tert-Butyl hydroperoxide

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tert-Butyl hydroperoxide
Skeletal formula of tert-butyl hydroperoxide
Ball-and-stick model of the tert-butyl hydroperoxide molecule
Names
Preferred IUPAC name
2-Methylpropane-2-peroxol[1]
Systematic IUPAC name
tert-Butyl hydroperoxide
Identifiers
75-91-2 YesY
Abbreviations TBHP
1098280
ChEMBL ChEMBL348399 YesY
ChemSpider 6170 YesY
EC Number 200-915-7
Jmol 3D model Interactive image
MeSH tert-Butylhydroperoxide
PubChem 6410
RTECS number EQ4900000
UNII 955VYL842B N
UN number 3109
  • InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 YesY
    Key: CIHOLLKRGTVIJN-UHFFFAOYSA-N YesY
  • CC(C)(C)OO
Properties
C4H10O2
Molar mass 90.12 g·mol−1
Appearance Colorless liquid
Density 0.935 g/mL
Melting point −3 °C (27 °F; 270 K)
Boiling point 37 °C (99 °F; 310 K) at 2.0 kPa
miscible
log P 1.23
Acidity (pKa) 12.69
Basicity (pKb) 1.31
1.3870
Thermochemistry
−294±5 kJ/mol
2.710±0.005 MJ/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[2] It is normally supplied as a 69–70% aqueous solution.

Application

Industrially, tert-butyl hydroperoxide is used as a radical polymerization initiator.

Synthesis and production

Many synthetic routes are available, including:[3]

Safety

tert-butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. [4]

A solution of tert-butyl hydroperoxide and water with a concentration of greater than 90% is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172.101.

In some sources it also has an NFPA 704 rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant,[5] however other sources claim lower ratings of 3-2-2 or 1-4-4.[6][7]

See also

References

  1. Lua error in package.lua at line 80: module 'strict' not found.
  2. tert-butyl hydroperoxide at Organic Chemistry Portal
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. Sigma Aldrich MSDS
  5. "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
  6. tert-BUTYL HYDROPEROXIDE at Chemicalland21
  7. tert-Butyl hydroperoxide at http://environmentalchemistry.com