| Revision as of 15:54, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 447704607 of page (Bis(trifluoroacetoxy)iodo)benzene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 05:30, 21 January 2023 edit DePiep (talk | contribs)Extended confirmed users294,285 edits long name, use SHY in title |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Chembox |
|
{{Chembox |
|
|
| Name=(Bis(trifluoroacetoxy)iodo){{SHY}}benzene |
| ⚫ |
| verifiedrevid = 447626668 |
|
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 477200856 |
|
| ImageFile1 = (bis(trifluoroacetoxy)iodo)benzene.png |
|
| ImageFile1 = (bis(trifluoroacetoxy)iodo)benzene.png |
|
| ImageSize1 = 150px |
|
| ImageSize1 = 150px |
|
| ImageFile2 = (bis(trifluoroacetoxy)iodo)benzene-3D-balls.png |
|
| ImageFile2 = (bis(trifluoroacetoxy)iodo)benzene-3D-balls.png |
|
| ImageSize2 = 150px |
|
| ImageSize2 = 150px |
|
|
| PIN = Phenyl-λ<sup>3</sup>-iodanediyl bis(trifluoroacetate) |
|
| IUPACName = |
|
|
| OtherNames = |
|
| OtherNames = Phenyliodine bis(trifluoroacetate); PIFA |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| InChI = 1/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H |
|
| InChI = 1/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H |
|
| InChIKey = PEZNEXFPRSOYPL-UHFFFAOYAA |
|
| InChIKey = PEZNEXFPRSOYPL-UHFFFAOYAA |
| Line 15: |
Line 17: |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = PEZNEXFPRSOYPL-UHFFFAOYSA-N |
|
| StdInChIKey = PEZNEXFPRSOYPL-UHFFFAOYSA-N |
|
|
| CASNo_Ref = {{cascite|changed|??}} |
|
| CASNo = <!-- blanked - oldvalue: 2712-78-9 --> |
|
|
|
| CASNo = 2712-78-9 |
|
| PubChem = 102317 |
|
| PubChem = 102317 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 92428 |
|
| ChemSpiderID = 92428 |
|
|
| EC_number = 220-308-0 |
|
|
| UNII = 659SFV27XS |
|
| SMILES = FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1 |
|
| SMILES = FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1 |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=10|H=5|F=6|I=1|O=4 |
|
| C=10 | H=5 | F=6 | I=1 | O=4 |
|
| Appearance = |
|
| Appearance = |
|
| Density = |
|
| Density = |
| Line 28: |
Line 33: |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = }} |
|
| Solubility = }} |
|
| Section3 = {{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards = |
|
| MainHazards = |
|
|
| GHSPictograms = {{GHS07}} |
|
|
| GHSSignalWord = Warning |
|
|
| HPhrases = {{H-phrases|315|319|335}} |
|
|
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = }} |
|
| AutoignitionPt = }} |
|
}} |
|
}} |
|
|
|
|
|
'''(Bis(trifluoroacetoxy)iodo)benzene''', {{chem|C|6|H|5|I(OCOCF|3|)|2}}, is a ] compound used as a reagent in ]. It can be used to carry out the ] under acidic conditions.<ref name = HA /> |
|
|
|
|
|
== Preparation == |
|
|
The syntheses of all aryl ] compounds start from ]. The compound can be prepared by reaction of iodobenzene with a mixture of ] and ] in a method analogous to the synthesis of {{nowrap|]:<ref name = HA />}} |
|
|
:] |
|
|
|
|
|
It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid:<ref name = OS /> |
|
|
:] |
|
|
|
|
|
== Uses == |
|
|
It also brings around the conversion of a ] to a ] compound, for example in the ]. It also converts ]s to their parent ] compounds. |
|
|
|
|
|
=== Hofmann rearrangement === |
|
|
The ] is a decarbonylation reaction whereby an ] is converted to an ] by way of an ] intermediate. It is usually carried out under strongly basic conditions.<ref>{{cite journal|first1 = Everett S.|last1 = Wallis|last2 = Lane|first2 = John F.|title = The Hofmann Reaction|journal = ]|year = 1946|volume = 3|issue = 7|pages = 267–306|doi = 10.1002/0471264180.or003.07}}</ref><ref>{{cite book|chapter = Hofmann Reaction|pages = 134–136|title = Name Reactions in Organic Chemistry|first = Alexander R.|last = Surrey|edition = 2nd|publisher = ]|year = 1961|isbn = 9781483258683|chapter-url = https://books.google.com/books?id=JSESBQAAQBAJ&pg=PA134}}</ref> |
|
|
::] |
|
|
|
|
|
The reaction can also be carried out under mildly acidic conditions by way of the same intermediate using a hypervalent iodine compound in aqueous solution.<ref name = HA>{{cite book|chapter = 6.15 Hofmann, Curtius, Schmidt, Lossen, and Related Reactions|first1 = Jeffrey|last1 = Aubé|first2 = Charlie|last2 = Fehl|first3 = Ruzhang|last3 = Liu|first4 = Michael C.|last4 = McLeod|first5 = Hashim F.|last5 = Motiwala|title = Heteroatom Manipulations|series = Comprehensive Organic Synthesis II|year = 1993|volume = 6|pages = 598–635|doi = 10.1016/B978-0-08-097742-3.00623-6|isbn = 9780080977430}}</ref> An example published in '']'' is the conversion of ], easily synthesized from ], to ].<ref name = OS /> The ] is initially present as its ] ], which can be converted to the ] to facilitate product purification.<ref name = HA /><ref name = OS>{{OrgSynth|last1 = Almond|first1 = M. R.|last2 = Stimmel|first2 = J. B.|last3 = Thompson|first3 = E. A.|last4 = Loudon|first4 = G. M.|page = 132|volume = 66|year = 1988|prep = cv8p0132 |title = Hofmann Rearrangement Under Mildly Acidic Conditions Using Iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide|doi = 10.15227/orgsyn.066.0132|collvol = 8|collvolpages = 132}}</ref> |
|
|
::] |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{DEFAULTSORT:Bis(trifluoroacetoxy)iodo)benzene}} |
|
|
] |
|
|
] |
|
|
] |
|
|
] |