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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:
Molecular Weight:
145.24
EC Number:
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
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.

pictograms

FlameExclamation mark

signalword

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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S I Dikalov et al.
The Journal of biological chemistry, 274(14), 9392-9399 (1999-03-27)
Amyloid beta (Abeta) peptides play an important role in the pathogenesis of Alzheimer's disease. Free radical generation by Abeta peptides was suggested to be a key mechanism of their neurotoxicity. Reports that neurotoxic free radicals derived from Abeta-(1-40) and Abeta-(25-35)
J A Kenar et al.
Chemical research in toxicology, 9(4), 737-744 (1996-06-01)
Oxidation of human LDL is implicated as an initiator of atherosclerosis. Isolated low density lipoprotein (LDL) and high density lipoprotein (HDL2) were exposed to aqueous radicals generated from the thermolabile azo compound 2,2'-azobis(2-amidinopropane) dihydrochloride. The primary nonpolar lipid products formed
Z. Chem., 25, 253-253 (1985)
The Journal of Organic Chemistry, 50, 5382-5382 (1985)
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)

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