For use of the term "iodoform" in cryptography, see Group key.
Iodoform
Ball and stick model of iodoform
Names
Preferred IUPAC name
Triiodomethane
Other names
Iodoform[1]
Carbon hydride triiodide
Carbon triiodide[2]
Identifiers
CAS Number
75-47-8Y
3D model (JSmol)
Interactive image
Beilstein Reference
1697010
ChEBI
CHEBI:37758Y
ChEMBL
ChEMBL1451116N
ChemSpider
6134Y
ECHA InfoCard
100.000.795
EC Number
200-874-5
KEGG
D01910Y
MeSH
iodoform
PubChem CID
6374
RTECS number
PB7000000
UNII
KXI2J76489Y
CompTox Dashboard (EPA)
DTXSID4020743
InChI
InChI=1S/CHI3/c2-1(3)4/h1HY
Key: OKJPEAGHQZHRQV-UHFFFAOYSA-NY
SMILES
IC(I)I
Properties
Chemical formula
CHI3
Molar mass
393.732 g·mol−1
Appearance
Pale, light yellow, opaque crystals
Odor
Saffron-like[3]
Density
4.008 g/cm3[3]
Melting point
119 °C (246 °F; 392 K)[3]
Boiling point
218 °C (424 °F; 491 K)[3]
Solubility in water
100 mg/L[3]
Solubility in diethyl ether
136 g/L
Solubility in acetone
120 g/L
Solubility in ethanol
78 g/L
log P
3.118
Henry's law constant (kH)
3.4 μmol·Pa−1·kg−1
Magnetic susceptibility (χ)
−117.1·10−6 cm3/mol
Structure
Crystal structure
Hexagonal
Molecular shape
Tetrahedral at C
Thermochemistry
Heat capacity (C)
157.5 J/(K·mol)
Std enthalpy of formation (ΔfH⦵298)
180.1 – 182.1 kJ/mol
Std enthalpy of combustion (ΔcH⦵298)
−716.9 – −718.1 kJ/mol
Pharmacology
ATC code
D09AA13 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
2
1
1
Flash point
204 °C (399 °F; 477 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
355 mg/kg (oral, rat)[3]
1180 mg/kg (dermal, rat)[3]
1.6 mmol/kg(s.c., mouse)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
none[4]
REL (Recommended)
0.6 ppm (10 mg/m3)[4]
IDLH (Immediate danger)
N.D.[4]
Related compounds
Related compounds
Methyl iodide
Diiodomethane
Carbon tetraiodide
Fluoroform
Chloroform
Bromoform
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
Iodoform stored in an ampoule
Iodoform (also known as triiodomethane) is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.
^"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.
^"Iodoform".
^ abcdefgRecord in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ abcNIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).
Iodoform (also known as triiodomethane) is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance...
groups (R−C(=O)OH) or to produce chloroform (CHCl3), bromoform (CHBr3), or iodoform (CHI3). Note that fluoroform (CHF3) can't be prepared in this way. In the...
treatments of iodoform, a then experimental form of chemotherapy. Klara Hitler's mastectomy incisions were reopened and massive doses of iodoform-soaked gauze...
parts of North Africa, North America, and Oceania. Saffron's taste and iodoform-like or hay-like fragrance result from the phytochemicals picrocrocin and...
the haloforms — specifically, chloroform (CHCl3), bromoform (CHBr3), and iodoform (CHI3) — are easy to prepare through the haloform reaction, although this...
The retained names 'bromoform' for HCBr3, 'chloroform' for HCCl3, and 'iodoform' for HCI3 are acceptable in general nomenclature. Preferred IUPAC names...
from the reaction mixture. Iodomethane may also be prepared by treating iodoform with potassium hydroxide and dimethyl sulfate under 95% ethanol. Like many...
Alternatively, it can be prepared by the reaction of cyclohexane and iodoform. Iodocyclohexane forms colorless to slightly reddish yellow liquid. It...
discovered by Georges-Simon Serullas in 1824, two years after his discovery of iodoform. Many synthesis routes are known. Reaction of chloroform with sodium iodide...
one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory...
Fluoroform was first obtained by Maurice Meslans in the violent reaction of iodoform with dry silver fluoride in 1894. The reaction was improved by Otto Ruff...
on 21 December after intense suffering involving daily medication with iodoform, a foul-smelling and painful corrosive treatment typically used at the...
impregnated cotton pellets, alvogyl (eugenol, iodoform and butamben), dentalone, bismuth subnitrate and iodoform paste (BIPP) on ribbon gauze and metronidazole...
extraction, packing the dry socket with a eugenol-zinc oxide paste on iodoform gauze is effective for reducing acute pain. Eugenol-zinc oxide paste is...
Due to secretions containing elements like iodine, the animals have an iodoform-like smell. Most acorn worms range from 9 to 45 centimetres (3.5 to 17...
Ocean. It is the largest acorn worm currently known, and has a strong iodoform-like odour. It is bioluminescent. Balanoglossus gigas is recorded as growing...
yellow liquid with a pungent odour by Leopold Gmelin. It is decomposed to iodoform by potash. Iodal was discovered and named in 1837. Iodal is synthesised...
well-known uses of organoiodine compounds is the so-called iodoform test, where iodoform (CHI3) is produced by the exhaustive iodination of a methyl...
with Fehling's solution. Methyl ketones give positive results for the iodoform test. Ketones also give positive results when treated with m-dinitrobenzene...
reaction: CH2Cl2 + 2 NaI → CH2I2 + 2 NaCl It can also be prepared by reducing iodoform with elemental phosphorus or sodium arsenite: CHI3 + Na3AsO3 + NaOH → CH2I2...
bromoform and 56,000 tons of bromomethane annually.[clarification needed] The iodoform reaction, which involves degradation of methyl ketones, proceeds by the...
geometry. Carbon tetraiodide is slightly reactive towards water, giving iodoform and I2. It is soluble in nonpolar organic solvents. It decomposes thermally...
afford the university. As a military doctor, he studied the action of iodoform. Due to his work on Neurotomia opticociliaris (or optociliary neurotomy)...
extraction, packing the dry socket with a eugenol-zinc oxide paste on iodoform gauze is effective for reducing acute pain. The placement of a ZOE "temporary"...
change colour on cutting. It is noted by some authors as smelling like ink, iodoform, sweat, or mouldy straw. The spores are 4–6 x 3–4 μm, and are elliptical...
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