Fluoroiodomethane: Difference between revisions

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	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~400094258~~		\| verifiedrevid = 442806496
	\| ImageFile = Fluoroiodomethane.~~png~~		\| ImageFile = Fluoroiodomethane Formula V1.svg
	\| ImageSize = 120px		\| ImageSize = 120px
			\| PIN = Fluoro(iodo)methane <!-- Parentheses are used according to Subsection P-16.5.1.3 of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
	\| IUPACName = Fluoroiodomethane
	\| OtherNames = Fluoro-iodo-methane, Fluoromethyl iodide		\| OtherNames = Fluoroiodomethane<br />Fluoro-iodo-methane<br />Fluoromethyl iodide
	\| Section1 = {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 10329326		\| ChemSpiderID = 10329326
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = XGVXNTVBGYLJIR-UHFFFAOYSA-N		\| StdInChIKey = XGVXNTVBGYLJIR-UHFFFAOYSA-N
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 373-53-5		\| CASNo = 373-53-5
	\| PubChem =		\| PubChem = 13981373
	\| SMILES = FCI		\| SMILES = FCI
	\| InChI = 1/CH2FI/c2-1-3/h1H2		\| InChI = 1/CH2FI/c2-1-3/h1H2
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = CH<sub>2</sub>FI		\| Formula = CH<sub>2</sub>FI
	\| MolarMass = 159.93 g/mol		\| MolarMass = 159.93 g/mol
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	\| Density =		\| Density =
	\| MeltingPt =		\| MeltingPt =
	\| ~~BoilingPt~~ = 53.4 °C		\| BoilingPtC = 53.4
	\| Solubility =		\| Solubility =
	}}		}}
	\| Section3 = {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards =		\| MainHazards =
	\| FlashPt =		\| FlashPt =
	\| ~~Autoignition~~ =		\| AutoignitionPt =
			\| GHSPictograms = {{GHS06}}
			\| GHSSignalWord = Danger
			\| HPhrases = {{H-phrases\|301\|311\|330}}
			\| PPhrases = {{P-phrases\|260\|264\|270\|271\|280\|284\|301+310\|302+352\|304+340\|310\|312\|320\|321\|322\|330\|361\|363\|403+233\|405\|501}}
	}}		}}
	}}		}}

	'''Fluoroiodomethane''' is ~~a mixed~~ ], ~~more~~ ~~exactly~~ ''fluoroiodocarbon'' (FIC).		'''Fluoroiodomethane''' is the ] with the formula FCH<sub>2</sub>I. Also classified as a fluoroiodocarbon (FIC), it is a colorless liquid. It is a ] for the introduction of the fluoromethyl (FCH<sub>2</sub>) group.

			==Synthesis and uses==
	Fluoroiodomethane can be prepared from ].<ref></ref>
			It is prepared by fluorination of ].<ref>{{cite encyclopedia\|chapter=Fluoroiodomethane\|last1=Landelle\|first1=Gregory\|title=Encyclopedia of Reagents for Organic Synthesis\|last2=Paquin\|first2=Jean-Francois\|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis\|year=2011\|doi=10.1002/047084289X.rn01273\|isbn=978-0471936237}}</ref>

	Its ] fluoroiodomethane ~~(] )~~ is ~~a synthetic precursor~~ for fluoromethylation of ].		Its ] fluoroiodomethane is used for fluoromethylation of ].

			==Additional reading==
	Also proposal of its use as a safe high-performance foam blowing agent exists.<ref></ref>
		⚫	*{{cite journal \|author1=Zheng L. \|author2=Berridge M. S. \| date = January 2000 \| title = Synthesis of [<sup>18</sup>F]fluoromethyl iodide, a synthetic precursor for fluoromethylation of radiopharmaceuticals \| journal = Applied Radiation and Isotopes \| volume = 52 \| issue = 1 \| pages = 55–61(7) \| pmid = 10670923 \| doi = 10.1016/S0969-8043(99)00061-5 }}
		⚫	*{{cite journal \|author1=Chin F. T. \|author2=Morse Ch. L. \|author3=Shetty H. U. \|author4=Pike V. W. \| date = December 2005 \| title = Automated radiosynthesis of [18F]SPA-RQ for imaging human brain NK1 receptors with PET \| journal = Journal of Labelled Compounds and Radiopharmaceuticals \| volume = 49 \| issue = 1 \| pages = 17–31(15) \| doi = 10.1002/jlcr.1016 \| url = http://www3.interscience.wiley.com/cgi-bin/abstract/112221807/ABSTRACT?CRETRY=1&SRETRY=0 \| access-date = 2007-06-29 }}{{dead link\|date=February 2019\|bot=medic}}{{cbignore\|bot=medic}}
		⚫	*{{cite journal \|author1=Tedder, J. M. \|author2=Sloan, J. P. \|author3=Walton, J. C. \| date = 1975 \| title = Free Radical Addition to Olefins, Part XVII. Addition of Fluoroiodomethane to Fluoroethylenes\| journal = Journal of the Chemical Society \| pages = 1846–1850 }}

