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sweet smelling yellow solid haloform CHI3 (同)tri-iodomethane
a yellowish crystalline solid with a penetrating odor; sometimes used as an antiseptic dressing (同)triiodomethane

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2019/05/14 09:10:18」(JST)

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Iodoform (also known as triiodomethane and carbon triiodide) is the organoiodine compound with the 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 the smell of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

Structure

The molecule adopts tetrahedral molecular geometry with C_3v 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;^[5] and at much the same time independently by John Thomas Cooper.^[6] 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.^[4]^[7] 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 antiseptics. It is the active ingredient in many ear powders for dogs and cats, along with zinc oxide and propanoic acid, which are used to prevent infection and facilitate removal of ear hair.^{[citation needed]}

References

^ "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.
^ ^a ^b ^c ^d ^e ^f ^g Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b Merck Index, 12 Edition, 5054
^ Surellas, Georges-Simon (1822), Notes sur l'Hydriodate de potasse et l'Acide hydriodique. -- Hydriodure de carbone; moyen d'obtenir, à l'instant, ce composé triple [Notes on the hydroiodide of potassium and on hydroiodic acid -- hydroiodide of carbon; means of obtaining instantly this compound of three elements] (in French), Metz, France: Antoine, pp. 17–20, 28–29
^ James, Frank A. J. L. "Cooper, John Thomas (1790–1854), chemist". Oxford Dictionary of National Biography. Oxford University Press. Retrieved 26 January 2012.
^ Lyday, Phyllis A. (2005), "Iodine and Iodine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, pp. 1–13, doi:10.1002/14356007.a14_381.pub2, ISBN 9783527306732

External links

NIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).
MSDS at JT Baker
A Method for the Specific Conversion of Iodoform to Carbon Dioxide
"Iodoform" . Encyclopædia Britannica. 14 (11th ed.). 1911. p. 726.

UpToDate Contents

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2. 鼻出血を有する成人へのアプローチ approach to the adult with epistaxis

English Journal

Rapid oxidation of iodide and hypoiodous acid with ferrate and no formation of iodoform and monoiodoacetic acid in the ferrate/I^-/HA system.

Wang X1, Liu Y1, Huang Z1, Wang L2, Wang Y1, Li Y1, Li J1, Qi J1, Ma J3.
Water research.Water Res.2018 Nov 1;144:592-602. doi: 10.1016/j.watres.2018.07.061. Epub 2018 Jul 27.
PMID 30092505

Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings.

Keglevich A1, Mayer S2, Pápai R3, Szigetvári Á4, Sánta Z5, Dékány M6, Szántay C Jr7, Keglevich P8, Hazai L9.
Molecules (Basel, Switzerland).Molecules.2018 Oct 9;23(10). pii: E2574. doi: 10.3390/molecules23102574.
PMID 30304796

A new section and species of AgaricussubgenusPseudochitonia from Thailand.

He MQ1,2,3, Chuankid B3, Hyde KD3, Ratchadawan Cheewangkoon1, Zhao RL2,4.
MycoKeys.MycoKeys.2018 Sep 20;(40):53-67. doi: 10.3897/mycokeys.40.26918. eCollection 2018.
PMID 30271264

A Rare Catch in a Nonhealing Wound.

Agrawal T1, Fuentes Rojas S1, Adigun R1, Badam M1.
Wounds : a compendium of clinical research and practice.Wounds.2018 Sep;30(9):E87-E88.
PMID 30256755

Japanese Journal

Effects of zinc oxide-eugenol and calcium hydroxide/ iodoform on delaying root resorption in primary molars without successors

LIN Bichen,ZHAO Yuming,YANG Jie,WANG Wenjun,GE Li-hong
Dental Materials Journal 33(4), 471-475, 2014
… The purpose of this study was to compare the effects of zinc oxide-eugenol (ZOE) and calcium hydroxide/iodoform paste (Vitapex), as root canal filling materials in pulpectomy, on delaying the root resorption of primary molars without permanent successors. …
NAID 130004519345

Biocompatibility of Portland cement combined with different radiopacifying agents

Lourenço Neto Natalino,C. T. Marques Nádia,Paula Fernandes Ana,Rodini Camila O.,A. H. Duarte Marco,C. Lima Marta,A. A. M. Machado Maria,C. C. Abdo Ruy,M. Oliveira Thais
Journal of Oral Science 56(1), 29-34, 2014
… The aim of this study was to evaluate the response of rat subcutaneous tissue to Portland cement combined with two different radiopacifying agents, iodoform (CHI3) and zirconium oxide (ZrO2). …
NAID 130003393075

Iodoform Gauze Removes Necrotic Tissue from Pressure Ulcer Wounds by Fibrinolytic Activity

Mizokami Fumihiro,Murasawa Yusuke,Furuta Katsunori [他],Isogai Zenzo
Biological and Pharmaceutical Bulletin 35(7), 1048-1053, 2012
… Iodoform gauze is used in clinical practice for treatment of infected wounds. … However, effectiveness and action mechanism of iodoform gauze for removal of necrotic tissue are unknown. … We therefore employed case control and biochemical studies in order to clarify the pharmacological activity of iodoform gauze. … A clinical study demonstrated that treatment with iodoform gauze removed necrotic tissue more effectively than treatment with conventional ointments. …
NAID 130001872097

