|Density||962 kg/m³; 0,962 g/cm³|
|Molar mass||116.59 g / mol|
|Melting point||−34 °C (239 K)|
|Boiling point||153 °C (426 K)|
|Vapor pressure||5,9 ± 0,3 mmHg|
|Refractive index (n D )||1,451|
|Solubility in water||445 mg / L|
|Flash point||310 K (37 °C)|
|chloroalkanes|| 5-chloro-1-pentino |
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
The 6-chloro-1-hexyne , also called 6-clorohex-1-yne , 5-hexinocloruro and chloride of 5-hexynyl , is an organic compound of molecular formula C 6 H 9 Cl . It is a linear chloroalkyne six carbons with one atom of chlorine bonded to one of the terminal carbons and one triple bond at the opposite end of the carbon chain . [ 2 ] [ 3 ] [ 4 ]
Physical and chemical properties
At room temperature , 6-chloro-1-hexyne is a yellow liquid with a density lower than that of water, ρ = 0.962 g / cm³ . It has its boiling point at 153 ° C and its melting point at -34 ° C, the latter being an estimated value. [ 3 ]
The value of the logarithm of its partition coefficient , log P ≃ 2.35, indicates that it is more soluble in nonpolar solvents than in polar solvents. In water , its solubility is approximately 445 mg / L. [ 3 ] Regarding its reactivity , it is incompatible with strong oxidizing agents . [ 5 ]
6-Chloro-1-hexyne has been used in the alkylation of secondary amines - such as dimethylamine - to form the corresponding tertiary amine. The reaction is carried out in benzene at 80 ° C for 13 hours, achieving a yield of 60%. [ 8 ]
Hydroboration of 6-chloro-1-hexyne with dialkylborans and in situ transmetalation with diethylzinc have been studied ; if an addition to an aldehyde follows , the corresponding allyl alcohol is obtained , this reaction being enantioselective . [ 9 ] Similarly, the addition of various bromoalkanes to 6-chloro-1-hexyne allows the preparation of longer chain alkynes ; in this case, a mixture of bis (η 3 -alyl) dichlorodipaladium (II) and copper (I) iodide is used as the catalyst . [ 10]
This chloroalkine is involved in the synthesis of indole derivatives used as antibacterial agents against Staphylococcus aureus . [ 11 ] Also in the production of conjugated Z-alken-yn-yl acetates, such as Z-13-hexadecen-11-yl acetate, a component of the sex pheromone of the processionary moth. pine . [ 12 ]
6-chloro-1-hexyne is a compound flammable whose flash point is 37 ° C. When burning, it releases toxic products such as carbon monoxide and hydrochloric acid . Its vapors can form explosive mixtures with air. On the other hand, contact with this substance causes irritation to the skin and eyes. [ 5 ]
- CAS number
- 6-Chloro-1-hexyne (PubChem)
- 6-Chloro-1-hexyne (ChemSpider)
- 6-Chloro-1-hexyne (Chemical Book)
- 6-Chloro-1-hexyne. MSDS (Thermo Fisher)
- 6-Chloro-1-hexyne (ChemSrc)
- Taylor, W.R.; Strong, F.M. (1950). «Synthesis of Unsaturated Fatty Acids». J. Am. Chem. Soc. 72 (9): 4263-4265. Consultado el 13 de febrero de 2020.
- Lawrence, S.A. (2009). «220.127.116.11.4.3.2 Method 2: Reactions of Primary, Secondary, or Tertiary Amines with Alkyl Halides». Science of Synthesis 40: 526. Consultado el 2 de enero de 2019.
- Kauffman, M. C.; Walsh, P. J (2011). «18.104.22.168.1 Alkenylation with Organozinc Reagents through Hydroboration–Transmetalation of Alkynes». Science of Synthesis: Stereoselective Synthesis 2: 475. Consultado el 13 de febrero de 2020.
- Aitken, RA; Aitken, K. (2008). "22.214.171.124.7.2 Variation 2: With a Bromoalkane" . Science of Synthesis 43 : 601 . Retrieved February 13, 2020 .
- Lenin, H.H., Lauro, F.V., Marcela, R.N. et al. (2017). «Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus». Journal of Chemical Biology 10 (4): 159-177. Consultado el 13 de febrero de 2020.
- Method for producing a conjugated Z-alken-yn-yl acetate (2014) Yamashita, M.; Fukumoto, T.; Kinsho, T. Patente US9376368B2