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tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.^[3] It is normally supplied as a 69–70% aqueous solution.

Application

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

Synthesis and production

Many synthetic routes are available, including:^[4]

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. ^[5]

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,^[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.^[7]^[8]

References

^ "IUPAC Complete Draft 2004" (PDF).
^ Cameo Chemicals, reference for NFPA values.
^ tert-butyl hydroperoxide at Organic Chemistry Portal
^ Jose Sanchez; Terry N. Myers. "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01.
^ Sigma Aldrich MSDS
^ "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
^ tert-BUTYL HYDROPEROXIDE at Chemicalland21
^ tert-Butyl hydroperoxide at http://environmentalchemistry.com

UpToDate Contents

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English Journal

Small Molecules that Protect Mitochondrial Function from Metabolic Stress Decelerate Loss of Photoreceptor Cells in Murine Retinal Degeneration Models.

Beeson C1,2, Lindsey C3,4, Nasarre C5, Bandyopadhyay M6, Perron N7, Rohrer B8,9.
Advances in experimental medicine and biology.Adv Exp Med Biol.2016;854:449-54. doi: 10.1007/978-3-319-17121-0_60.
One feature common to many of the pathways implicated in retinal degeneration is increased metabolic stress leading to impaired mitochondrial function. We found that exposure of cells to calcium ionophores or oxidants as metabolic stressors diminish maximal mitochondrial capacity. A library of 50,00
PMID 26427445

Diamide accelerates opening of the Tl+-induced permeability transition pore in Ca2+-loaded rat liver mitochondria.

Korotkov SM1, Konovalova SA2, Brailovskaya IV2.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2015 Oct 28. pii: S0006-291X(15)30792-0. doi: 10.1016/j.bbrc.2015.10.091. [Epub ahead of print]
Opening of the mitochondrial permeability transition pore (MPTP) in the inner membrane is due to matrix Ca2+ overload and matrix glutathione loss. Fixing the 'm' conformation of the adenine nucleotide translocase (ANT) by ADP or N-ethylmaleimide (NEM) inhibits opening of the MPTP. Oxidants (diamide
PMID 26518646

H2O2-Activated Mitochondrial Phospholipase iPLA2γ Prevents Lipotoxic Oxidative Stress in Synergy with UCP2, Amplifies Signaling via G-Protein-Coupled Receptor GPR40, and Regulates Insulin Secretion in Pancreatic β-Cells.

Ježek J1, Dlasková A1, Zelenka J1, Jabůrek M1, Ježek P1.
Antioxidants & redox signaling.Antioxid Redox Signal.2015 Oct 20;23(12):958-72. doi: 10.1089/ars.2014.6195. Epub 2015 May 21.
AIMS: Pancreatic β-cell chronic lipotoxicity evolves from acute free fatty acid (FA)-mediated oxidative stress, unprotected by antioxidant mechanisms. Since mitochondrial uncoupling protein-2 (UCP2) plays antioxidant and insulin-regulating roles in pancreatic β-cells, we tested our hypothesis, tha
PMID 25925080

Japanese Journal

The Anti-apoptotic Action of 5-Hydroxyindole: Protection of Mitochondrial Integrity

Bae Sung Jin,Lee Jun Sik,Lee Eun Kyeong [他],Kim Ji Min,Choi Jehun,Heo Hyoung-Sam,Yu Byung Pal,Chung Hae Young
Biological and Pharmaceutical Bulletin 33(4), 550-555, 2010
… Here, we tested whether 5HI protects against tert-butylhydroperoxide (t-BHP)-induced oxidative damage and mitochondrial dysfunction in human fibroblast cells. …
NAID 130000247997

A New Diarylheptanoid Glycoside from the Stem Bark of Alnus hirsuta and Protective Effects of Diarylheptanoid Derivatives in Human HepG2 Cells

Park Daae,Kim Hyoung Ja,Jung Seo Yun [他],Yook Chang-Soo,Jin Changbae,Lee Yong Sup
Chemical and Pharmaceutical Bulletin 58(2), 238-241, 2010
… Isolates were assessed for their hepatoprotective effects against tert-butylhydroperoxide (t-BHP)-induced toxicity in HepG2 cells. …
NAID 130000161600

Preventive Effect of Trimidox on Oxidative Stress in U937 Cell Line(Pharmacology)

Kanno Syu-ichi,Kakuta Mai,Kitajima Yasue [他],OSANAI Yuu,KURAUCHI Kaori,OHTAKE Takaharu,UJIBE Mayuko,UWAI Kouji,TAKESHITA Mitsuhiro,ISHIKAWA Masaaki
Biological & pharmaceutical bulletin 30(5), 994-998, 2007-05-01
… We have examined the effect of trimidox on the induction of cytotoxicity and apoptosis via oxidative stress by typical free radical inducers, hydrogen peroxide (H_2O_2), tert-butylhydroperoxide (tBuOOH) or ultraviolet (UV) irradiation in a human diffuse histiocytic lymphoma U937 cell line. …
NAID 110006273305

Related Pictures

★リンクテーブル★

リンク元	「tert-ブチルヒドロペルオキシド」

「tert-ブチルヒドロペルオキシド」

*tert*-Butyl hydroperoxide
Names
	Preferred IUPAC name 2-Methylpropane-2-peroxol
	Systematic IUPAC name tert-Butyl hydroperoxide
Identifiers
CAS Number	75-91-2
Abbreviations	TBHP
Beilstein Reference	1098280
ChEMBL	ChEMBL348399
ChemSpider	6170
EC Number	200-915-7
Jmol 3D model	Interactive image
MeSH	tert-Butylhydroperoxide
PubChem	6410
RTECS number	EQ4900000
UNII	955VYL842B
UN number	3109
	InChI InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 Key: CIHOLLKRGTVIJN-UHFFFAOYSA-N ;
	SMILES CC(C)(C)OO ;
Properties
Chemical 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
Thermochemistry
Std enthalpy of; formation (ΔfHo298)	−294±5 kJ/mol
Std enthalpy of; combustion (ΔcHo298)	2.710±0.005 MJ/mol
Hazards
Safety data sheet	[1]
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 (DSD)	O C T T+ F
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 OX
Flash point	43 °C (109 °F; 316 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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英: tert-butylhydroperoxide

[1] "IUPAC Complete Draft 2004" (PDF).

[Cameo_Chemicals-2] Cameo Chemicals, reference for NFPA values.

[3] tert-butyl hydroperoxide at Organic Chemistry Portal

[Kirk-Othmer-4] Jose Sanchez; Terry N. Myers. "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01.

[5] Sigma Aldrich MSDS

[6] "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA

[7] tert-BUTYL HYDROPEROXIDE at Chemicalland21

[8] tert-Butyl hydroperoxide at http://environmentalchemistry.com

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案内

tert-butylhydroperoxide