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Chloroform

Chloroform
Chloroform displayed.svg
Chloroform 3D.svg
Chloroform in its liquid state shown in a test tube
Names
Preferred IUPAC name
Trichloromethane
Other names
Chloroform
Methane trichloride
Methyl trichloride
Methenyl trichloride
TCM
Freon 20
Refrigerant-20
R-20
UN 1888
Identifiers
67-66-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:35255 YesY
ChEMBL ChEMBL44618 YesY
ChemSpider 5977 YesY
ECHA InfoCard 100.000.603
EC Number 200-663-8
KEGG C13827 YesY
PubChem 6212
RTECS number FS9100000
UNII 7V31YC746X YesY
Properties
CHCl3
Molar mass 119.37 g·mol−1
Appearance Colorless liquid
Odor Heavy, ethereal odor
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
1.062 g/100 mL (0 °C)
0.809 g/100 mL (20 °C)
0.732 g/100 mL (60 °C)
Solubility Soluble in benzene
Miscible in diethyl ether, oils, ligroin, alcohol, CCl4, CS2
Solubility in acetone ≥ 10 g/100 mL (19 °C)
Solubility in dimethyl sulfoxide ≥ 10 g/100 mL (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
Main hazards carcinogen
Safety data sheet See: data page
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Warning
H302, H315, H319, H332, H336, H351, H361, H373
P261, P281, P305+351+338
Harmful Xn Irritant Xi
Carc. Cat. 2B
R-phrases R22, R38, R40, R48/20/22
S-phrases (S2), S36/37
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1250 mg/kg (rats, oral)
9617 ppm (rat, 4 hr)
20,000 ppm (guinea pig, 2 hr)
7056 ppm (cat, 4 hr)
25,000 ppm (human, 5 min)
US health exposure limits (NIOSH):
PEL (Permissible)
50 ppm (240 mg/m3)
REL (Recommended)
Ca ST 2 ppm (9.78 mg/m3) [60-minute]
IDLH (Immediate danger)
500 ppm
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Chloroform, or trichloromethane, 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.

The molecule adopts tetrahedral molecular geometry with C3vsymmetry.

The total global flux of chloroform through the environment is approximately 660000 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 half-life in air ranges from 55 to 620 days. Biodegradation in water and soil is slow. Chloroform does not significantly bioaccumulate in aquatic organisms.

Chloroform was synthesized independently by several investigators circa 1831:

In industry, chloroform is produced by heating a mixture of chlorine and either chloromethane or methane. At 400–500 °C, a free radical halogenation occurs, converting these precursors to progressively more chlorinated compounds:


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Wikipedia

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