Pentafluoroethyl iodide
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428775889
| ImageFileL1 = Pentafluoroethyl-iodide-2D-skeletal.png
| ImageSizeL1 = 120px
| ImageFileR1 = Pentafluoroethyl-iodide-3D-vdW.png
| ImageSizeR1 = 120px
| PIN = Pentafluoro(iodo)ethane
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 354-64-3
| PubChem = 9636
| EINECS = 206-566-7
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 9259
| UNII = 0E13B713QU
| SMILES = C(C(F)(F)I)(F)(F)F
| InChI = 1/C2F5I/c3-1(4,5)2(6,7)8
| InChIKey = UXPOJVLZTPGWFX-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C2F5I/c3-1(4,5)2(6,7)8
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UXPOJVLZTPGWFX-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
| C=2 | F=5 | I=1
| Appearance = pungent colourless gas{{GESTIS|Name=Pentafluoriodethan|ZVG=491002|CAS=354-64-3|Date=2019-01-07}}
| Solubility =}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS04}}{{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|280|315|319|335|336}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|410+403|501}}
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Pentafluoroethyl iodide is a suggested component of a fire-extinguishing composition.US patent application 20010048094 It is a very dense gas.
Production
Pentafluoroethyl iodide can be produced by electrochemical fluorination of 1,1,2,2-tetrafluoro-1,2-diiodoethane.{{cite book| author=Bernd Baasner | title=Houben-Weyl Methods of Organic Chemistry Vol. E 10a, 4th Edition Supplement Organo-Fluorine Compounds - Fluorinating Agents and Their Application in Organic Synthesis | publisher=Georg Thieme Verlag | isbn=978-3-13-181544-6 | date=2014 | page=47,318}}
:{{chem2 | 2 C2F4I2 + 2 HF -> C2F5I + I2 + H2 }}
It can also be produced by react tetrafluoroethylene, iodine and iodine pentafluoride.{{cite book| author=R.E. Banks, B.E. Smart, J.C. Tatlow | title=Organofluorine Chemistry Principles and Commercial Applications | publisher=Springer Science & Business Media | isbn=978-1-4899-1202-2 | date=2013 | page=325}}
:{{chem2 | 5 C2F4 + 2 I2 + IF5 -> 5 C2F5I }}
Properties
Pentafluoroethyl iodide is a pungent colourless gas and an anesthetic.{{cite book| author=Maynard B. Chenoweth | title=Modern Inhalation Anesthetics | publisher=Springer Science & Business Media | isbn=978-3-642-65055-0 | date=2012 | page=424}}{{cite book| author=Ernst W. Alther | title=Pharmacology of Fluorides | publisher=Springer Science & Business Media | isbn=978-3-662-25198-0 | date=2013 | page=538}}
Uses
Pentafluoroethyl iodide is an intermediate of preparing other compounds.Google Patents: [https://patents.google.com/patent/US3351671 US3351671A - Preparation of pentafluoroiodoethane - Google Patents], retrieved 7 January 2019.{{cite book| author=Alexander Schönberg | title=Preparative Organic Photochemistry | publisher=Springer Science & Business Media | isbn=978-3-642-87918-0 | date=2012| page=174}}Google Patents: [https://patents.google.com/patent/US20080200735A1/en US20080200735A1 - Catalyst for the synthesis of CF3I and CF3CF2I - Google Patents], retrieved 7 January 2019.