Tert-butyl_hypochlorite

<i>tert</i>-Butyl hypochlorite

tert-Butyl hypochlorite

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).[1]

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Synthesis and reactions

It is produced by chlorination of tert-butyl alcohol in the presence of base:[2][3]

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

tert-Butyl hypochlorite is useful in the preparation of organic chloramines:[4]

R2NH + t-BuOCl → R2NCl + t-BuOH

References

  1. [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. [2]
    Teeter, H. M.; Bell, E. W. (1952). "tert-Butyl Hypochlorite". Org. Synth. 32: 20. doi:10.15227/orgsyn.032.0020.
  3. [3]
    Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.
  4. [4]
    Herranz, Eugenio; Sharpless, K. Barry (1983). "Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate". Org. Synth. 61: 93. doi:10.15227/orgsyn.061.0093.
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