5-chloro-1-pententine - 5-cloro-1-pentino

5-chloro-1-pententine
5-cloro-1-pentino.tif
5-chloro-1-pentino-3D.gif
IUPAC name
5-chloropent-1-yl
General
Other names 5-chloropentino
4-pentynyl
chloride 1-chloro-4-pentino
Semi-developed formula ClCH2-(CH2)2-C≡C
Molecular formula C 5 H 7 Cl
Identifiers
CAS number 14267-92-6[1]
ChemSpider 76053
PubChem 84308
Physical properties
Appearance Brown liquid
Odor Toilet
Density 960 kg/; 0,96 g/cm³
Molar mass 102.56 g / mol
Melting point −46 °C (227 K)
Boiling point 113 °C (386 K)
Vapor pressure 20,4 ± 0,2 mmHg
Refractive index (n D ) 1,444
Chemical properties
Solubility in water 625 mg / L
log P 1,85
Family Haloalkine
Dangerousness
Flash point 288 K (15 °C)
NFPA 704

NFPA 704.svg

3
2
0
Related compounds
chloroalkanes 4-chloro-1-butyne
6-chloro-1-hexyne
7-chloro-1-heptyne
cloroalcanos 1-chloropentane
chloroalkenes 5-chloro-1-pentene
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 5-chloro-1-pentyne , also called 5-chloropent-1-yne and chloride 4-pentynyl , is an organic compound of formula molecular C 5 H 7 Cl . It is a linear chloroalkyne five 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 , 5-chloro-1-pentine is an odorless brown liquid . It has a density lower than that of water, ρ = 0.960 g / cm³ , while as steam it is 3.54 times more dense than air. Its boiling point is 113 ° C (68 ° C at a pressure of only 145 mmHg) and its melting point is -46 ° C, the latter being an estimated value. [ 3 ]

The value of the logarithm of the partition coefficient , log P = 1.85, it indicates that it is soluble in solvents apolar to polar solvents. In water , its solubility is approximately 625 mg / L. [ 3 ]

Regarding its reactivity , it is incompatible with strong oxidizing agents and strong bases . [ 5 ]

Synthesis

The 5-chloro-1-pentyne is prepared by reacting, in a first step, tropone in dichloromethane with oxalyl chloride ; subsequently 5-pentin-1-ol is added at 75 ºC, reaching a yield of 82%. [ 6 ]

Applications

5-chloro-1-pentyne has been used in the alkenylation of nitrones , giving rise to N- propargyl hydroxylamines , [ 7 ] and in oxidative cross- coupling reactions with N , N , 4-trimethylaniline. [ 8 ] Also in the synthesis of 5-chloro-2-trimethylstanil-1-pentene, by reaction with Me 3 SnCu · Me 2 S, and in that of pyrazoles with α-diazoesters catalyzed by copper . [ 9 ]

From 5-chloro-1-pentyne can be prepared cyclopropylacetylene , reactive in the synthesis of ( S ) -6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin- 2-one, inhibitor reverse transcriptase of the human immunodeficiency virus (HIV). To do this, the 5-chloro-1-pentyne is treated with a strong base - such as n-hexyl-lithium or n-butyll-lithium - and the cyclopropylacetylide is formed, to which a solvent is added . The resulting mixture is distilled under vacuum to reduce the volume and then contacted with a cooling agent, yielding cyclopropylacetylene. [ 10 ]

This chloroalkyne was used to produce nanoparticles of silicon PEGylated soluble in water. [ 11 ]

Precautions

5-chloro-1-pentyne is a compound flammable whose flash point is 15 ° 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 ]

See also

The following compounds are isomers of 5-chloro-1-pentyne:

References

  1. CAS number
  2. 5-Chloro-1-pentyne (PubChem)
  3. a b c 5-Chloro-1-pentyne (ChemSpider)
  4. 5-Chloro-1-pentyne (Chemical Book)
  5. a b 5-Chloro-1-pentyne. MSDS (Thermo Fisher)
  6. Nguyen, T.V.; Bekensir, A. (2014). «Aromatic Cation Activation: Nucleophilic Substitution of Alcohols and Carboxylic Acids». Org. Lett. 16 (6): 1720-1723. Consultado el 13 de febrero de 2020.
  7. Elie, M.; Renaud, J.-L.; Gaillard, S (2016). «1.3.3.1 Alkenylation of Nitrones». Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1: 254. Consultado el 13 de febrero de 2020.
  8. Ipaktschi, J.; Saidi, M. R. (2012). «40.1.1.5.6.2.1.2 Variation 2: Alkynylation of Tertiary Amines Catalyzed by Iron(II) Chloride». Science of Synthesis Knowledge Updates 4: 375. Consultado el 13 de febrero de 2020.
  9. Qi, X.; Ready, J.M. (2007). «Copper‐Promoted Cycloaddition of Diazocarbonyl Compounds and Acetylides». Angewandte Chemie 46 (18): 3242-3244. Consultado el 13 de febrero de 2020.
  10. An improved synthesis of cyclopropylacetylene (1977) Parsons Jr., R.L. Patente WO1998027034A1
  11. Xu, Z., Li, Y., Zhang, B. et al. (2015). «Water-soluble PEGylated silicon nanoparticles and their assembly into swellable nanoparticle aggregates». Journal of Nanoparticle Research 17 (56). Consultado el 13 de febrero de 2020.