Chloroform

Chloroform
Chloroform in its liquid state shown in a test tube
Names
Preferred IUPAC name
Trichloromethane
Other names
  • Chloroform[1]
  • Chloroformium
  • Freon 20
  • Methane trichloride
  • Methyl trichloride
  • Methenyl trichloride
  • Methenyl chloride
  • Refrigerant-20
  • terchloride/perchloride of formyle[2][3] (archaic)
  • Trichloretum Formylicum (Latin)
Identifiers
3D model (JSmol)
Abbreviations R-20, TCM
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.603 Edit this at Wikidata
EC Number
  • 200-663-8
KEGG
RTECS number
  • FS9100000
UNII
UN number 1888
  • InChI=1S/CHCl3/c2-1(3)4/h1H checkY
    Key: HEDRZPFGACZZDS-UHFFFAOYSA-N checkY
  • InChI=1/CHCl3/c2-1(3)4/h1H
    Key: HEDRZPFGACZZDS-UHFFFAOYAG
  • ClC(Cl)Cl
Properties
CHCl3
Molar mass 119.37 g·mol−1
Appearance Highly refractive colorless liquid
Odor Sweet, minty, pleasant
Density 1.564 g/cm3 (−20 °C)
1.489 g/cm3 (25 °C)
1.394 g/cm3 (60 °C)
Melting point −63.5 °C (−82.3 °F; 209.7 K)
Boiling point 61.15 °C (142.07 °F; 334.30 K)
decomposes at 450 °C
10.62 g/L (0 °C)
8.09 g/L (20 °C)
7.32 g/L (60 °C)
Solubility Soluble in benzene
Miscible in diethyl ether, oils, ligroin, alcohol, CCl4, CS2
Solubility in acetone ≥ 100 g/L (19 °C)
Solubility in dimethyl sulfoxide ≥ 100 g/L (19 °C)
Vapor pressure 0.62 kPa (−40 °C)
7.89 kPa (0 °C)
25.9 kPa (25 °C)
313 kPa (100 °C)
2.26 MPa (200 °C)
3.67 L·atm/mol (24 °C)
Acidity (pKa) 15.7 (20 °C)
UV-vismax) 250 nm, 260 nm, 280 nm
−59.30·10−6 cm3/mol
Thermal conductivity 0.13 W/(m·K) (20 °C)
1.4459 (20 °C)
Viscosity 0.563 cP (20 °C)
Structure
Tetrahedral
1.15 D
Thermochemistry
114.25 J/(mol·K)
202.9 J/(mol·K)
−134.3 kJ/mol
−71.1 kJ/mol
473.21 kJ/mol
Pharmacology
N01AB02 (WHO)
Hazards[10]
Occupational safety and health (OHS/OSH):
Main hazards
Decomposes to extremely toxic phosgene and hydrogen chloride in presence of light – IARC group 2BReproductive toxicitySpecific target organ toxicity (STOT)[4][5][6]
GHS labelling:
GHS06: Toxic GHS08: Health hazard GHS05: Corrosive
Danger
H302, H315, H319, H331, H336, H351, H361d, H372
P201, P202, P235, P260, P264, P270, P271, P280, P281, P301+P330+P331, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P314, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
0
1
Flash point Nonflammable
Lethal dose or concentration (LD, LC):
704 mg/kg (mouse, dermal)[7]
47,702 mg/m3 (rat, 4 hr)[8]
  • 20,000 ppm (guinea pig, 2 hr)
  • 7,056 ppm (cat, 4 hr)
  • 25,000 ppm (human, 5 min)
[9][clarification needed]
NIOSH (US health exposure limits):
PEL (Permissible)
50 ppm (240 mg/m3)[5]
REL (Recommended)
Ca ST 2 ppm (9.78 mg/m3) [60-minute][5]
IDLH (Immediate danger)
500 ppm[5][clarification needed]
Safety data sheet (SDS) [1]
Related compounds
Related compounds
Supplementary data page
Chloroform (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Chloroform, or trichloromethane (often abbreviated as TCM), is an organic compound with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and PTFE.[11] Chloroform is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Chloroform was used as an anesthetic between the 19th century and the first half of the 20th century.[12][13] It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C).

  1. ^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 661. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names 'bromoform' for HCBr3, 'chloroform' for HCCl3, and 'iodoform' for HCI3 are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.
  2. ^ Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177
  3. ^ Daniel Pereira Gardner, Medicinal Chemistry for the Use of Students and the Profession: Being a Manual of the Science, with Its Applications to Toxicology, Physiology, Therapeutics, Hygiene, Etc (1848), page 271
  4. ^ "Part 3 Health Hazards" (PDF). Globally Harmonized System of Classification and Labelling of Chemicals (GHS). Second revised edition. United Nations. Archived (PDF) from the original on 4 March 2019. Retrieved 30 September 2017.
  5. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0127". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ Toxicity on PubChem Archived 17 August 2018 at the Wayback Machine
  7. ^ Lewis, Richard J. (2012). Sax's Dangerous Properties of Industrial Materials (12th ed.). Wiley. ISBN 978-0-470-62325-1.
  8. ^ "Chloroform" (PDF). Environmental Protection Agency. September 2016. Retrieved 19 February 2024.
  9. ^ "Chloroform". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  10. ^ "PubChem: Safety and Hazards – GHS Classification". National Center for Biotechnology Information, U.S. National Library of Medicine. Archived from the original on 17 August 2018. Retrieved 17 August 2018.
  11. ^ Rossberg, M.; et al. "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3527306732.
  12. ^ "Ether and Chloroform". Archived from the original on 24 March 2018. Retrieved 24 April 2018.
  13. ^ "Chloroform [MAK Value Documentation, 2000]". The MAK-Collection for Occupational Health and Safety. 2012. pp. 20–58. doi:10.1002/3527600418.mb6766e0014. ISBN 978-3-527-60041-0.