tert-Butyl hydroperoxide

• Catalog No.: A13926
• CAS Number: 75-91-2
• M. F.: C4H10O2
• M. W.: 90.121
• Purity: 70% aq. soln.

SYNONYMS

• Title: 叔丁基过氧化氢
• IUPAC name: 2-methylpropane-2-peroxol
• IUPAC Traditional name: tert-butyl hydroperoxide
• Synonyms: TBHP

DATABASE IDS

• Beilstein Number: 1098280
• EC Number: 200-915-7
• Merck Index: 141570
• CAS Number: 75-91-2
• MDL Number: MFCD00002130

PROPERTIES

• Purity: 70% aq. soln.
• Boiling Point: 96°C dec.
• Density: 0.937
• Flash Point: 43°C(109°F)
• Melting Point: -3°C
• Refractive Index: 1.3870
• GHS Hazard statements: H311-H331-H302-H314-H318-H226-H242-H402-H412
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Oxidising (O)
• GHS Precautionary statements: P280-P235-P305+P351+P338-P309-P310-P420B
• Risk Statements: 7-10-20/21/22-34-52/53
• RTECS: EQ4900000
• Safety Statements: 3/7-26-36/37/39-45-61
• TSCA Listed: 是
• Hazard Class: 5.2
• UN Number: UN3109
• Packing Group: II

REFERENCES

• In combination with Mo(CO)₆ or Cr(CO)₆, oxidizes alkenes at allylic positions to give ɑ?-unsaturated ketones: J. Chem. Soc., Perkin 1, 267 (1985); Tetrahedron Lett., 25, 1235 (1984). Terminal alkynes are converted to methyl ketones in high yield in the presence of catalytic quantities of Pd(OAc)₂: J. Org. Chem., 45, 5387 (1980).
• In the presence of MoO₂(acac)₂, silyl enol ethers are cleaved in high yield, as an alternative to ozonolysis: Tetrahedron Lett., 22, 2595 (1981).
• In the presence of Dichlorotris(triphenylphosphine)ruthenium(II), L00373, secondary amines are dehydrogenated to imines: J. Chem. Soc., Chem. Commun., 613 (1985), and aryl or alkenyl cyanohydrins to acyl cyanides: Tetrahedron Lett., 26, 925 (1985).
• The anhydrous reagent can be prepared, e.g. in dilute toluene solution by azeotropic drying: method and safe handling procedure: J. Org. Chem., 48, 3607 (1983). See also: Chem. Ber., 113, 3662 (1980).
• Widely used in combination with various metal catalysts (Mo, Cr, V, W, Ti, etc.) for the epoxidation of alkenes. For a review of metal-catalyzed epoxidations, see: Chem. Rev., 89, 431 (1989).
• In the presence of Ti(O-i-Pr)₄ and (+)- or (-)-dialkyl tartrate, allylic alcohols undergo the Sharpless enantioselective epoxidation: J. Am. Chem. Soc., 102, 5974 (1980). The chirality of the major product is predictable and >95% ee is common:
  
• For reviews, see: Pure Appl. Chem., 55, 589 (1983); Synthesis, 89 (1986); Org. React., 48, 1 (1996). For an example, see: Org. Synth. Coll., 7, 461 (1990).