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19997

Sigma-Aldrich

tert-Butyl hydroperoxide solution

packed in FEP bottles, ~5.5 M in decane (over molecular sieve 4Å)

Synonym(s):

1,1-Dimethylethyl hydroperoxide, 2-Hydroperoxy-2-methylpropane, TBHP

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About This Item

Linear Formula:
(CH3)3COOH
CAS Number:
75-91-2
Molecular Weight:
90.12
Beilstein/REAXYS Number:
1098280
MDL number:
MFCD00002130
UNSPSC Code:
12162002
PubChem Substance ID:
57647815
NACRES:
NA.23

form

liquid

quality

packed in FEP bottles

reaction suitability

reagent type: oxidant

concentration

52.9-66.8% (iodometric)
~5.5 M in decane (over molecular sieve 4Å)

refractive index

n20/D 1.403

density

0.83 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

CC(C)(C)OO

InChI

1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3

InChI key

CIHOLLKRGTVIJN-UHFFFAOYSA-N

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Application

Used in oxidative desulfurization of fuelsand as an oxidant for the epoxidation of styrene.

Other Notes

Safe and stable oxidant for the Sharpless epoxidation

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 3 - Muta. 2 - Org. Perox. F - Skin Corr. 1C - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

109.4 °F - closed cup

flash_point_c

43 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Oxidative desulfurization of fuel oil. Part I. Oxidation of dibenzothiphenes using tert-butyl hydroperoxide
Wang D,et al.
Applied Catalysis A: General, 253, 91-99 (2003)
Controlled synthesis of a- and c-Fe2O3 nanoparticles via thermolysis of PVA gels and studies on a-Fe2O3 catalyzed styrene epoxidation.
Bepari RA,et al.
Journal of Saudi Chemical Society (2014)
K. Akashi et al.
The Journal of Organic Chemistry, 43, 2063-2063 (1978)
Maxim O Ratnikov et al.
Journal of the American Chemical Society, 135(4), 1549-1557 (2013-01-10)
A general mechanism is proposed for transition metal-catalyzed oxidative Mannich reactions of N,N-dialkylanilines with tert-butyl hydroperoxide (TBHP) as the oxidant. The mechanism consists of a rate-determining single electron transfer (SET) that is uniform from 4-methoxy- to 4-cyano-N,N-dimethylanilines. The tert-butylperoxy radical
Yury Minko et al.
Nature protocols, 8(4), 749-754 (2013-03-23)
This protocol describes a new approach for the preparation of stereodefined trisubstituted chiral enolate species, avoiding conventional asymmetric enolization of carbonyl compounds. This protocol was developed as a single-flask synthetic sequence and therefore does not require isolation or purification of
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