Chemical Properties
yellow-green powder
Uses
1-Aminopyrene is used in the synthesis of novel fluorescent nanoscale ionic silicate platelets for use in bacterial detection and other biosensor applications.
Uses
It acts as a precursor molecule for production of other fluorescent probes such as 1-Azidopyrene, APTS, and N-(1-Pyrene)iodoacetamide.
General Description
Colorless crystals. Yellow needles from hexane, melting point 117-8°C.
Reactivity Profile
1-Aminopyrene neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.
Fire Hazard
1-Aminopyrene is probably combustible.
Synthesis
Under argon protection and magnetic stirring conditions, 1-nitropyrene (1.00 g, 4.0 mmol) was dissolved in 60 mL of ethyl acetate with tin(II) chloride dihydrate (4.35 g, 19.2 mmol) in a 250 mL three-necked round-bottomed flask. The reaction mixture was heated to reflux for 6 hours. After the reaction was completed, it was cooled to room temperature and the pH was adjusted to 8.0 by slowly adding 20% (m/v) aqueous sodium carbonate solution and continued stirring for 1 hour. The reaction mixture was extracted three times with ethyl acetate, the organic phases were combined and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give a light green solid product 1-aminopyrene 0.80 g (90% yield). The product was characterized by the following data: melting point 115-116 °C (literature value: 115-117 °C); IR (KBr) νmax/cm1: 3345-3387 (N-H stretching vibration), 3036 (aromatic C-H stretching vibration), 1623-1512 (C=C stretching vibration); 1H NMR (400 MHz, DMSO-d) δ: 8.24 (d, 1H, J=9.4 Hz, Ar-H), 7.97 (d, 2H, J=7.8 Hz, Ar-H), 7.94 (d, 1H, J=7.8 Hz, Ar-H), 7.89 (d, 1H, J=9.0 Hz, Ar-H), 7.86 (d, 1H, J=8.6 Hz, Ar-H), 7.85 (t, 1H, J=7.6 Hz, Ar-H), 7.69 (d, 1H, J=8.6 Hz, Ar-H), 7.34 (d, 1H, J=8.2 Hz, Ar-H), 6.33 (s, 2H, NH).
Purification Methods
1-Aminopyrene [1606-67-3] M 217.3, m 117-118o, pK 1 2.91 (50% aqueous EtOH), pK 2 2.77 (50% aqueous EtOH). Crystallise it from hexane. [Beilstein 12 IV 3460.]
References
[1] Analytical Chemistry, 1988, vol. 60, # 3, p. 194 - 199
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7663 - 7673
[3] Tetrahedron Letters, 1998, vol. 39, # 40, p. 7243 - 7246
[4] Synthetic Communications, 1991, vol. 21, # 2, p. 161 - 165
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 593 - 605
