2-methylpropane-2-peroxol

• ChemBase ID: 105404
• Molecular Formular: C4H10O2
• Molecular Mass: 90.121
• Monoisotopic Mass: 90.06807956
• SMILES: CC(C)(C)OO
• Canonical SMILES: OOC(C)(C)C
• InChI: InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
• InChIKey: CIHOLLKRGTVIJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylpropane-2-peroxol
• IUPAC Systematic name: 2-Methylpropane-2-peroxol
• IUPAC Traditional name: tert-butyl hydroperoxide
• Synonyms: tert-Butyl hydroperoxide solution; Luperox® TBH70X, tert-Butyl hydroperoxide solution; Cadox TBH; Hydroperoxyde de Butyle Tertiaire; tert-Bytyl hydroperoxide; 1,1-Dimethylethyl hydroperoxide; Perbutyl H; terc. Butylhydroperoxid; t-BUTYL HYDROPEROXIDE 70% SOLUTION; Tert-Butyl hydroperoxide; 2-Hydroperoxy-2-methylpropane; TBHP; tert-Butyl hydroperoxide solution; tert-Butyl hydroperoxide; 叔丁基过氧化氢 溶液; Luperox® TBH70X, 叔丁基过氧化氢 溶液; 叔丁基过氧化氢 溶液; 叔丁基过氧化氢

Database IDs

• CAS Number: 75-91-2
• EC Number: 200-915-7
• MDL Number: MFCD00002130
• Beilstein Number: 1098280
• Merck Index: 141570
• PubChem SID: 24865918; 24851951; 24851948; 24851944; 24866199; 162092551; 24869433
• PubChem CID: 6410
• CHEMBL: 348399
• Chemspider ID: 6170
• MeSH Name: tert-Butylhydroperoxide
• Unique Ingredient Identifier: 955VYL842B
• Wikipedia Title: Tert-Butyl_hydroperoxide

CALCULATED PROPERTIES

• Acid pKa: 11.71938
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.98471767
• LogD (pH = 7.4): 0.9846972
• Log P: 0.98471797
• Molar Refractivity: 23.4171 cm^3
• Polarizability: 9.428219 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: miscible in water
• Apperance: Colourless liquid
• Melting Point: -3°C; -3°C; -34°C
• Boiling Point: 37°C (at 2.0 kPa); 96 °C; 96.2 °C; 96°C dec.
• Flash Point: 107.6 °F; 109.4 °F; 29 °C; 42 °C; 43 °C (closed cup); 43 °C; 43°C(109°F); 84.2 °F
• Auto Ignition Point: 238 °C
• Density: 0.808 g/mL at 25 °C; 0.817 g/mL at 25 °C; 0.82 g/mL at 20 °C; 0.83 g/mL at 20 °C; 0.90 g/mL at 20 °C; 0.93 g/mL at 25 °C; 0.937; 0.937 g/mL at 20 °C; 0.94 g/mL at 25 °C(lit.); 935 - 964 kg/m3 at 25 °C; 935 mg cm^-3
• Refractive Index: 1.3870; n20/D 1.386; n20/D 1.387; n20/D 1.397; n20/D 1.399; n20/D 1.400; n20/D 1.402; n20/D 1.403
• Vapor Pressure: ca. 30.7 hPa at 21 °C
• Partition Coefficient: 1.23
• pKa: 12.69
• pKb: 1.31
• Std enthalpy of combustion: 2.705-2.715 MJ mol^-1
• Std enthalpy of formation: -299–-289 kJ mol^-1

