ChemicalBook CAS DataBase List 3376-24-7

3376-24-7

Name	N-TERT-BUTYL-ALPHA-PHENYLNITRONE
CAS	3376-24-7
EINECS(EC#)	222-168-6
Molecular Formula	C11H15NO
MDL Number	MFCD00008799
Molecular Weight	177.24
MOL File	3376-24-7.mol

Synonyms

BENZYLIDENE(TERT-BUTYL)AMMONIUMOLATE N-BENZYLIDENE-TERT-BUTYLAMINE N-OXIDE N-T-BUTYL-ALPHA-PHENYLNITRONE N-TERT-BUTYL-ALPHA-PHENYLNITRONE N-TERT-BUTYL-A-PHENYLNITRONE PBN PHENYL N-TERT-BUTYLNITRONE 2-methyl-n-(phenylmethylene)-2-propanaminn-oxide 2-methyl-n-(phenylmethylene)-s-propanaminen-oxide 2-methyl-n-(phenylmethylene)-s-propanaminn-oxide 2-phenyl-n-tert-butylnitrone alpha-phenyl-n-tert-butylnitrone Benzylidene(tert-butyl)azane oxide benzylidene-tert-butylaminen-oxide c-phenyl-n-tert-butylnitrone n-benzylidene-tert-butylamineoxide n-tert-butyl-2-phenylnitrone n-tert-butyl-alpha-phenyl-nitron n-tert-butyl-c-phenylnitrone N-tert-Butyl-α-phenylnitrone

Chemical Properties

Appearance	white to light beige fine crystalline powder
Melting point	73-74 °C(lit.)
Boiling point	283℃
density	0.990
refractive index	1.5480 (estimate)
Fp	119℃
storage temp.	2-8°C
solubility	DMSO: soluble
form	powder
pka	1.50±0.53(Predicted)
color	white
Water Solubility	Soluble in DMSO (10 mg/ml), chloroform (50 mg/ml), and water (20 mg/ml).
Detection Methods	HPLC
Merck	14,7056
BRN	2044028
Cosmetics Ingredients Functions	ANTIOXIDANT
InChI	1S/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3/b12-9-
InChIKey	IYSYLWYGCWTJSG-XFXZXTDPSA-N
SMILES	CC(C)(C)[N+](\[O-])=C\c1ccccc1
CAS DataBase Reference	3376-24-7(CAS DataBase Reference)
EPA Substance Registry System	2-Propanamine, 2-methyl-N-(phenylmethylene)-, N-oxide (3376-24-7)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302
Precautionary statements	P280-P305+P351+P338
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
RTECS	TX1760000
F	10
TSCA	Yes
HS Code	29299090
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

Chemical Properties

white to light beige fine crystalline powder

Uses

N-tert-Butyl-α-phenylnitrone has been used:

as a component of Dneasy Blood&Tissue buffer to preserve the oxidized state of DNA extracted from human non-tumorigenic epithelial breast (MCF10A) cells
as a free radical scavenger of reactive oxygen species (ROS) in microglial (MG) cell lines
to attenuate fibroblast senescence in unstable oral squamous cell carcinomas (GU-OSCC)

Uses

N-tert-Butyl-a-phenylnitrone is a commonly-used free radical trap. It contains radical scavenging activity and an ability to inhibit Cox-2 (cyclooxygenase-2). N-tert-Butyl-a-phenylnitrone is an antioxidant that has been shown to act as a protective agent in several experimental models of neurodegenerative disorders. N-tert-Butyl-a-phenylnitrone inhibits lipid peroxidation in rat liver microsomes. It also prevents the induction of inducible nitric oxide synthase (iNOS) by reactive oxygen species.

Uses

Spin trap reagent for carbon- or oxygen- or nitrogen-centered free radicals.

Synthesis Reference(s)

Tetrahedron, 48, p. 8677, 1992 DOI: 10.1016/S0040-4020(01)89443-6

General Description

Most commonly-used free radical trap. An antioxidant that has been shown to act as a protective agent in several experimental models of neurodegenerative disorders. Inhibits lipid peroxidation in rat liver microsomes. Also prevents the induction of inducible nitric oxide synthase (iNOS) by reactive oxygen species.

Biochem/physiol Actions

Product does not compete with ATP.

Purification Methods

Crystallise PBN from hexane. It is a free radical trap. [cf Janzen Methods Enzymology 105 188 1984, Beilstein 7 IV 519.]

Spectrum Detail

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