2-phenylpropane-2-peroxol

• ChemBase ID: 110155
• Molecular Formular: C9H12O2
• Molecular Mass: 152.19038
• Monoisotopic Mass: 152.08372962
• SMILES: CC(C)(OO)c1ccccc1
• Canonical SMILES: OOC(c1ccccc1)(C)C
• InChI: InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
• InChIKey: YQHLDYVWEZKEOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenylpropane-2-peroxol
• IUPAC Traditional name: cumene hydroperoxide
• Synonyms: Cumyl Hydroperoxide; CHP; alpha,alpha-dimethylbenzyl hydroperoxide; CUMENE HYDROPEROXIDE; α,α-Dimethylbenzyl hydroperoxide; Cumene hydroperoxide; Cumene hydroperoxide (Luperox® CU90); Cumene hydroperoxide; 过氧化羟基异丙苯; α,α-二甲基苄基过氧化氢; 过氧化氢异丙苯; 过氧化氢异丙苯 (Luperox® CU90); 过氧化氢异丙苯

Database IDs

• CAS Number: 80-15-9
• EC Number: 201-254-7
• MDL Number: MFCD00002129
• Beilstein Number: 1908117
• PubChem SID: 24873686; 162095751; 24854872
• PubChem CID: 6629
• Chemspider ID: 6377
• Wikipedia Title: Cumene_hydroperoxide

CALCULATED PROPERTIES

• Acid pKa: 11.697564
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.352383
• LogD (pH = 7.4): 2.3523614
• Log P: 2.3523831
• Molar Refractivity: 43.2811 cm^3
• Polarizability: 17.155962 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1.5 g / 100 mL in water
• Apperance: colorless to pale yellow liquid
• Melting Point: -30°C; -40°C; -9°C
• Boiling Point: 100-101 °C/8 mmHg(lit.); 100-101 °C/8 mmHg(lit.); 100-102°C/8mm; 101 °C/8 mmHg; ca. 125 °C (decomposes, possibly explosively)
• Flash Point: 127.4 °F; 133 °F; 174.2 °F; 53 °C; 56°C(132°F); 57 °C; 57°C (134.6°F); 79 °C; 79 °C
• Density: 1.02 g/cm^3; 1.028 g/mL at 20 °C; 1.03 g/mL at 25 °C; 1.03 g/mL at 25 °C; 1.030; 1.038 g/mL at 25 °C
• Refractive Index: 1.5240; n20/D 1.519; n20/D 1.5210; n20/D 1.5230
• Vapor Pressure: <0.03 mmHg ( 20 °C); <0.03 mmHg ( 20 °C); 14 mmHg at 20 °C
• Vapor Density: 5.4 (vs air)

Safety Information

• RTECS: MX2450000
• European Hazard Symbols: Nature polluting (N); Oxidising (O); Toxic (T)
• UN Number: 3109; UN3109
• German water hazard class: 2; 3
• Hazard Class: 5.2
• Packing Group: II
• Risk Statements: 7-10-21/22-23-34-37-48/20/22-51/53-65; 7-21/22-23-34-48/20/22-51/53; R:7-21/22-23-34-48/20/22-51/53
• Safety Statements: 14.1-3/7-36/37/39-45-50-61; 3/7-14-26-36/37/39-45-61-62; 3/7-14-36/37/39-45-50-61; S:14-45-50-61-36/37/39-3/7
• 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:
  

  2

  1

  4
• GHS Hazard statements: 242, 302, 312, 314, 331, 373, 411; H226-H302-H304-H312-H314-H331-H335-H373-H411; H242-H302-H312-H314-H331-H373-H411; H331-H302-H312-H314-H226-H242-H373-H411
• GHS Precautionary statements: 220, 261, 273, 280, 305+351+338, 310; P210-P303+P361+P353-P305+P351+P338-P405-P410-P501A; P220-P261-P273-P280-P305 + P351 + P338-P310; P261-P273-P280-P301 + P310-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3109 5.2
• Storage Temperature: 2-8°C

Product Information

• Purity: 80%; 88%; tech. 80%
• Concentration: ~80% in cumene
• Grade: technical; technical grade
• Linear Formula: C6H5C(CH3)2OOH

DETAILS

Sigma Aldrich - 513296

Legal Information
Product of Arkema Inc.
Luperox is a registered trademark of Arkema Inc.

Sigma Aldrich - 247502

Packaging
5, 100, 500 g in poly bottle
Application
Epoxidation reagent for allylic alcohols1 and fatty acid esters,2 as an initiator for radical polymerization.3
Protocols & Applications
Asymmetric Epoxidation of Allylic Alcohols
Asymmetric Epoxidation of Homoallylic Alcohols
Asymmetric Ketone Hydrogenation
Asymmetric Transfer Hydrogenation

Sigma Aldrich - 28250

Other Notes
Sales restrictions may apply

REFERENCES

• Alternative to tert-Butyl hydroperoxide, A13926, in certain catalytic peroxygenation reactions. For example, has been found to give better enantiomeric excesses in the Sharpless-type asymmetric oxidation of sulfides to sulfoxides in the presence of Ti(O-i-Pr)₄ and diethyl L-tartrate: Tetrahedron, 43, 5135 (1987); Org. Synth. Coll., 8, 464 (1993); Synlett, 404 (1996).