Chloroiodomethane is the halomethane with the formula is CH 2ClI. It is a colorless liquid of use in organic synthesis.[1] Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.[2]
Chloroiodomethane is used in cyclopropanation (Simmon-Smith reaction), where it often replaces diiodomethane because of higher yields and selectivity. It is also used in Mannich reaction, aminomethylation, epoxidation, ring opening and addition to terminal alkenes. It is a precursor to agent Ph3P=CHCl that can add a chloromethylene group (=CHCl).[1] It reacts with organolithium compounds to give chloromethyl lithium (ClCH2Li).[3]
^ abMiyano, Sotaro; Friestad, Gregory K. (2008). "Chloroiodomethane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc110.pub2. ISBN978-0471936237.
^Fuse, Hiroyuki; Inoue, Hiroyuki; Murakami, Katsuji; Takimura, Osamu; Yamaoka, Yukiho (2003). "Production of free and organic iodine by Roseovarius spp.". FEMS Microbiology Letters. 229 (2): 189–94. doi:10.1016/S0378-1097(03)00839-5. PMID 14680698.
^Donald S. Matteson (2001). "Chloromethyllithium". EEROS. doi:10.1002/047084289X.rc117. ISBN0471936235.
^Torrie B. H.; Binbrek O. S.; von Dreele R. (1993). "Crystal structure of chloroiodomethane". Mol. Phys. 79 (4): 869–874(6). Bibcode:1993MolPh..79..869T. doi:10.1080/00268979300101691.
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chloroiodomethane, halomethane, with, formula, colorless, liquid, organic, synthesis, together, with, other, iodomethanes, chloroiodomethane, produced, some, microorganisms, names, preferred, iupac, name, chloro, iodo, methane, other, names, chloromethyl, iodi. Chloroiodomethane is the halomethane with the formula is CH2 ClI It is a colorless liquid of use in organic synthesis 1 Together with other iodomethanes chloroiodomethane is produced by some microorganisms 2 Chloroiodomethane Names Preferred IUPAC name Chloro iodo methane Other names ChloroiodomethaneChloroiodomethaneChloromethyl iodide Identifiers CAS Number 593 71 5 Y 3D model JSmol Interactive image Beilstein Reference 1730802 ChemSpider 11154 Y ECHA InfoCard 100 008 915 EC Number 209 804 8 PubChem CID 11644 UNII X7AF9WG7CX Y CompTox Dashboard EPA DTXSID50208034 InChI InChI 1S CH2ClI c2 1 3 h1H2 YKey PJGJQVRXEUVAFT UHFFFAOYSA N Y SMILES ClCI Properties Chemical formula C H 2Cl I Molar mass 176 38 g mol 1 Appearance Colorless liquid Density 2 422 g mL 1 Boiling point 108 to 109 C 226 to 228 F 381 to 382 K Henry s lawconstant kH 8 9 mmol Pa 1 kg 1 Refractive index nD 1 582 Hazards GHS labelling Pictograms Signal word Warning Hazard statements H315 H319 H335 Precautionary statements P261 P305 P351 P338 NFPA 704 fire diamond 110 Related compounds Related alkanes ChloromethaneBromochloromethaneDibromochloromethane Related compounds 2 Chloroethanol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Applications 2 Crystallography 3 References 4 External linksApplications editChloroiodomethane is used in cyclopropanation Simmon Smith reaction where it often replaces diiodomethane because of higher yields and selectivity It is also used in Mannich reaction aminomethylation epoxidation ring opening and addition to terminal alkenes It is a precursor to agent Ph3P CHCl that can add a chloromethylene group CHCl 1 It reacts with organolithium compounds to give chloromethyl lithium ClCH2Li 3 Crystallography editIt crystallizes orthorhombic crystal system with space group Pnma with lattice constants a 6 383 b 6 706 c 8 867 10 1 nm 4 References edit a b Miyano Sotaro Friestad Gregory K 2008 Chloroiodomethane E EROS Encyclopedia of Reagents for Organic Synthesis doi 10 1002 047084289X rc110 pub2 ISBN 978 0471936237 Fuse Hiroyuki Inoue Hiroyuki Murakami Katsuji Takimura Osamu Yamaoka Yukiho 2003 Production of free and organic iodine by Roseovarius spp FEMS Microbiology Letters 229 2 189 94 doi 10 1016 S0378 1097 03 00839 5 PMID 14680698 Donald S Matteson 2001 Chloromethyllithium EEROS doi 10 1002 047084289X rc117 ISBN 0471936235 Torrie B H Binbrek O S von Dreele R 1993 Crystal structure of chloroiodomethane Mol Phys 79 4 869 874 6 Bibcode 1993MolPh 79 869T doi 10 1080 00268979300101691 External links editUsage in organic synthesis nbsp This article about an organic halide is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Chloroiodomethane amp oldid 1146991250, wikipedia, wiki, book, books, library,
