1,6-dichlorohexane
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| General | ||||||||||||||||
| Surname | 1,6-dichlorohexane | |||||||||||||||
| other names |
Hexamethylene chloride |
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| Molecular formula | C 6 H 12 Cl 2 | |||||||||||||||
| Brief description |
colorless to yellowish liquid |
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| properties | ||||||||||||||||
| Molar mass | 155.07 g mol −1 | |||||||||||||||
| Physical state |
liquid |
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| density |
1.07 g cm −3 (18 ° C) |
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| Melting point |
−13 ° C |
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| boiling point |
208 ° C |
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| Vapor pressure |
23 h Pa (92 ° C) |
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| solubility |
heavy in water (0.9 g l −1 at 20 ° C) |
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| Refractive index |
1.4572 |
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| 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-dichlorohexane is a chemical compound from the group of haloalkanes . It has the basic structure of n -hexane , which has a chlorine substituent on each of the terminal carbon atoms .
presentation
The compound can be prepared by the reaction of 1,6-hexanediol with thionyl chloride in the presence of a base such as pyridine . The base initially deprotonates the alcohol , which then attacks the sulfur of the thionyl chloride in a nucleophilic manner . Attack by a chloride ion then cleaves the oxidized sulfur compound to form the product.
properties
It is a colorless compound that is liquid at room temperature and boils at 208 ° C.
use
The chloride ions are good leaving groups , which is why substitutions can easily be made at these positions using nucleophiles .
By reacting with potassium hydroxide and sodium formate , cyclization to Oxepan can be achieved.
Individual evidence
- ↑ a b c d e f g h i Entry on 1,6-dichlorohexane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
- ^ A. Müller, W. Vanc: 6-chloro-hexanol- (1), chlorine and oxy-ethers from hexanediol- (1,6). In: monthly Chem. Vol. 77, 1947, pp. 259-263.
- ↑ F. Asinger, B. Fell, H. Scherb: On the knowledge of the products of the joint action of sulfur dioxide and chlorine on aliphatic hydrocarbons in ultraviolet light, XI. About the composition of the sulfochlorination products of n-hexane sulfochloride- (1) , in: Chem. Ber. Vol. 96, 1963, pp. 2831-2840. doi : 10.1002 / cber.19630961103
- ↑ HA Zahalka, Y. Sasson: One-Pot Conversion of Primary Alkyl Chlorides and Dichlorides into Alcohols, Diols, and Ethers via Formic Ester Intermediates under Phase-Transfer Conditions . In: Synthesis . Vol. 9, 1986, pp. 763-765. doi : 10.1055 / s-1986-31769