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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.
  • An initiator in the controlled radical polymerization reactions.
  • A reagent in the preparation of N-aroyl-o-aroyl-N-tert-butylhdroxylamines by reacting with aromatic acid chlorides.

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

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Nans Roques et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(21), 5547-5562 (2006-05-09)
Five bis(tert-butylnitroxide) diradicals connected by a silole (7 a-d) or a thiophene (12) ring as a coupler were studied. Compound 12 crystallizes in the orthorhombic space group Pna2(1) with a = 20.752(5), b = 5.826(5), and c = 34.309(5) A.
F Severcan et al.
Bioscience reports, 9(4), 489-495 (1989-08-01)
The effect of alpha-tocopherol (alpha T) on partitioning and fluidity changes occurring in phospholipid liposomes have been investigated by monitoring the X-band ESR spectrum of the high resolution amphiphilic spin probe perdeutero-di-t-butyl nitroxide (PDDTBN), which partitions in the lipid and
Sebastian Sinnecker et al.
The journal of physical chemistry. A, 110(6), 2235-2245 (2006-02-10)
The conductor-like screening model (COSMO) was used to investigate the solvent influence on electronic g-values of organic radicals. The previously studied diphenyl nitric oxide and di-tert-butyl nitric oxide radicals were taken as test cases. The calculations employed spin-unrestricted density functional
Living radical polymerization of styrene derivatives containing trialkylmetal groups
David-Quillot F, et al.
Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 47(5), 461-467 (2010)

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