Tert-Butyl hydroperoxide

tert-Butyl hydroperoxide
Preferred IUPAC name 2-Methylpropane-2-peroxol[1]
Systematic name tert-Butyl hydroperoxide
Identifiers
Abbreviations	TBHP
CAS number	75-91-2 Y
PubChem	6410
ChemSpider	6170 Y
UNII	955VYL842B N
EC number	200-915-7
UN number	3109
MeSH	tert-Butylhydroperoxide
ChEMBL	CHEMBL348399 Y
RTECS number	EQ4900000
Beilstein Reference	1098280
Jmol-3D images	Image 1
SMILES CC(C)(C)OO
InChI InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 Y Key: CIHOLLKRGTVIJN-UHFFFAOYSA-N Y
Properties
Molecular formula	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)
Solubility in water	miscible
log P	1.23
Acidity (pKa)	12.69
Basicity (pKb)	1.31
Refractive index (nD)	1.3870
Hazards
MSDS	msds.chem.ox.ac.uk
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H226, H242, H302, H311, H314, H317, H331, H341, H411
GHS precautionary statements	P220, P261, P273, P280, P305+351+338, P310
EU classification	O C
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	4 4 4
Flash point	43 °C; 109 °F; 316 K
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.^[2] It is normally supplied as a 69-70% aqueous solution.

Application

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

Synthesis and production

Many synthetic routes are available, including:^[3]

• Reaction of hydrogen peroxide with isobutylene or tert-butyl alcohol in the presence of sulfuric acid
• Reaction between tert-butyl alcohol and peroxymonosulfuric acid (however, an explosive intermediate is formed in this reaction)
• Auto-oxidation of isobutylene with oxygen

Safety

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. It is also carcinogenic.^[4]

A solution of Tert-butyl hydroperoxide and water with a concentration of greater than 90 percent 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,^[5] however other sources claim lower ratings of 3-2-2 or 1-4-4.^[6][7]

See also

• Organic peroxide
• Peroxy acid

References