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| Names | |||
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Preferred IUPAC name
2-Methylpropane-2-peroxol
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Systematic IUPAC name
tert-Butyl hydroperoxide
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| Identifiers | |||
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3D model (Jmol)
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| Abbreviations | TBHP | ||
| 1098280 | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.833 | ||
| EC Number | 200-915-7 | ||
| MeSH | tert-Butylhydroperoxide | ||
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PubChem CID
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| RTECS number | EQ4900000 | ||
| UNII | |||
| UN number | 3109 | ||
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| 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 | ||
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Refractive index (nD)
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1.3870 | ||
| Thermochemistry | |||
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Std enthalpy of
formation (ΔfH |
−294±5 kJ/mol | ||
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Std enthalpy of
combustion (ΔcH |
2.710±0.005 MJ/mol | ||
| Hazards | |||
| Safety data sheet | [1] | ||
| GHS pictograms |
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| GHS signal word | DANGER | ||
| H226, H242, H302, H311, H314, H317, H331, H341, H411 | |||
| P220, P261, P273, P280, P305+351+338, P310 | |||
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EU classification (DSD)
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| 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 | |||
| Flash point | 43 °C (109 °F; 316 K) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.