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tert-Butyl hypochlorite

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tert-Butyl hypochlorite
Names
Preferred IUPAC name tert-Butyl hypochlorite
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.339 Edit this at Wikidata
EC Number
  • 208-072-7
PubChem CID
UNII
UN number 3255
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9ClO/c1-4(2,3)6-5/h1-3H3Key: IXZDIALLLMRYOU-UHFFFAOYSA-N
SMILES
  • ClOC(C)(C)C
Properties
Chemical formula C4H9ClO
Molar mass 108.57 g·mol
Appearance Yellow liquid
Density 0.9583 g/cm
Boiling point 79.6 °C (175.3 °F; 352.8 K) explosive
Solubility in water Sparingly
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS03: OxidizingGHS05: CorrosiveGHS08: Health hazard
Signal word Danger
Hazard statements H225, H250, H251, H271, H314, H334
Precautionary statements P210, P220, P221, P222, P233, P235+P410, P240, P241, P242, P243, P260, P261, P264, P280, P283, P285, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P306+P360, P310, P321, P342+P311, P363, P370+P378, P371+P380+P375, P403+P235, P405, P407, P413, P420, P422, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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).

Synthesis and reactions

It is produced by chlorination of tert-butyl alcohol in the presence of base:

(CH3)3COH + Cl2 + NaOH → (CH3)3COCl + NaCl + H2O

tert-Butyl hypochlorite is useful in the preparation of organic chloramines:

R2NH + t-BuOCl → R2NCl + t-BuOH

References

  1. Simpkins, Nigel S.; Cha, Jin K. (2006). "t-Butyl Hypochlorite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb388.pub2. ISBN 0471936235.
  2. Teeter, H. M.; Bell, E. W. (1952). "tert-Butyl Hypochlorite". Org. Synth. 32: 20. doi:10.15227/orgsyn.032.0020.
  3. Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.
  4. Herranz, Eugenio; Sharpless, K. Barry (1983). "Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-carbamate". Org. Synth. 61: 93. doi:10.15227/orgsyn.061.0093.
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