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300721

Sigma-Aldrich

Di-tert-butyl nitroxide

technical grade, 90%

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About This Item

Linear Formula:
[(CH3)3C]2NO
CAS Number:
2406-25-9
Molecular Weight:
145.24
EC Number:
219-298-0
MDL number:
MFCD00008800
UNSPSC Code:
12352000
PubChem Substance ID:
24857936
NACRES:
NA.22

grade

technical grade

assay

90%

refractive index

n20/D 1.435 (lit.)

bp

74-75 °C/34 mmHg (lit.)

functional group

amine

storage temp.

2-8°C

SMILES string

CC(C)(C)N([O])C(C)(C)C

InChI

1S/C8H18NO/c1-7(2,3)9(10)8(4,5)6/h1-6H3

InChI key

CKJMHSMEPSUICM-UHFFFAOYSA-N

Application

Di-tert-butyl nitroxide (DTBN) can be used as:
  • An additive for the synthesis of N-sulfenylimines by oxidative coupling of amines and disulfides or thiols using a copper-based metal-organic framework (MOF) as a catalyst.[1]
  • An initiator in the controlled radical polymerization reactions.[2][3]
  • A reagent in the preparation of N-aroyl-o-aroyl-N-tert-butylhdroxylamines by reacting with aromatic acid chlorides.[4]

Reagent for the room-temperature oxidation of primary and secondary benzylamines to imines[5] and for the ESR study of Lewis acid centers in Zeolite X.[6]
Spin label. Has been used in localization of lipid microdomains and thermal phenomena in murine stratum corneum.

accessory

Product No.
Description
Pricing

pictograms

FlameExclamation mark
GHS02,GHS07

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

114.8 °F - closed cup

flash_point_c

46 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
08508JR
03530JF
01922EY
13302PZ
09216DO

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J Fuchs et al.
The Journal of investigative dermatology, 98(5), 713-719 (1992-05-01)
Electron paramagnetic resonance (EPR) is a spectroscopic technique that allows detection of paramagnetic compounds, e.g., free radicals, in skin, and is used for measuring skin membrane fluidity and polarity. EPR imaging is concerned with spatially resolved EPR spectroscopy. We studied
Heverton Silva Camargos et al.
Lipids, 45(5), 419-427 (2010-04-03)
In this work, we have used electron paramagnetic resonance (EPR) spectroscopy of the small spin label di-tert-butyl nitroxide (DTBN), which partitions the aqueous and hydrocarbon phases, to study the interaction of the terpenes alpha-terpineol, 1,8-cineole, L(-)-carvone and (+)-limonene with the
Direct synthesis of N-sulfenylimines through oxidative coupling of amines with disulfides/thiols over copper based metal-organic frameworks
Long, W, et al.
Royal Society of Chemistry Advances, 6(47), 40945-40952 (2016)
The Journal of Organic Chemistry, 50, 5382-5382 (1985)
Z. Chem., 25, 253-253 (1985)
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