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			{{for|use of the term "iodoform" in cryptography|Group key}}
			{{Use dmy dates|date=April 2017}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 401606384
			| Watchedfields = changed
	| ImageFileL1 = Iodoform.svg
			| verifiedrevid = 444991229
	| ImageSizeL1 = 80px
	| ImageFileR1 = Iodoform-GED-3D-vdW.png		| ImageFile = Iodoform.svg
			| ImageClass = skin-invert
	| ImageSizeR1 = 120px
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile2 = Iodoform2.jpg
			| ImageSize = 100
	| IUPACName = Triiodomethane
			| ImageName = Stereo, skeletal formula of iodoform with the explicit hydrogen added
	| OtherNames = Iodoform, Methyl triiodide, Carbon triiodide, TIM
			| ImageFileL1 = Iodoform-GED-3D-balls.png
	| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
			| ImageNameL1 = Ball and stick model of iodoform
	| ChemSpiderID = 6134
			| ImageFileR1 = Iodoform-GED-3D-vdW.png
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| StdInChI = 1S/CHI3/c2-1(3)4/h1H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| ImageFile2_Ref = {{chemboximage|correct|??}}
			| ImageFile2 = Iodoform in a test tube.jpg
	| StdInChIKey = OKJPEAGHQZHRQV-UHFFFAOYSA-N
			| ImageSize2 =
			| ImageName2 = Freshly made iodoform from an iodine tincture.
			| PIN = Triiodomethane
			| OtherNames = {{ubl|Iodoform<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 661 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The retained names ‘bromoform’ for HCBr<sub>3</sub>, ‘chloroform’ for HCCl<sub>3</sub>, and ‘iodoform’ for HCI<sub>3</sub> are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.| chapter = Front Matter }}</ref>|Carbon hydride triiodide|Carbon triiodide<ref name=pubchem>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Iodoform | title=Iodoform }}</ref>}}
			| Section1 = {{Chembox Identifiers
	| CASNo = 75-47-8		| CASNo = 75-47-8
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| EINECS = 200-874-5		| PubChem = 6374
	| PubChem = 6374		| ChemSpiderID = 6134
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| SMILES = IC(I)I
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = KXI2J76489		| UNII = KXI2J76489
			| UNII_Ref = {{fdacite|correct|FDA}}
	| InChI = 1/CHI3/c2-1(3)4/h1H
	| RTECS = PB7000000		| EINECS = 200-874-5
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 37758
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D01910		| KEGG = D01910
			| KEGG_Ref = {{keggcite|correct|kegg}}
	}}
			| MeSHName = iodoform
	| Section2 = {{Chembox Properties
			| ChEBI = 37758
	| Formula = CHI<sub>3</sub>
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| MolarMass = 393.73 g/mol
			| ChEMBL = 1451116
	| Appearance = Yellow crystals
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| Density = 4.008 g/cm<sup>3</sup>
			| RTECS = PB7000000
	| MeltingPt = 123 °C
			| Beilstein = 1697010
	| BoilingPt = 217 °C (expl.)
			| SMILES = IC(I)I
	| Solubility = 0.1 g/L at 20 °C (slightly soluble in ] and ]; moderately soluble in ] and ], highly soluble in ], ] (78 g/L at 25 °C), ] (120 g/L at 25 °C) and ] (136 g/L at 25 °C))
			| StdInChI = 1S/CHI3/c2-1(3)4/h1H
	| LogP = 3.83
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| HenryConstant = 0.34 mol.kg<sup>-1</sup>.bar<sup>-1</sup>
			| StdInChIKey = OKJPEAGHQZHRQV-UHFFFAOYSA-N
	}}
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| Section3 = {{Chembox Structure
			}}
	| CrystalStruct = Hexagonal
			| Section2 = {{Chembox Properties
	| Coordination =
			| C=1|H=1|I=3
	| MolShape = Tetrahedral
			| Appearance = Pale, light yellow, opaque crystals
	}}
			| Odor = Saffron-like<ref name=GESTIS>{{GESTIS|ZVG= 491168}}</ref>
	| Section4 = {{Chembox Hazards
			| Density = 4.008 g/cm<sup>3</sup><ref name=GESTIS/>
	| EUClass = Harmful ('''Xn'''), Dangerous for the environment ('''N''')
	| MainHazards =		| MeltingPtC = 119
			| MeltingPt_ref =<ref name=GESTIS/>
	| RPhrases = {{R20/21/22}}, {{R36/37/38}}
			| BoilingPtC = 218
	| SPhrases = {{S22}}, {{S26}}, {{S36/37/39}}
			| BoilingPt_ref =<ref name=GESTIS/>
	| NFPA-H = 2
			| Solubility = 100 mg/L<ref name=GESTIS/>
	| NFPA-F = 0