Intoxication caused by iodoform gauze packing in necrotizing fasciitis

NAKAMURA Kensuke,INOKUCHI Ryota,FUJITA Hidenobu,HIRUMA Takahiro,MATSUBARA Takehiro,TANAKA Yukio,YAHAGI Naoki
日本集中治療医学会雑誌 = Journal of the Japanese Society of Intensive Care Medicine 18(4), 629-631, 2011-10-01
NAID 10029836109

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リンク元	「ヨードホルム」
拡張検索	「iodoform paste」

「ヨードホルム」

Iodoform
Names
	Preferred IUPAC name Triiodomethane
	Other names Iodoform;; Carbon triiodide
Identifiers
CAS Number	75-47-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1697010
ChEBI	CHEBI:37758 ;
ChEMBL	ChEMBL1451116 ;
ChemSpider	6134 ;
ECHA InfoCard	100.000.795
EC Number	200-874-5
KEGG	D01910 ;
MeSH	iodoform
PubChem CID	6374;
RTECS number	PB7000000
UNII	KXI2J76489 ;
CompTox Dashboard (EPA)	DTXSID4020743 ;
	InChI InChI=1S/CHI3/c2-1(3)4/h1H Key: OKJPEAGHQZHRQV-UHFFFAOYSA-N ;
	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 law; constant (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 of; formation (ΔfH⦵298)	180.1–182.1 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−716.9 – −718.1 kJ mol−1
Pharmacology
ATC code	D09AA13 (WHO)
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P280, P305+351+338
NFPA 704	0 2 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);
	US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	0.6 ppm (10 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related haloalkanes	Methyl iodide; Diiodomethane; Carbon tetraiodide; Chloroform; Bromoform;
Related compounds	Guanidine; Pimagedine;
	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

　　[★]

英: iodoform
ラ: iodoformidum
商: カルビタール、ハクゾウヨードホルム
関: トリヨードメタン triiodomethane; 外皮用殺菌消毒剤

「iodoform paste」

　　[★] ヨードホルムパスタ

[iupac2013-1] "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.

[GESTIS-2] ^ ^a ^b ^c ^d ^e ^f ^g Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).

[Merck-4] Merck Index, 12 Edition, 5054

[5] Surellas, Georges-Simon (1822), Notes sur l'Hydriodate de potasse et l'Acide hydriodique. -- Hydriodure de carbone; moyen d'obtenir, à l'instant, ce composé triple [Notes on the hydroiodide of potassium and on hydroiodic acid -- hydroiodide of carbon; means of obtaining instantly this compound of three elements] (in French), Metz, France: Antoine, pp. 17–20, 28–29

[ODNB-6] James, Frank A. J. L. "Cooper, John Thomas (1790–1854), chemist". Oxford Dictionary of National Biography. Oxford University Press. Retrieved 26 January 2012.

[7] Lyday, Phyllis A. (2005), "Iodine and Iodine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, pp. 1–13, doi:10.1002/14356007.a14_381.pub2, ISBN 9783527306732

v t e Medicated dressings (D09)
Ointment dressings with anti-infectives	Aluminium chlorohydrate Benzalkonium Benzododecinium Cetylpyridinium Chlorhexidine Clioquinol Framycetin Fusidic acid Iodoform Nitrofural Phenylmercuric nitrate Povidone-iodine Triclosan
Other	Soft paraffin dressings Zinc bandages

v t e Halomethanes
Monosubstituted	CH₃F CH₃Cl CH₃Br CH₃I
Disubstituted	CH₂F₂ CH₂ClF CH₂BrF CH₂FI CH₂Cl₂ CH₂BrCl CH₂ClI CH₂Br₂ CH₂BrI CH₂I₂
Trisubstituted	CHF₃ CHClF₂ CHBrF₂ CHF₂I CHCl₂F CHBrClF CHClFI CHBr₂F CHBrFI CHFI₂ CHCl₃ CHBrCl₂ CHCl₂I CHBr₂Cl CHBrClI CHClI₂ CHBr₃ CHBr₂I CHBrI₂ CHI₃
Tetrasubstituted	CF₄ CClF₃ CBrF₃ CF₃I CCl₂F₂ CBrClF₂ CClF₂I CBr₂F₂ CBrF₂I CF₂I₂ CCl₃F CBrCl₂F CCl₂FI CBr₂ClF C*BrClFI CClFI₂ CBr₃F CBr₂FI CBrFI₂ CFI₃ CCl₄ CBrCl₃ CCl₃I CBr₂Cl₂ CBrCl₂I CCl₂I₂ CBr₃Cl CBr₂ClI CBrClI₂ CClI₃ CBr₄ CBr₃I CBr₂I₂ CBrI₃ CI₄ CAt₄
* Chiral compound.

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案内

iodoform