Tert-Butyl hypochlorite
{{DISPLAYTITLE: tert-Butyl hypochlorite}}
{{Chembox
| Name = tert-Butyl hypochlorite
| ImageFile = TBuOCl.svg
| ImageSize = 144
| ImageAlt =
| PIN = tert-Butyl hypochlorite
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 507-40-4
| PubChem = 521297
| ChemSpiderID = 454718
| EINECS = 208-072-7
| UNNumber = 3255
| UNII = LS2JTI16JZ
| SMILES = ClOC(C)(C)C
| StdInChI=1S/C4H9ClO/c1-4(2,3)6-5/h1-3H3
| StdInChIKey = IXZDIALLLMRYOU-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=4|H=9|Cl=1|O=1
| MolarMass =
| Appearance = Yellow liquid
| Density = 0.9583 g/cm3
| MeltingPtC =
| BoilingPtC = 79.6
| BoilingPt_notes = explosive
| Solubility = Sparingly}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS03}}{{GHS05}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|250|251|271|314|334}}
| PPhrases = {{P-phrases|210|220|221|222|233|235+410|240|241|242|243|260|261|264|280|283|285|301+330+331|302+334|303+361+353|304+340|304+341|305+351+338|306+360|310|321|342+311|363|370+378|371+380+375|403+235|405|407|413|420|422|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =}}
}}
tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).{{cite book|doi=10.1002/047084289X.rb388.pub2|chapter=t-Butyl Hypochlorite|title=Encyclopedia of Reagents for Organic Synthesis|year=2006|last1=Simpkins|first1=Nigel S.|last2=Cha|first2=Jin K.|isbn=0471936235}}
Synthesis and reactions
It is produced by chlorination of tert-butyl alcohol in the presence of base:{{cite journal|title=tert-Butyl Hypochlorite
|first1=H. M.|last1=Teeter|first2=E. W.|last2=Bell|journal=Org. Synth.|year=1952|volume=32|page=20|doi=10.15227/orgsyn.032.0020}}{{cite journal|title=t-Butyl Hypochlorite
|first1=H. M.|last1=Mintz|first2=C.|last2=Walling|journal=Org. Synth.|year=1969|volume=49|page=9|doi=10.15227/orgsyn.049.0009}}
:{{chem2|(CH3)3COH + Cl2 + NaOH → (CH3)3COCl + NaCl + H2O}}
tert-Butyl hypochlorite is useful in the preparation of organic chloramines such as chloramine-T:{{cite journal|title=Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate|first1=Eugenio|last1=Herranz|first2=K. Barry|last2=Sharpless|journal=Org. Synth.|year=1983|volume=61|page=93|doi =10.15227/orgsyn.061.0093}}
:R2NH + t-BuOCl → R2NCl + t-BuOH
References
{{Reflist}}
{{DEFAULTSORT:Butyl hypochlorite, tert-}}