			| Solvent1 = diethyl ether
	| NFPA-R = 1
			| Solubility1 = 136 g/L
	| NFPA-O =
	| FlashPt = 204 °C		| Solvent2 = acetone
			| Solubility2 = 120 g/L
	| Autoignition =
			| Solvent3 = ethanol
	}}
			| Solubility3 = 78 g/L
			| LogP = 3.118
			| HenryConstant = 3.4 μmol·Pa<sup>−1</sup>·kg<sup>−1</sup>
			| MagSus = −117.1·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			| Section3 = {{Chembox Structure
			| CrystalStruct = Hexagonal
			| MolShape = ] at ]
			}}
			| Section5 = {{Chembox Thermochemistry
			| DeltaHf = 180.1 – 182.1 kJ/mol
			| DeltaHc = −716.9 – −718.1 kJ/mol
			| HeatCapacity = 157.5 J/(K·mol)
			}}
			| Section6 = {{Chembox Pharmacology
			| ATCCode_prefix = D09
			| ATCCode_suffix = AA13
			}}
			| Section7 = {{Chembox Hazards
			| GHSPictograms = {{gHS exclamation mark}}
			| GHSSignalWord = '''WARNING'''
			| HPhrases = {{h-phrases|315|319|335}}
			| PPhrases = {{p-phrases|261|280|305+351+338}}
			| NFPA-H = 2
			| NFPA-F = 1
			| NFPA-R = 1
			| FlashPtC = 204
			| LD50 = {{ubl|355 mg/kg (oral, rat)<ref name=GESTIS/>|1180 mg/kg (dermal, rat)<ref name=GESTIS/>|1.6 mmol/kg(], mouse)<ref name=Merck>'']'', 12 Edition, '''5054'''</ref>}}
			| IDLH = N.D.<ref name=PGCH>{{PGCH|0343}}</ref>
			| REL = 0.6 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/>
			| PEL = none<ref name=PGCH/>
			}}
			| Section8 = {{Chembox Related
			| OtherFunction_label = haloalkanes
			| OtherCompounds = {{ubl||]|]|]|]|]|]}}
			}}
	}}		}}
			]]]
			'''Iodoform''' (also known as '''triiodomethane''') is the ] with the ] {{chem2|CHI3|auto=1}}. 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 ], sweetish taste. It is occasionally used as a ].
			==Naming==
	'''Iodoform''' is the ] with the ] ]]]<sub>3</sub>. A pale yellow, crystalline, volatile substance, it has a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and, analogous to ], sweetish taste. It is occasionally used as a ]. It is sometimes also referred to as carbon triiodide (which is not strictly correct, as this compound also contains ]) or methyl triiodide (which is somewhat ambiguous as that name could also refer to the methylated ] ion, CH<sub>3</sub>I<sub>3</sub>).
			The name iodoform originates with the "formyle radical," an archaic term for the HC moiety, and is retained for historical consistency. A full, modern name is triiodomethane. The "hydride" in the latter is sometimes omitted,<ref name="pubchem" /> but the IUPAC recommends against doing so, as "carbon triiodide" could also mean {{chem2|C2I6}} (], a highly unstable compound).
			== Structure ==
			The molecule adopts a ] with C<sub>3v</sub> ].
	==Synthesis and reactions==		==Synthesis and reactions==
	Iodoform was first prepared by Georges Serrulas in 1822 and its molecular formula was identified by ] in 1834. It is synthesized in the ] by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds: (i) a methyl ]: CH<sub>3</sub>COR, ] (CH<sub>3</sub>CHO), ] (CH<sub>3</sub>CH<sub>2</sub>OH), and certain secondary ]s (CH<sub>3</sub>CHROH, where R is an alkyl or aryl group).		The synthesis of iodoform was first described by ] 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;<ref>{{citation| first = Georges-Simon|last = Surellas| url = http://gallica.bnf.fr/ark:/12148/bpt6k6137757n/f2.image |title = Notes sur l'Hydriodate de potasse et l'Acide hydriodique. -- Hydriodure de carbone; moyen d'obtenir, à l'instant, ce composé triple|trans-title= Notes on the hydroiodide of potassium and on hydroiodic acid -- hydroiodide of carbon; means of obtaining instantly this compound of three elements| language = French| publisher = Metz, France: Antoine| year= 1822| pages= 17–20, 28–29}}</ref> and at much the same time independently by ].<ref name=ODNB>{{cite ODNB|last=James|first=Frank A. J. L.|title=Cooper, John Thomas |url=http://www.oxforddnb.com/view/article/39361 |access-date=26 January 2012 |doi=10.1093/ref:odnb/39361|year=2004}}</ref> It is synthesized in the ] by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds: a methyl ] ({{chem2|CH3COR}}), ] ({{chem2|CH3CHO}}), ] ({{chem2|CH3CH2OH}}), and certain secondary ]s ({{chem2|CH3CHROH}}, where R is an alkyl or aryl group).
