Chloroform is an organic compound with formula CHCl₃. It is a colorless, sweet-smelling, dense liquid that is produced on a large scale as a precursor to PTFE and refrigerants, but the latter application is declining. It is one of the four chloromethanes and a trihalomethane.

Structure

The molecule adopts tetrahedral molecular geometry with C_3vsymmetry.

Natural occurrence

The total global flux of chloroform through the environment is approximately 660 000 tonnes per year, and about 90% of emissions are natural in origin. Many kinds of seaweed produce chloroform, and fungi are believed to produce chloroform in soil.

Chloroform volatilizes readily from soil and surface water and undergoes degradation in air to produce phosgene, dichloromethane, formyl chloride, carbon monoxide, carbon dioxide, and hydrogen chloride. Its halflife in air ranges from 55 to 620 days. Biodegradation in water and soil is slow. Chloroform does not significantly bioaccumulate in aquatic organisms.

History

Chloroform was synthesized independently by two groups in 1831: Liebig carried out the alkaline cleavage of chloral, whereas Soubeirain obtained the compound by the action of chlorine bleach on both ethanol and acetone. In 1835, Dumas prepared the substance by the alkaline cleavage of trichloroacetic acid. Regnault prepared trichloromethane by chlorination of monochloromethane. By the 1850s, chloroform was being produced on a commercial basis by using the Liebig procedure, which retained its importance until the 1960s. Today, trichloromethane — along with dichloromethane — is prepared exclusively and on a massive scale by the chlorination of methane and monochloromethane.

This page provides supplementary chemical data on chloroform.

Material Safety Data Sheet

The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet (MSDS) for this chemical from a reliable source and follow its directions.

Structure and properties

Thermodynamic properties

Vapor pressure of liquid

Table data obtained from CRC Handbook of Chemistry and Physics 44th ed.

Distillation data

Spectral data

References

"Chloroform" is a song written and performed by Phoenix, issued as the first promotional single from the band's fifth studio album Bankrupt!. The official remix of the song features noise pop band Sleigh Bells.

On 30 April 2013, the band performed the song on Late Show with David Letterman during the Live on Letterman webcast that also featured performances of several of their other songs.

Music video

Although the song was not issued as an official single, a music video was created for the song, directed by Sofia Coppola (the wife of lead singer Thomas Mars).

Critical reception

The song has received positive reviews from critics. Jon Dolan of Rolling Stone referred to the song as "restrained pout soul"; while Chris Payne of Billboard called the song a highlight and complimented its "balmy, tropical feel" while comparing it favorably to the work of Delorean and The Tough Alliance. Steven Arroyo of TIME highlighted the song as one of the best songs on the album (along with official lead single "Entertainment" and album cut "Bourgeois").