1,6-diiodohexane

Structural formula
General
Surname	1,6-diiodohexane
other names	Hexamethylene iodide; 1,6-diiodohexane; Hexamethylene iodide;
Molecular formula	C 6 H 12 I 2
Brief description	colorless liquid
External identifiers / databases
EC number	211-073-5
ECHA InfoCard	100.010.067
PubChem	12373
Wikidata	Q161560
properties
Molar mass	337.97 g mol −1
Physical state	liquid
density	2.05 g cm −3
Melting point	9-10 ° C
boiling point	141–142 ° C (13 h Pa )
solubility	almost insoluble in water
Refractive index	1.5852
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 302 + 352-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,6-Diiodohexane is a chemical compound . Their structure is derived from the basic structure of hexane and has an iodine substituent at each end of the chain .

Extraction and presentation

The compound can be obtained from the reaction between 1,6-hexanediol , red phosphorus and elemental iodine. Another possibility is the Finkelstein reaction of 1,6-dibromohexane with sodium iodide .

{\ displaystyle \ mathrm {Br {-} (CH_ {2}) _ {6} {-} Br \ + \ 2 \ NaI \ \ longrightarrow \}}

{\ displaystyle \ mathrm {I {-} (CH_ {2}) _ {6} {-} I \ + \ 2 \ NaBr}}

properties

1,6-Diiodohexane is a yellowish liquid that solidifies at 9–10 ° C and boils at 141–142 ° C at a pressure of 13 hPa. The flash point is 113 ° C.

use

The iodine substituents at the ends of the alkyl chain are excellent leaving groups , which is why 1,6-diiodohexane can be used to synthesize 1,6-hexane derivatives by reacting with nucleophiles . 1,6-Diiodohexane and 1,6- Dibromohexane can be used for the synthesis of Thiepan . To do this, it is reacted with potassium sulfide .

{\ displaystyle \ mathrm {I {-} (CH_ {2}) _ {6} {-} I \ + \ K_ {2} S \ \ longrightarrow \ C_ {6} H_ {12} S \ + \ 2 \ KI}}

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 1,6-diiodohexane, 97%, contains copper as stabilizer from Sigma-Aldrich , accessed on December 25, 2019 ( PDF ).

↑ Data sheet 1,6-Diiodohexane, 98%, stab. with copper at AlfaAesar, accessed December 25, 2019 ( PDF )(JavaScript required) .

↑ A. Müller, E. Rölz: On the action of 1.6-diiodine- n- hexane on amines , in: Chem. Ber. , 1928 , 61 , pp. 570-574; doi : 10.1002 / cber.19280610321 .

↑ F. Asinger, B. Scheuffler: On the influence of sodium salts of hexadecanedicarboxylic acids on the surface-active and washing properties of sodium salts of hexadecane monocarboxylic acids , in: J. Prakt. Chem. , 1960 , 10 , pp. 265-289; doi : 10.1002 / prac.19600100504 .

↑ A. Singh, A. Mehrotra, SL Regen: High Yield Medium Ring Synthesis of Thiacycloalkanes , in: Synth. Commun. , 1981 , 11 , pp. 409-412; doi : 10.1080 / 00397918108064308 .

↑ J. v. Braun: About cyclic sulfides , in: Chem. Ber. , 1910 , 43 , pp. 3220-3226; doi : 10.1002 / cber.19100430387 .

[aldrich-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 1,6-diiodohexane, 97%, contains copper as stabilizer from Sigma-Aldrich , accessed on December 25, 2019 ( PDF ).

[Alfa-2] Data sheet 1,6-Diiodohexane, 98%, stab. with copper at AlfaAesar, accessed December 25, 2019 ( PDF )(JavaScript required) .

[3] A. Müller, E. Rölz: On the action of 1.6-diiodine- n- hexane on amines , in: Chem. Ber. , 1928 , 61 , pp. 570-574; doi : 10.1002 / cber.19280610321 .