tert-Butyl hydroperoxide

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tert-Butyl hydroperoxide
Skeletal formula of tert-butyl hydroperoxide
Identifiers
Abbreviations TBHP
CAS number 75-91-2 YesY
PubChem 6410
ChemSpider 6170 YesY
UNII 955VYL842B N
EC number 200-915-7
UN number 3109
MeSH tert-Butylhydroperoxide
ChEMBL CHEMBL348399 YesY
RTECS number EQ4900000
Beilstein Reference 1098280
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water miscible
log P 1.23
Acidity (pKa) 12.69
Basicity (pKb) 1.31
Refractive index (nD) 1.3870
Hazards
MSDS msds.chem.ox.ac.uk
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H226, H242, H302, H311, H314, H317, H331, H341, H411
GHS precautionary statements P220, P261, P273, P280, P305+351+338, P310
EU classification Oxidizing Agent O Corrosive C
R-phrases R7, R10, R20/21/22, R34, R43 R52/53
S-phrases S3/7, S14, S16, S17, S24, S36/37/39, S45, S61
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazard OX: Oxidizer. E.g., potassium perchlorateNFPA 704 four-colored diamond
Flash point 43 °C (109 °F; 316 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[3] It is normally supplied as a 69-70% aqueous solution.

Application[edit]

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

Synthesis and production[edit]

Many synthetic routes are available, including:[4]

Safety[edit]

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. It is also carcinogenic.[5]

A solution of Tert-butyl hydroperoxide and water with a concentration of greater than 90 percent 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,[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.[7][8]

See also[edit]

References[edit]

  1. ^ "IUPAC Complete Draft 2004". 
  2. ^ Cameo Chemicals, reference for NFPA values.
  3. ^ tert-butyl hydroperoxide at Organic Chemistry Portal
  4. ^ Jose Sanchez; Terry N. Myers. "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01. 
  5. ^ New Jersey MSDS
  6. ^ "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
  7. ^ tert-BUTYL HYDROPEROXIDE at Chemicalland21
  8. ^ tert-Butyl hydroperoxide at http://environmentalchemistry.com