(3R)-1-(7-nitro-2,1,3-benzoxadiazol-4-yl)pyrrolidin-3-amine

• ChemBase ID: 156566
• Molecular Formular: C10H11N5O3
• Molecular Mass: 249.22604
• Monoisotopic Mass: 249.08618924
• SMILES: c1cc(c2c(c1N1CC[C@H](C1)N)non2)[N+](=O)[O-]
• Canonical SMILES: N[C@@H]1CCN(C1)c1ccc(c2c1non2)[N+](=O)[O-]
• InChI: InChI=1S/C10H11N5O3/c11-6-3-4-14(5-6)7-1-2-8(15(16)17)10-9(7)12-18-13-10/h1-2,6H,3-5,11H2/t6-/m1/s1
• InChIKey: QSDDQXROWUJAJX-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-1-(7-nitro-2,1,3-benzoxadiazol-4-yl)pyrrolidin-3-amine
• IUPAC Traditional name: (3R)-1-(7-nitro-2,1,3-benzoxadiazol-4-yl)pyrrolidin-3-amine
• Synonyms: (R)-(-)-1-(7-Nitro-4-benzofurazanyl)-3-pyrrolidinamine; (R)-(-)-NBD-APy; (R)-(-)-4-(3-Aminopyrrolidino)-7-nitrobenzofurazan

Database IDs

• CAS Number: 143112-51-0
• MDL Number: MFCD00191510
• PubChem SID: 24889649; 162250703
• PubChem CID: 15682840

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -2.489227
• LogD (pH = 7.4): -1.8122627
• Log P: 0.5225146
• Molar Refractivity: 64.4045 cm^3
• Polarizability: 24.208258 Å^3
• Polar Surface Area: 114.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~190 °C (dec.)
• Fluorescence: λex 490 nm; λem 535 nm in acetonitrile

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: for fluorescence; purum p.a.
• Empirical Formula (Hill Notation): C10H11N5O3

DETAILS

Sigma Aldrich - 92955

Other Notes
Reagent for the fluorescent chiral derivatization of carboxylic acids prior to HPLC1; peroxyoxalate chemiluminescence detection2