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 into phosgene and hydrogen chloride in presence of heat – likely carcinogenic – reproductive toxicity – hepatotoxic
	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 0
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);
	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
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,^[9] or trichloromethane (often abbreviated as TCM), is an organochloride with the formula CHCl₃ and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and polytetrafluoroethylene (PTFE).^[10] Chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century.^[11]^[12] 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
^ ^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. 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.
^ Rossberg, M.; et al. "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3-527-30673-2.
^ "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 = 20–58. 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

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0127". National Institute for Occupational Safety and Health (NIOSH).

[:1-4] Toxicity on PubChem Archived 17 August 2018 at the Wayback Machine

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

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

[IDLH-7] "Chloroform". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PubChem-8] "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.

[iupac2013-9] "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.

[Ullmann-10] Rossberg, M.; et al. "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3-527-30673-2.

[11] "Ether and Chloroform". Archived from the original on 24 March 2018. Retrieved 24 April 2018.

[12] "Chloroform [MAK Value Documentation, 2000]". The MAK-Collection for Occupational Health and Safety = 20–58. 2012. pp. 20–58. doi:10.1002/3527600418.mb6766e0014. ISBN 978-3-527-60041-0.

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