6-cloro-1-hexeno - 6-cloro-1-hexeno

6-cloro-1-hexeno
6-cloro-1-hexeno.tif
6-cloro-1-hexeno-3D.gif
IUPAC name
6-chlorohex-1-eno
General
Other names 5-hexenyl
chloride 1-chloro-5-hexene
Semi-developed formula Cl CH 2 - (CH 2 ) 3 -CH = CH 2
Molecular formula C 6 H 11 Cl
Identifiers
CAS number 928-89-2[1]
ChemSpider 63418
PubChem 70233
Physical properties
Appearance liquid colorless
Density 896 kg/; 0,896 g/cm³
Molar mass 118.6 g / mol
Melting point −62 °C (211 K)
Boiling point 135 °C (408 K)
Vapor pressure 7,6 ± 0,2 mmHg
Refractive index (n D ) 1,438
Chemical properties
Solubility in water 125 mg / L
log P 3,15
Family Haloalkene
Dangerousness
Flash point 301 K (28 °C)
Related compounds
chloroalkenes 5-chloro-1-pentene
8-chloro-1-octene
cloroalcanos 1-clorohexano
chloroalkanes 6-chloro-1-hexyne
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 6-chloro-1-hexene , also called 6-clorohex-1-ene or 5-hexenyl chloride , is an organic compound of molecular formula C 6 H 11 Cl . It is a haloalkane linear six carbons with one atom of chlorine bonded to one of the terminal carbons and one double bond at the opposite end of the carbon chain . [ 2 ] [ 3 ] [ 4 ]

Physical and chemical properties

At room temperature , 6-chloro-1-hexene is a colorless liquid with a density lower than that of water, ρ = 0.896 g / cm³ . It has its boiling point at 135 ° C and its melting point at -62 ° C, the latter being an estimated value. [ 3 ]

The value of the logarithm of the partition coefficient , log P ≃ 3.15, it indicates that it is soluble in solvents apolar to polar solvents. Water solubility, very low, is approximately 125 mg / L . [ 3 ] It is incompatible with strong oxidizing agents . [ 4 ]

Synthesis

6-Chloro-1-hexene is prepared by treating a solution of 5-hexenol and anhydrous tetrachloromethane with triphenylphosphine , followed by refluxing with stirring for one hour. In this way, a yield of 71% is obtained . [ 5 ]

Applications

From 6-chloro-1-hexene 1,1,1,3-tetrachloroheptane can be prepared by chlorination with trichloromethanesulfonyl chloride; this reaction with a yield of 99% is reached, it takes place in alcohol , tert - butyl and requires a radical initiator . [ 6 ]

With this chloroalkene , coupling reactions , mediated by palladium and light, of four components have been achieved : the reaction takes place with alkyl iodides , alcohols and carbon monoxide , in the presence of dichlorobis (triphenylphosphine) palladium (II) under radiation of a xenon lamp , to obtain the corresponding functionalized esters . [ 7 ] [ 8 ] Moreover, the 6-chloro-1-hexene reacts with imines β-substituted in the presence of a catalyst of rhodiumto provide tri- and tetra-substituted imines. [ 9 ]

The reductive lithiation of 6-chloro-1-hexene is a versatile method for generating organolithium compounds . In this process, an excess of powdered lithium and a catalytic amount of 4,4′-di- tert- butylbiphenyl (DTBB) in tetrahydrofuran (THF) are used to give cyclopentanes ‌ in very high yields. [ 10 ]

See also

The following compounds are isomers of 6-chloro-1-hexene:

References

  1. CAS number
  2. 6-Chloro-1-hexene (PubChem)
  3. a b c 6-Chloro-1-hexene (ChemSpider)
  4. a b 6-Chloro-1-hexene (Chemical Book)
  5. Perfume composition (1990) Sawano, K .; Ishida, K .; Shimada, A. Patente US5141921A
  6. Wirth, T.; Singh, F.V. (2017). «35.1.5.1.12.7.1 Trichloromethylchlorination of Alkenes with Trichloromethanesulfonyl Chloride». Science of Synthesis Knowledge Updates 1: 435. Consultado el 25 de enero de 2020.
  7. Li, Y.; Xie, W.; Jiang, X. (2016). «1.2.7.1.4 Carbonylation Reactions». Science of Synthesis Knowledge Updates 2: 27. Consultado el 25 de enero de 2020.
  8. Fusano, A.; Ryu, I. (2014). «2.5.4.2 Reactions with Iodine Transfer». Science of Synthesis Knowledge Updates 2: 427. Consultado el 25 de enero de 2020.
  9. Colby, D.A.; Bergman, R.G.; Ellman, J.A. (2006). «Alkylation of α,β-Unsaturated Imines via C-H Bond Activation». Synfacts 8: 814. Consultado el 25 de enero de 2020.
  10. Lete, E.; Sotomayor, N (2011). «8.1.30.2.1.2 Arene-Catalyzed Lithiation». Science of Synthesis Knowledge Updates 4: 203. Consultado el 25 de enero de 2020.