iodoform iodoform iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the chemical formula chi3. a pale yellow, crystalline, volatile substance, it has 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. iodoform ball and stick model of iodoform names preferred iupac name triiodomethane other names iodoform;carbon triiodide identifiers cas number 75-47-8 y 3d model (jsmol) interactive image beilstein reference 1697010 chebi chebi:37758 y chembl chembl1451116 n chemspider 6134 y echa infocard 100.000.795 ec number 200-874-5 kegg d01910 y mesh iodoform pubchem cid 6374 rtecs number pb7000000 unii kxi2j76489 y comptox dashboard (epa) dtxsid4020743 inchi inchi=1s/chi3/c2-1(3)4/h1h ykey: okjpeaghqzhrqv-uhfffaoysa-n y smiles ic(i)i properties chemical formula chi3 molar mass 393.732 g·mol−1 appearance pale, light yellow, opaque crystals odor saffron-like density 4.008 g cm−3 melting point 119 °c (246 °f; 392 k) boiling point 218 °c (424 °f; 491 k) solubility in water 100 mg l−1 solubility in diethyl ether 136 g l−1 solubility in acetone 120 g l−1 solubility in ethanol 78 g l−1 log p 3.118 henry's lawconstant (kh) 3.4 μmol pa−1 kg−1 magnetic susceptibility (χ) −117.1·10−6 cm3/mol structure crystal structure hexagonal coordination geometry tetragonal molecular shape tetrahedron thermochemistry heat capacity (c) 157.5 j k−1 mol−1 std enthalpy offormation (δfh⦵298) 180.1–182.1 kj mol−1 std enthalpy ofcombustion (δch⦵298) −716.9 – −718.1 kj mol−1 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)1180 mg/kg (dermal, rat)1.6 mmol/kg(s.c., mouse) niosh (us health exposure limits): pel (permissible) none rel (recommended) 0.6 ppm (10 mg/m3) idlh (immediate danger) n.d. related compounds related haloalkanes methyl iodidediiodomethanecarbon tetraiodidechloroformbromoform related compounds guanidinepimagedine except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references iodoform stored in an ampoule structure the molecule adopts tetrahedral molecular geometry with c3v symmetry. synthesis and reactions the synthesis of iodoform was first described by georges-simon serullas in 1822, by reactions of iodine vapour with steam over red-hot coals, and also by reaction of potassium with ethanolic iodine in the presence of water; and at much the same time independently by john thomas cooper. it is synthesized in the haloform reaction by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds: a methyl ketone (ch3cor), acetaldehyde (ch3cho), ethanol (ch3ch2oh), and certain secondary alcohols (ch3chroh, where r is an alkyl or aryl group). the reaction of iodine and base with methyl ketones is so reliable that the iodoform test (the appearance of a yellow precipitate) is used to probe the presence of a methyl ketone. this is also the case when testing for specific secondary alcohols containing at least one methyl group in alpha-position. some reagents (e.g. hydrogen iodide) convert iodoform to diiodomethane. also conversion to carbon dioxide is possible: iodoform reacts with aqueous silver nitrate to produce carbon monoxide. when treated with powdered elemental silver the iodoform is reduced, producing acetylene. upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon. natural occurrence the angel's bonnet mushroom contains iodoform, and shows its characteristic odor. applications the compound finds small-scale use as a disinfectant. around the beginning of the 20th century, it was used in medicine as a healing and antiseptic dressing for wounds and sores and, although this use is now largely superseded by superior antiseptics, it is still used in otolaryngology in the form of bismuth subnitrate iodoform paraffin paste (bipp) as an antiseptic packing for cavities. it is the active ingredient in many ear powders for dogs and cats, along with zinc oxide and propionic acid, which are used to prevent infection and facilitate removal of ear hair.