1,6-dibromohexane

Structural formula
General
Surname	1,6-dibromohexane
other names	Hexamethylene bromide
Molecular formula	C 6 H 12 Br 2
Brief description	colorless liquid
External identifiers / databases
EC number	211-067-2
ECHA InfoCard	100.010.062
PubChem	12368
Wikidata	Q161558
properties
Molar mass	243.98 g mol −1
Physical state	liquid
density	1.61 g cm −3 (20 ° C)
Melting point	−2 ° C
boiling point	243 ° C
solubility	practically insoluble in water
Refractive index	1.5307
safety instructions
H and P phrases	H: 302-317-411
	P: 261-280-301 + 312-302 + 352-333 + 313-501
	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-Dibromohexane is a chemical compound , a derivative of hexane , which has a bromine atom on each of the two terminal chain links . 1,6-Dibromohexane is a colorless liquid with a melting point of −2 ° C and a boiling point of 243 ° C.

presentation

1,6-Dibromohexane can be produced in a substitution reaction from 1,6-hexanediol with hydrobromic acid.

{\ displaystyle \ mathrm {HO {-} (CH_ {2}) _ {6} {-} OH \ + \ 2 \ HBr \ \ longrightarrow}}

{\ displaystyle \ mathrm {Br {-} (CH_ {2}) _ {6} {-} Br \ + \ 2 \ H_ {2} O}}

use

The bromine atoms of the compound represent leaving groups . By substitution reactions at these positions, further hexane derivatives can be obtained. The formation of hexene derivatives by elimination reactions is also possible.

1,6-Dibromohexane can be used analogously to 1,6-Diiodohexane for the synthesis of Thiepan . To do this, it is reacted with sodium sulfide .

{\ displaystyle \ mathrm {Br {-} (CH_ {2}) _ {6} {-} Br \ + \ Na_ {2} S \ longrightarrow \ C_ {6} H_ {12} S \ + \ 2 \ NaBr }}

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1,6-dibromohexane in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
^ WE Vaughan, FF Rust, TW Evans: The Photo-Addition of hydrogen bromide to olefinic bonds , in: J. Org. Chem. , 1942 , 7 , pp. 477-490; doi : 10.1021 / jo01200a005 .
↑ A. Müller, A. Sauerwald: New synthesis of 1,6-dibromo-n-hexane and its effect on p-toluenesulfamide , in : months. Chem. , 1927 , 48 , pp. 521-527; doi : 10.1007 / BF01518069 .
↑ J. v. Braun: About cyclic sulfides , in: Chem. Ber. , 1910 , 43 , pp. 3220-3226; doi : 10.1002 / cber.19100430387 .
↑ 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 .

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1,6-dibromohexane in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[2] WE Vaughan, FF Rust, TW Evans: The Photo-Addition of hydrogen bromide to olefinic bonds , in: J. Org. Chem. , 1942 , 7 , pp. 477-490; doi : 10.1021 / jo01200a005 .

[3] A. Müller, A. Sauerwald: New synthesis of 1,6-dibromo-n-hexane and its effect on p-toluenesulfamide , in : months. Chem. , 1927 , 48 , pp. 521-527; doi : 10.1007 / BF01518069 .

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

[5] 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 .