In terms of scale, the most important reaction of chloroform is with
hydrogen fluoride to give
monochlorodifluoromethane (HCFC-22), a precursor in the production of polytetrafluoroethylene (
Teflon) and other fluoropolymers:
Solvent The
hydrogen attached to
carbon in chloroform participates in hydrogen bonding, making it a good solvent for many materials. Worldwide, chloroform is also used in pesticide formulations, as a
solvent for
lipids,
rubber,
alkaloids,
waxes,
gutta-percha, and
resins, as a cleaning agent, as a grain
fumigant, in
fire extinguishers, and in the rubber industry. deuterated chloroform| is a common solvent used in
NMR spectroscopy.
Refrigerant Chloroform is used as a precursor to make R-22 (chlorodifluoromethane). This is done by reacting it with
hydrofluoric acid (HF) which fluorinates the molecule and releases hydrochloric acid as a byproduct. Before the
Montreal Protocol was enforced, most of the chloroform produced in the United States was used in the production of
chlorodifluoromethane. However, its production remains high, as it is a key precursor of PTFE. Although chloroform has properties such as a low boiling point, and a low global warming potential of only 31 (compared to the 1760 of R-22), which are appealing properties for a refrigerant, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.
Lewis acid In solvents such as and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. is classified as a
hard acid, and the
ECW model lists its acid parameters as EA = 1.56 and CA = 0.44.
Reagent As a
reagent, chloroform serves as a source of the
dichlorocarbene intermediate . It reacts with aqueous
sodium hydroxide, usually in the presence of a
phase transfer catalyst, to produce
dichlorocarbene, . This reagent effects ortho-formylation of activated
aromatic rings, such as
phenols, producing aryl
aldehydes in a reaction known as the
Reimer–Tiemann reaction. Alternatively, the
carbene can be trapped by an
alkene to form a
cyclopropane derivative. In the
Kharasch addition, chloroform forms the free radical which adds to alkenes.
Anaesthetic Chloroform is a powerful
general anesthetic,
euphoriant,
anxiolytic, and
sedative when inhaled or ingested. The
anaesthetic qualities of chloroform were first described in 1842 in a thesis by
Robert Mortimer Glover, which won the Gold Medal of the
Harveian Society for that year. Glover also undertook practical experiments on dogs to prove his theories, refined his theories, and presented them in his doctoral thesis at the
University of Edinburgh in the summer of 1847, identifying anaesthetizing halogenous compounds as a "new order of poisonous substances". A few days later, during the course of a dental procedure in
Edinburgh,
Francis Brodie Imlach became the first person to use chloroform on a patient in a clinical context. In May 1848,
Robert Halliday Gunning made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory
experiments on rabbits that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments that proved the dangers of chloroform were largely ignored. The use of chloroform during
surgery expanded rapidly in Europe; in the 1850s chloroform was used by the physician
John Snow during the births of
Queen Victoria's last two children
Leopold and
Beatrice. In the United States, chloroform began to replace
ether as an anesthetic at the beginning of the 20th century; it was abandoned in favor of ether on discovery of its toxicity, especially its tendency to cause fatal
cardiac arrhythmias analogous to what is now termed "
sudden sniffer's death". Some people used chloroform as a recreational drug or to attempt suicide. One possible mechanism of action of chloroform is that it increases the movement of
potassium ions through certain types of
potassium channels in
nerve cells. Chloroform could also be mixed with other anesthetic agents such as ether to make C.E. mixture, or ether and
alcohol to make
A.C.E. mixture. In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic. Her autopsy establishing the cause of death was undertaken by
John Fife assisted by
Robert Mortimer Glover. Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. In Germany, comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897. and compiled a report detailing numerous adverse reactions to anesthetics, including chloroform. In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas with chloroform the chances were between 1:3,000 and 1:6,000. The latest reported anaesthetic use of chloroform in the Western world dates to 1987, when the last doctor who used it retired, about 140 years after its first use.
Recreational use In the 1910s in England, a fast-living set called
The Coterie used chloroform recreationally.
Margot Asquith, the wife of the Prime Minister, whose stepson
Raymond Asquith was a member, recorded that
Lady Diana Manners, who called it "jolly old chlorors", had said "I must be unconscious by midnight."
Criminal use Chloroform has been used by criminals to knock out, daze, or murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.
Serial killer H. H. Holmes used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman
William Marsh Rice. The serial killer
John Wayne Gacy chloroformed many of his victims. Chloroform was deemed a factor in the alleged murder of a woman in 1991, when she was asphyxiated while asleep. In 2002, 13-year-old
Kacie Woody was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her. In a 2007 plea bargain, a man confessed to using
stun guns and chloroform to sexually assault minors. The use of chloroform as an
incapacitating agent has become widely recognized, bordering on
cliché, through the adoption by
crime fiction authors of plots involving criminals' use of chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this way. It takes at least five minutes of inhalation of chloroform to render a person unconscious. Most criminal cases involving chloroform involve co-administration of another drug, such as
alcohol or
diazepam, or the victim being complicit in its administration. After a person has lost consciousness owing to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure, typically requiring the skills of an
anesthesiologist. In 1865, as a direct result of the criminal reputation chloroform had gained, the medical journal
The Lancet offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. loss of consciousness, using chloroform. ==Safety==