Organochlorine chemistry
[citation needed] Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.
[6] In addition, a variety of simple chlorinated hydrocarbons including dichloromethane, chloroform, and carbon tetrachloride have been isolated from marine algae.
[8] The natural organochloride epibatidine, an alkaloid isolated from tree frogs, has potent analgesic effects and has stimulated research into new pain medication.
[2] The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds.
[citation needed] Chlorine adds to the multiple bonds on alkenes and alkynes as well, giving di- or tetra-chloro compounds.
In the laboratory, the related reaction involving zinc chloride in concentrated hydrochloric acid: Called the Lucas reagent, this mixture was once used in qualitative organic analysis for classifying alcohols.
Tetraethyllead was produced from ethyl chloride and a sodium–lead alloy:[11][12] Reductive dechlorination is rarely useful in chemical synthesis, but is a key step in the biodegradation of several organochlorine persistent pollutants.
[citation needed] Most low molecular weight and liquid chlorinated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethylene, trichloroethylene, tetrachloroethylene, 1,2-Dichloroethane and hexachlorobutadiene are useful solvents.
[citation needed] Some, like carbon tetrachloride and 1,1,1-Trichloroethane have been phased out due to their toxicity or negative environmental impact (ozone depletion by 1,1,1-Trichloroethane).
Historically significant (as an anaesthetic), but smaller in scale is chloroform, mainly a precursor to chlorodifluoromethane (CHClF2) and tetrafluoroethene which is used in the manufacture of Teflon.
For example, DDT, which was widely used to control insects in the mid-20th century, also accumulates in food chains, as do its metabolites DDE and DDD, and causes reproductive problems (e.g., eggshell thinning) in certain bird species.
For example, peas and broad beans contain the natural chlorinated plant hormone 4-chloroindole-3-acetic acid (4-Cl-IAA);[16][17] and the sweetener sucralose (Splenda) is widely used in diet products.
As of 2004[update], at least 165 organochlorides had been approved worldwide for use as pharmaceutical drugs, including the natural antibiotic vancomycin, the antihistamine loratadine (Claritin), the antidepressant sertraline (Zoloft), the anti-epileptic lamotrigine (Lamictal), and the inhalation anesthetic isoflurane.