	:]		:]
	The reaction of iodine and base with ]s is so reliable, that the "]" (the appearance of a yellow precipitate) is used to probe the presence of a methyl ketone. This is also the case when testing for ]s (methyl alcohols).		The reaction of iodine and base with ] ]s is so reliable that the ] (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 ]s containing at least one ] group in ].
	Some reagents (e.g. ]) convert iodoform to ]. Also conversion to ] is possible: Iodoform reacts with aqueous ] to produce ], which is oxidized by mixture of ] and ]. When treated with powdered elemental silver the iodoform is reduced, producing ]. Upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon.		Some reagents (e.g. ]) convert iodoform to ]. Also conversion to ] is possible:<ref>{{cite journal |doi= 10.1021/ja01129a067 |title= A Method for the Specific Conversion of Iodoform to Carbon Dioxide |journal= J. Am. Chem. Soc. |year= 1952 |volume= 74 |issue= 9 |pages= 2404 |first1= W. W. |last1= Shreeve |first2= F. |last2= Leaver |first3= I. |last3= Siegel }}</ref> Iodoform reacts with aqueous ] to produce ]. When treated with powdered elemental silver the iodoform is reduced, producing ]. Upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon.
	===Natural occurrence===		===Natural occurrence===
			The ] mushroom contains iodoform, and shows its characteristic odor.
	] contain iodoform and show its characteristic odor.
	==Applications==		==Applications==
	The compound finds small scale use as a disinfectant.<ref>Phyllis A. Lyday "Iodine and Iodine Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref> Around the beginning of the 20th century it was used in medicine as a healing and antiseptic dressing for wounds and sores, although this use is now superseded by superior ]s. ]'s mother, ], died of iodoform poisoning brought on by her treatment for ]. It is the active ingredient in many ear powders for ]s and ]s, to prevent infection and facilitate removal of ear hair, along with ] and propanoic acid.		The compound finds small-scale use as a disinfectant.<ref name=Merck/><ref>{{citation| first = Phyllis A.| last = Lyday |publisher = Wiley-VCH, Weinheim| year = 2005 | doi = 10.1002/14356007.a14_381.pub2 | title = Ullmann's Encyclopedia of Industrial Chemistry | pages = 1–13 | isbn = 9783527306732 | chapter = Iodine and Iodine Compounds }}</ref> 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 ]s, it is still used in ] in the form of ] iodoform ] paste (BIPP) as an antiseptic packing for cavities.<ref>{{cite journal |last1= Randhawa |first1= G. K. |last2= Graham |first2= R. |last3= Matharu |first3= K. S. |title= Bismuth Iodoform Paraffin Paste: History and uses |journal= British Journal of Oral and Maxillofacial Surgery |year= 2019 |volume= 57 |issue= 10 |pages= E53-E54 |doi= 10.1016/j.bjoms.2019.10.153 }}</ref> It is the active ingredient in many ear powders for ]s and ]s, along with ] and ], which are used to prevent infection and facilitate removal of ear hair.{{Citation needed|date=October 2014}}
			==See also==
			* ]
			* ]
			* ]
	==References==		==References==
			{{Reflist}}
	<references/>
	*''Merck Index'', 12 Edition, '''5054'''.
	== See also ==		==External links==
			* {{PGCH|0343}}
	* ]
			*
			* {{Cite EB1911 |wstitle=Iodoform |volume=14 |page=726 |short=1}}
			{{medicated dressings}}
	== External links ==
	*{{PGCH|0343}}		{{halomethanes}}
			{{Authority control}}
	*
	*
	*
	*
	*
			]
	{{Medicated dressings}}
	{{Halomethanes}}
	]
	]		]
	]		]
			]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
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