	==~~Notes~~==		==References==
	{{reflist}}		{{reflist}}

	==References==
⚫	*{{cite journal \| ~~author~~ = Zheng L.; Berridge M. S. \| date = January 2000 \| title = Synthesis of [<sup>18</sup>F]fluoromethyl iodide, a synthetic precursor for fluoromethylation of radiopharmaceuticals \| journal = Applied Radiation and Isotopes \| volume = 52 \| issue = 1 \| pages = 55–61(7) \| pmid = 10670923 \| doi = 10.1016/S0969-8043(99)00061-5 ~~\| url = http://www.ingentaconnect.com/content/els/09698043/2000/00000052/00000001/art00061 \| accessdate = 2007-06-29~~ }}
⚫	*{{cite journal \| ~~author~~ = Chin F. T., Morse Ch. L., Shetty H. U., Pike V. W. \| date = December 2005 \| title = Automated radiosynthesis of [18F]SPA-RQ for imaging human brain NK1 receptors with PET \| journal = Journal of Labelled Compounds and Radiopharmaceuticals \| volume = 49 \| issue = 1 \| pages = 17–31(15) \| doi = 10.1002/jlcr.1016 \| url = http://www3.interscience.wiley.com/cgi-bin/abstract/112221807/ABSTRACT?CRETRY=1&SRETRY=0 \| ~~accessdate~~ = 2007-06-29 }}
⚫	*{{cite journal \| ~~author~~ = Tedder, J. M.; Sloan, J. P.; Walton, J. C. \| date = 1975 \| title = Free Radical Addition to Olefins, Part XVII. Addition of Fluoroiodomethane to Fluoroethylenes\| journal = Journal of the Chemical Society ~~\| volume = \| issue =~~ \| pages = 1846–1850 ~~\| pmid = \| doi = \| url = \| accessdate =~~ }}

	{{Halomethanes}}		{{Halomethanes}}
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	{{organohalide-stub}}		{{organohalide-stub}}

	]
	]
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Latest revision as of 15:55, 31 October 2021

Fluoroiodomethane
Names

Preferred IUPAC name Fluoro(iodo)methane
Other names Fluoroiodomethane Fluoro-iodo-methane Fluoromethyl iodide
Identifiers
CAS Number	373-53-5
3D model (JSmol)	Interactive image
ChemSpider	10329326
ECHA InfoCard	100.201.539
PubChem CID	13981373
CompTox Dashboard (EPA)	DTXSID00553763
InChI InChI=1S/CH2FI/c2-1-3/h1H2Key: XGVXNTVBGYLJIR-UHFFFAOYSA-N InChI=1/CH2FI/c2-1-3/h1H2
SMILES FCI
Properties
Chemical formula	CH₂FI
Molar mass	159.93 g/mol
Boiling point	53.4 °C (128.1 °F; 326.5 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H330
Precautionary statements	P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Fluoroiodomethane is the halomethane with the formula FCH₂I. Also classified as a fluoroiodocarbon (FIC), it is a colorless liquid. It is a reagent for the introduction of the fluoromethyl (FCH₂) group.

Synthesis and uses

It is prepared by fluorination of methylene iodide.

Its isotopomer fluoroiodomethane is used for fluoromethylation of radiopharmaceuticals.

Additional reading

Zheng L.; Berridge M. S. (January 2000). "Synthesis of [F]fluoromethyl iodide, a synthetic precursor for fluoromethylation of radiopharmaceuticals". Applied Radiation and Isotopes. 52 (1): 55–61(7). doi:10.1016/S0969-8043(99)00061-5. PMID 10670923.
Chin F. T.; Morse Ch. L.; Shetty H. U.; Pike V. W. (December 2005). "Automated radiosynthesis of [18F]SPA-RQ for imaging human brain NK1 receptors with PET". Journal of Labelled Compounds and Radiopharmaceuticals. 49 (1): 17–31(15). doi:10.1002/jlcr.1016. Retrieved 2007-06-29.
Tedder, J. M.; Sloan, J. P.; Walton, J. C. (1975). "Free Radical Addition to Olefins, Part XVII. Addition of Fluoroiodomethane to Fluoroethylenes". Journal of the Chemical Society: 1846–1850.

References

Landelle, Gregory; Paquin, Jean-Francois (2011). "Fluoroiodomethane". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01273. ISBN 978-0471936237.

v t e Halomethanes
Unsubstituted	CH₄
Monosubstituted	CH₃F CH₃Cl CH₃Br CH₃I CH₃At
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
* Chiral compound.

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