7-chloro-1-heptin - 7-cloro-1-heptino

7-chloro-1-heptin
7-cloro-1-heptino.tif
7-cloro-1-heptino-3D.gif
IUPAC name
7-clorohept-1-ino
General
Other names 1-chloro-6-heptin
Semi-developed formula ClCH2-(CH2)4-C≡C
Molecular formula C 7 H 11 Cl
Identifiers
CAS number 18804-36-9[1]
ChemSpider 239280
PubChem 272000
Physical properties
Appearance Liquid
Density 940 kg/; 0,94 g/cm³
Molar mass 130.61 g / mol
Melting point −22 °C (251 K)
Boiling point 165 °C (438 K)
Vapor pressure 2,5 ± 0,3 mmHg
Refractive index (n D ) 1,446
Chemical properties
Solubility in water 150 mg / L
log P 2,897
Family Haloalkine
Dangerousness
Flash point 322 K (49 °C)
Related compounds
chloroalkanes 5-chloro-1-pentyne
6-chloro-1-hexyne
8-chloro-1-octino
cloroalcanos 1-cloroheptano
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 7-chloro-1-heptyne , also called 7-clorohept-1-yne or 1-chloro-6-heptyne , is an organic compound of molecular formula C 7 H 11 Cl . It is a linear chloroalkyne seven 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 ]

Physical and chemical properties

At room temperature , 7-chloro-1-heptino is a liquid with a density lower than that of water, ρ ≃ 0.94 g / cm³ . Its boiling point is 165 ° C and its melting point is -22 ° C, both of which are estimated values. The value of the logarithm of its partition coefficient , log P = 2,897, indicates that it is more soluble in nonpolar solvents than in polar solvents. In water , its solubility is approximately 150 mg / L.[3]

Synthesis

7-Chloro-1-heptin can be obtained by treating 1-chloro-5-iodopentane with dry tetrahydrofuran (THF) and HMPA at -30 ° C under nitrogen atmosphere . [ 4 ] It can also be prepared from 1-chloro-5-iodobutane and sodium acetylide in liquid ammonia . [ 5 ]

Applications

7-Chloro-1-heptin is a precursor in the synthesis of 10-hydroxyhexadec-7-ene-1-oic acid , making it react with n-butyllithium to form an organometallic compound , which in turn reacts with 1, 2-epoxyoctane . [ 5 ] It can also be used in the preparation of homologues and derivatives of 9-oxo-13-trans-prostenamide and 9-hydroxy-13-trans-prostenamide, compounds that show antimicrobial and hypotensive activity similar to prostaglandin . [ 6 ]

7-Chloro-1-heptin can be trimerized using a Ziegler catalyst prepared from titanium (IV) chloride and triisobutylaluminum . The product is a mixture of 1,3,5- and 1,2,4-tris (chloroheptyl) benzene. Treatment with sodium acetylide provides the corresponding triheptinylbenzenes. [ 7 ]

References