Chloroform

Chloroform
Names
	Preferred IUPAC name Trichloromethane
	Other names Chloroformium; Freon 20; Methane trichloride; Methyl trichloride; Methenyl trichloride; Methenyl chloride; Refrigerant-20; terchloride/perchloride of formyle (archaic); Trichloretum Formylicum (Latin);
Identifiers
CAS Number	67-66-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	R-20, TCM
ChEBI	CHEBI:35255 ;
ChEMBL	ChEMBL44618 ;
ChemSpider	5977 ;
ECHA InfoCard	100.000.603
EC Number	200-663-8;
KEGG	C13827 ;
PubChem CID	6212;
RTECS number	FS9100000;
UNII	7V31YC746X ;
UN number	1888
CompTox Dashboard (EPA)	DTXSID1020306 ;
	InChI InChI=1S/CHCl3/c2-1(3)4/h1H Key: HEDRZPFGACZZDS-UHFFFAOYSA-N ; InChI=1/CHCl3/c2-1(3)4/h1H Key: HEDRZPFGACZZDS-UHFFFAOYAG;
	SMILES ClC(Cl)Cl;
Properties
Chemical formula	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
Solubility in water	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)
Henry's law; constant (kH)	3.67 L·atm/mol (24 °C)
Acidity (pKa)	15.7 (20 °C)
UV-vis (λmax)	250 nm, 260 nm, 280 nm
Magnetic susceptibility (χ)	−59.30·10−6 cm3/mol
Thermal conductivity	0.13 W/(m·K) (20 °C)
Refractive index (nD)	1.4459 (20 °C)
Viscosity	0.563 cP (20 °C)
Structure
Molecular shape	Tetrahedral
Dipole moment	1.15 D
Thermochemistry
Heat capacity (C)	114.25 J/(mol·K)
Std molar; entropy (S⦵298)	202.9 J/(mol·K)
Std enthalpy of; formation (ΔfH⦵298)	−134.3 kJ/mol
Gibbs free energy (ΔfG⦵)	−71.1 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	473.21 kJ/mol
Pharmacology
ATC code	N01AB02 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Decomposes to extremely toxic phosgene and hydrogen chloride in presence of light – IARC group 2B – Reproductive toxicity – Specific target organ toxicity (STOT)
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H319, H331, H336, H351, H361d, H372
Precautionary statements	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)	2 0 1
Flash point	Nonflammable
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	704 mg/kg (mouse, dermal)
LC50 (median concentration)	47,702 mg/m3 (rat, 4 hr)
LCLo (lowest published)	20,000 ppm (guinea pig, 2 hr); 7,056 ppm (cat, 4 hr); 25,000 ppm (human, 5 min); [clarification needed]
	NIOSH (US health exposure limits):
PEL (Permissible)	50 ppm (240 mg/m3)
REL (Recommended)	Ca ST 2 ppm (9.78 mg/m3) [60-minute]
IDLH (Immediate danger)	500 ppm[clarification needed]
Safety data sheet (SDS)	[1]
Related compounds
Related compounds	Deuterated chloroform CDCl3; Chloromethane CH3Cl; Dichloromethane CH2Cl2; Tetrachloromethane CCl4; Fluoroform CHF3; Bromoform CHBr3; Iodoform CHI3; Chlorodifluoromethane CHF2Cl; Dichlorofluoromethane CHFCl2; Bromodichloromethane CHCl2Br; Dibromochloromethane CHClBr2; Bromodifluoromethane CHF2Br; Dibromofluoromethane CHFBr2;
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). verify (what is ?) Infobox references

Chloroform,^[10] or trichloromethane (often abbreviated as TCM), is an organochloride with the formula C H Cl₃ 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, for this reason, 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).

^ Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177
^ 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
^ "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.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0127". National Institute for Occupational Safety and Health (NIOSH).
^ Toxicity on PubChem Archived 17 August 2018 at the Wayback Machine
^ Lewis, Richard J. (2012). Sax's Dangerous Properties of Industrial Materials (12th ed.). Wiley. ISBN 978-0-470-62325-1.
^ "Chloroform" (PDF). Environmental Protection Agency. September 2016. Retrieved 19 February 2024.
^ "Chloroform". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "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.
^ "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 (inactive 26 April 2024). 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.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
^ 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.
^ "Ether and Chloroform". Archived from the original on 24 March 2018. Retrieved 24 April 2018.
^ "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.

[1] Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177

[2] 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

[3] "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.

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0127". National Institute for Occupational Safety and Health (NIOSH).

[:1-5] Toxicity on PubChem Archived 17 August 2018 at the Wayback Machine

[6] Lewis, Richard J. (2012). Sax's Dangerous Properties of Industrial Materials (12th ed.). Wiley. ISBN 978-0-470-62325-1.

[7] "Chloroform" (PDF). Environmental Protection Agency. September 2016. Retrieved 19 February 2024.

[IDLH-8] "Chloroform". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PubChem-9] "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.

[iupac2013-10] "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 (inactive 26 April 2024). 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.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)

[Ullmann-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.

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