t
* e

Alkynes

* Ethyne ( C2H2 )
* Propyne ( C3H4 )
* Butyne ( C4H6 )
* 1
* 2
* Pentyne ( C5H8 )
* 1
* 2
* Hexyne ( C6H10 )
* Heptyne ( C7H12 )
* Octyne ( C8H14 )
* 2
* 4
* Nonyne ( C9H16 )
* Decyne ( C10H18 )
* 1
* 5

Preparations|

* Cracking
* [[Chemistry:DehydrogenatDehydrogenation]] of alkane]], alkene
* Alkylation of alkynyl anion
* Dehydrohalogenation of dihaloalkane
* Fritsch–Buttenberg–Wiechell rearrangement
* Corey–Fuchs reaction
* Seyferth–Gilbert homologation

Reactions|

* Deprotonation
* Hydrogenation
* Halogenation
* Hydration
* Hydroboration
* Hydrohalogenation
* Thiol-yne reaction
* Alkyne trimerisation
* Diels–Alder reaction
* Pauson–Khand reaction
* Azide-alkyne Huisgen cycloaddition
* Sonogashira coupling
* Cadiot–Chodkiewicz coupling
* Glaser coupling
* Favorskii reaction

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