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Tert-Butyl hydroperoxide

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
Systematic IUPAC name
tert-Butyl hydroperoxide
Identifiers
3D model (Jmol)
Abbreviations TBHP
1098280
ChemSpider
ECHA InfoCard 100.000.833
EC Number 200-915-7
MeSH tert-Butylhydroperoxide
PubChem CID
RTECS number EQ4900000
UNII
UN number 3109
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
Hazards
Safety data sheet [1]
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) The flame-over-circle pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H226, H242, H302, H311, H314, H317, H331, H341, H411
P220, P261, P273, P280, P305+351+338, P310
Oxidizing Agent O Corrosive C Toxic T Very Toxic T+ Highly Flammable F
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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. It is normally supplied as a 69–70% aqueous solution.

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

Many synthetic routes are available, including:

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.

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, however other sources claim lower ratings of 3-2-2 or 1-4-4.


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