Iodoacetone
{{Chembox
| ImageFile = Iodoacetone.svg
| ImageSize = 200px
| ImageAlt =
| PIN = 1-Iodopropan-2-one
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 3019-04-3
| PubChem = 76396
| ChemSpiderID = 68871
| EINECS = 221-161-5
| SMILES = CC(=O)CI
| StdInChI=1S/C3H5IO/c1-3(5)2-4/h2H2,1H3
| StdInChIKey= WEFSXBPMNKAUDL-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=3|H=5|I=1|O=1
| Appearance = Yellow liquid
| Density = 2.0±0.1 g/cm3
| Solubility =
| MeltingPt =
| BoilingPtC = 163.1
| VaporPressure = 2.1±0.3 mmHg
}}
| Section3 = {{Chembox Hazards
| MainHazards =
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| FlashPtC =
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Iodoacetone is an organoiodine compound with the chemical formula {{chem|C|3|H|5|I|O}}{{cite web|title=1-iodoacetone|url=http://www.chemsynthesis.com/base/chemical-structure-8178.html|publisher=chemsynthesis.com|access-date=1 June 2017}}{{cite journal|last1=Solly|first1=R.K.|last2=Golden|first2=D.M.|last3=Benson|first3=S.W.|title=Thermochemical properties of iodoacetone. Intramolecular electrostatic interactions in polar molecules|journal=J. Am. Chem. Soc.|date=1970|volume=92|issue=15|pages=4653–4656|url=http://webbook.nist.gov/cgi/cbook.cgi?Source=1970SOL%2FGOL4653-4656&Mask=1A8F|doi=10.1021/ja00718a030}} The substance is a colorless liquid{{Cite web|url=http://web.mnstate.edu/marasing/chem210l_2013_summer/iodination%20lab%20report1.pdf|title=Rate and Activation Energy of the Iodination of Acetone|last=Meyer|first=Earl|date=2010|website=|archive-url=|archive-date=|access-date=}} under normal conditions, soluble in ethanol.{{cite web|title=Properties of substance: iodoacetone|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=9502|publisher=chemister.ru|access-date=1 June 2017}}{{cite book|title=CRC Handbook of Chemistry and Physics|date=2010|publisher=CRC Press|pages=5–23|edition=90}}
Synthesis
The reaction of acetone and iodine produces iodoacetone. The reaction is typically acid catalysed and first order with respect to acetone and the acid catalyst:{{cite web|title=1-iodoacetone|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C3019043&Mask=1A8F|publisher=webbook.nist.gov|access-date=1 June 2017}}
:{{chem2|C3H6O + I2 -> HI + C3H5IO}}
See also
References
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