Safety Information

• Storage Condition: 2-8°C
• RTECS: EQ4900000
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N); Oxidising (O); Toxic (T); X; Harmful (Xn)
• UN Number: 3103; 3105; 3109; UN3109
• German water hazard class: 3
• Hazard Class: 5.2
• Packing Group: II
• Australian Hazchem: 2W
• Risk Statements: 7-10-20/21/22-34-52/53; 7-10-21/22-23-34-43-51/53-65-68; 7-10-21/22-23-34-43-51/53-68; R:7-10-18-20/21/22-34; R7, R10, R20/21/22, R34, R43 R52/53
• Safety Statements: 3/7-14-26-36/37/39-45-47-61; 3/7-14-26-36/37/39-45-61; 3/7-14-26-36/37/39-45-61-62; 3/7-17-26-36/37/39-43-45-47-61; 3/7-17-26-36/37/39-43-45-61; 3/7-17-26-36/37/39-45-61; 3/7-26-36/37/39-45-61; S:7-3/9/14-16-36/37/39; S3/7, S14, S16, S17, S24, S36/37/39, S45, S61
• EU Classification: P1
• EU Hazard Identification Number: 5.2
• Emergency Response Guidebook(ERG) Number: 145
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS environment; GHS flame; GHS health hazard; GHS skull and crossbones; GHS02; GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  4

  4

  4

  OX
• GHS Hazard statements: 226, 242, 302, 311, 314, 317, 331, 341, 411; H226-H242-H302-H304-H311 + H331-H314-H317-H336-H341-H411; H226-H242-H302-H304-H311 + H331-H314-H317-H341-H411; H226-H242-H302-H311-H314-H317-H330-H341-H411; H226-H242-H302-H311-H314-H317-H331-H341-H411; H226-H302-H304-H311 + H331-H314-H317-H336-H341-H411; H226-H302-H304-H311 + H331-H314-H317-H341-H411; H311-H331-H302-H314-H318-H226-H242-H402-H412
• GHS Precautionary statements: 220, 261, 273, 280, 305+351+338, 310; P220-P260-P273-P280-P284-P305 + P351 + P338; P220-P261-P273-P280-P301 + P310-P305 + P351 + P338; P220-P261-P273-P280-P305 + P351 + P338-P310; P261-P273-P280-P301 + P310-P305 + P351 + P338-P310; P280-P235-P305+P351+P338-P309-P310-P420B
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3103 5.2; UN 3105 5.2; UN 3109 5.2
• Storage Temperature: 2-8°C

Product Information

• Purity: 70% aq. soln.
• Concentration: ~5.5 M in decane (over molecular sieve 4Å); ~5.5 M in nonane (over molecular sieve 4 Å); ~70% in H2O; ~80% in di-tert-butyl peroxide/water 3:2; 5.0-6.0 M in decane; 5.0-6.0 M in nonane; 70 wt. % in H2O; 70% in H2O
• Grade: CP; purum
• Impurities: <4% water
• Quality: packed in FEP bottles
• Linear Formula: (CH3)3COOH

DETAILS

MP Biomedicals - 02190049

70% Aqueous solution
1 ml = approx. 0.93 g

Sigma Aldrich - 418064

Packaging
50 mL in poly bottle
Protocols & Applications
Asymmetric Epoxidation of Allylic Alcohols
Asymmetric Epoxidation of Homoallylic Alcohols
Asymmetric Ketone Hydrogenation
Asymmetric Transfer Hydrogenation

Sigma Aldrich - 416665

Packaging
25, 100 mL in poly bottle

Sigma Aldrich - 19999

Other Notes
Safe and stable oxidant for the Sharpless epoxidation1,2Reactant also used as a redox initiator3 and oxidant4
Packaging
25, 100 mL in PFA/FEP bottle

Sigma Aldrich - 458139

Packaging
1, 4 L in poly bottle
18 L in poly drum
25, 100 mL in poly bottle
Legal Information
Product of Arkema Inc.
Luperox is a registered trademark of Arkema Inc.
Application
Versatile reagent for oxidations.1,2,3,4

Sigma Aldrich - 19997

Other Notes
Safe and stable oxidant for the Sharpless epoxidation1,2
Packaging
25, 100 mL in PFA/FEP bottle

Sigma Aldrich - 19990

Packaging
100, 500 mL in poly bottle

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).