4-chloro-1-butino - 4-cloro-1-butino

4-chloro-1-butino
4-chloro-1-butyne.tif
4-chloro-1-butino-3D.gif
IUPAC name
4-clorobut-1-ino
General
Semi-developed formula ClCH2-CH2-C≡C
Molecular formula C4H5Cl
Identifiers
CAS number 51908-64-6[1]
ChemSpider 36711
PubChem 40173
Physical properties
Appearance liquid colorless
Density 986 kg/; 0,986 g/cm³
Molar mass 88.53 g / mol
Melting point −59 °C (214 K)
Boiling point 96 °C (369 K)
Vapor pressure 49,6 ± 0,2 mmHg
Refractive index (n D ) 1,432
Chemical properties
Solubility in water 3,8 g/L
log P 1,40
Family Haloalkine
Dangerousness
Flash point 281 K (8 °C)
Related compounds
chloroalkanes 5-chloro-1-pentyne
6-chloro-1-hexyne
7-chloro-1-heptyne
dichloroalkines 1,4-dicloro-2-butino
cloroalcanos 1-chlorobutane
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 4-chloro-1-butyne , also called 4-chlorobut-1-yne , is an organic compound of molecular formula C 4 H 5 Cl . It is a linear chloroalkyne four carbons with an 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 , 4-chloro-1-butyne is a colorless liquid with a density slightly lower than that of water, ρ ≃ 0.986 g / cm³ . Its boiling point is 96 ° C and its melting point -59 ° C, although both values ​​are estimates. The value of the logarithm of the partition coefficient , log P = 1.40, it indicates that is more soluble in solvents apolar to polar solvents. In water , its solubility is 3.8 g / Lapproximately. [ 3 ] [ 4 ]

Synthesis

4-Chloro-1-butyne is prepared from 3-butynol and a few drops of pyridine in an ice-water bath, to which is added thionyl chloride (SOCl 2 ). The mixture is stirred for 30 minutes, heated to 70 ° C, and refluxed for three and a half hours. [ 5 ]

Applications

4-Chloro-1-butyne can be trimerized using a Ziegler catalyst prepared from titanium (IV) chloride and triisobutylaluminum . As product a mixture of 1,3,5- and 1,2,4-tris (chlorobutyl) benzene is formed. Treatment with sodium acetylide provides the corresponding tributinylbenzenes. [ 6 ]

In the same way, this compound has been used in silyl rodation reactions for the insertion of carbon monoxide in vinyl rhodium complexes. This reaction must be carried out with a low amount of rhodium catalyst (such as Rh 4 (CO) 12 ) and relatively high pressures of carbon monoxide (20-30 atm ). [ 7 ]

The 4-chloro-1-butyne is employed in addition reactions of thiols aromatic , for example phenylthiol , using the Wilkinson catalyst . [ 8 ] It also participates in the synthesis of 4- (4-halo-butyryl) -α, α-dimethyl phenylacetate. key intermediary in the manufacture of the antihistamine fexofenadine . [ 5 ]

See also

The following compounds are isomers of 4-chloro-1-butyne:

References

  1. CAS number
  2. 4-Chloro-1-butyne (PubChem)
  3. a b 4-Chloro-1-butyne (ChemSpider)
  4. a b 4-Chloro-1-butyne (Chemical Book)
  5. a b Synthetic method of 4-(4-halobutyryl)-alpha, alpha-dimethyl phenylacetate (2011) Ding Xiaobo; Lu Xiaoyi; Jiang Shende; Zhang Qiming; Yang Guang; Cai Mingde Patente CN102079708A
  6. Tobe, Y.; Takeda, T. (2010). «45.29.1.1.5.1 Variation 1: By Cyclotrimerization of Alkynes». Science of Synthesis 45: 1336. Consultado el 15 de febrero de 2020.
  7. ^ Anderson, EA; Lim, DSW (2015). "4.4.34.35.3.4 Silylrhodation" . Science of Synthesis Knowledge Updates 1 : 95 . Retrieved February 15, 2020 .
  8. Drabowicz, J.; Kiełbasiński, P.; Mikołajczyk, M. (2007). «33.1.8.1.1.10.3 Variation 3: Metal-Catalyzed Addition of Thiols and Their Borabicyclo Derivatives to Alkynes». Science of Synthesis 43: 143. Consultado el 15 de febrero de 2020.