N-tert-butyl-1-phenylmethanimine oxide

• ChemBase ID: 81904
• Molecular Formular: C11H15NO
• Molecular Mass: 177.2429
• Monoisotopic Mass: 177.11536411
• SMILES: [N+](=C\c1ccccc1)(/C(C)(C)C)\[O-]
• Canonical SMILES: CC(/[N+](=C/c1ccccc1)/[O-])(C)C
• InChI: InChI=1S/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3
• InChIKey: IYSYLWYGCWTJSG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-tert-butyl-1-phenylmethanimine oxide; (Z)-N-tert-butyl-1-phenylmethenimine oxide; (Z)-tert-butyl(oxido)(phenylmethylidene)azanium
• IUPAC Traditional name: N-tert-butyl-1-phenylmethanimine oxide; (Z)-N-tert-butyl-1-phenylmethenimine oxide; (Z)-tert-butyl(oxido)(phenylmethylidene)azanium
• Synonyms: benzylidene(tert-butyl)ammoniumolate; N-tert-Butyl-α-phenylnitrone; alpha-Phenyl-N-tert-butylnitrone; N-tert-Butyl-alpha-phenylnitrone; N-Benzylidene-tert-butylamine N-oxide; PBN; Phenyl N-t-butylnitrone; N-t-BUTYL-α-PHENYLNITRONE; N-苯亚甲基-叔丁胺-N-氧化物; 苯基·N-叔丁基硝酮; N-叔丁基-α-苯基硝酮

Database IDs

• CAS Number: 3376-24-7
• EC Number: 222-168-6
• MDL Number: MFCD00008799
• Beilstein Number: 2044028
• Merck Index: 147056
• PubChem SID: 162069023; 24850860; 24891981
• PubChem CID: 638877

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.43648198
• LogD (pH = 7.4): -0.117456704
• Log P: -0.44259512
• Molar Refractivity: 56.8585 cm^3
• Polarizability: 20.817497 Å^3
• Polar Surface Area: 26.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 9.367868

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: white powder
• Melting Point: 71-75°C; 73-74 °C(lit.)

Safety Information

• Storage Condition: 2-8°C
• RTECS: TX1760000
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (GC); 98%
• Linear Formula: C6H5CH=N(O)C(CH3)3

DETAILS

Sigma Aldrich - B7263

包装
1, 5 g in glass bottle
Biochem/physiol Actions
N-tert-butyl-α-phenylnitrone (PBN) is a commonly used free-radical spin trap. It has been shown to reduce the number of emboli-induced cerebral microinfarctions in the rabbit cortex and prevent neoplasia by its radical scavenging activity and its ability to inhibit cyclooxygenase-2 activity. Reported to inhibit the induction of nitric oxide synthase (iNOS), thereby preventing the overproduction of nitric oxide (NO). PBN in a dose of 100 mg/kg i.p. reduced necrosis of the substantia nigra, pars reticulate in flurothyl-induced status epilepticus in rats. It protects against some types of post-trauma epileptogenic events in an animal model of epilepsy.1 The lethal dose of PBN in rats was found to be approximately 100 mg/100 g body weight (0.564 mmol/100Å g).

Sigma Aldrich - 180270

Packaging
250 mg in glass bottle
5 g in glass bottle
Application
Useful spin trapping agent.1,2,3
Biochem/physiol Actions
N-tert-butyl-α-phenylnitrone (PBN) is a commonly used free-radical spin trap. It has been shown to reduce the number of emboli-induced cerebral microinfarctions in the rabbit cortex and prevent neoplasia by its radical scavenging activity and its ability to inhibit cyclooxygenase-2 activity. Reported to inhibit the induction of nitric oxide synthase (iNOS), thereby preventing the overproduction of nitric oxide (NO). PBN in a dose of 100 mg/kg i.p. reduced necrosis of the substantia nigra, pars reticulate in flurothyl-induced status epilepticus in rats. It protects against some types of post-trauma epileptogenic events in an animal model of epilepsy.4 The lethal dose of PBN in rats was found to be approximately 100 mg/100 g body weight (0.564 mmol/100Å g).

REFERENCES

• For examples of 1,3-dipolar cycloaddition reactions, see N,ɑ-Diphenyl nitrone, L00185.