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Fluoroiodomethane

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Fluoroiodomethane
Names

Preferred IUPAC name Fluoro(iodo)methane
Other names Fluoroiodomethane Fluoro-iodo-methane Fluoromethyl iodide
Identifiers
CAS Number	373-53-5^Y
3D model (JSmol)	Interactive image
ChemSpider	10329326^Y
ECHA InfoCard	100.201.539
PubChem CID	13981373
CompTox Dashboard(EPA)	DTXSID00553763
InChI InChI=1S/CH2FI/c2-1-3/h1H2^Y Key: XGVXNTVBGYLJIR-UHFFFAOYSA-N^Y 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 theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

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

Synthesis and uses

[edit]

It is prepared by fluorination ofmethylene iodide.^[1]

Itsisotopomer [¹⁸F]fluoroiodomethane is used for fluoromethylation ofradiopharmaceuticals.

Additional reading

[edit]

Zheng L.; Berridge M. S. (January 2000). "Synthesis of [¹⁸F]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. Archived fromthe original on December 10, 2012. Retrieved2007-06-29.
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

[edit]

^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.

Halomethanes

By substitution pattern

Unsubstituted

CH₄

Monosubstituted

Disubstituted

X,X	CH₂F₂ CH₂Cl₂ CH₂Br₂ CH₂I₂
X,Y	CH₂ClF CH₂BrF CH₂FI CH₂BrCl CH₂ClI CH₂BrI

Trisubstituted

X,X,X	CHF₃ CHCl₃ CHBr₃ CHI₃
X,X,Y	CHClF₂ CHBrF₂ CHF₂I CHCl₂F CHBr₂F CHFI₂ CHBrCl₂ CHCl₂I CHBr₂Cl CHClI₂ CHBr₂I CHBrI₂
X,Y,Z	CHBrClF CHClFI CHBrFI CHBrClI

Tetrasubstituted

X,X,X,X	CF₄ CCl₄ CBr₄ CI₄
X,X,X,Y	CFI₃ CClF₃ CBrF₃ CF₃I CCl₃F CBr₃F CBrCl₃ CCl₃I CBr₃Cl CClI₃ CBr₃I CBrI₃
X,X,Y,Y	CCl₂F₂ CBr₂F₂ CF₂I₂ CBr₂Cl₂ CCl₂I₂ CBr₂I₂
X,X,Y,Z	CBrClF₂ CClF₂I CBrF₂I CBrCl₂F CCl₂FI CBr₂ClF CClFI₂ CBr₂FI CBrFI₂ CBrCl₂I CBr₂ClI CBrClI₂
X,Y,Z,W	CBrClFI

Special types

Chiral

Isotopologues

C²H₂Cl₂ (CD₂Cl₂)
C²HCl₃ (CDCl₃)
C²H₃I (CD₃I)

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