| Identification | More | [Name]
1-Bromopyrene | [CAS]
1714-29-0 | [Synonyms]
1-BROMOPYRENE
Pyrene, 1-bromo-
2-Bromopyrene
1-Pyrenyl bromide | [EINECS(EC#)]
626-844-5 | [Molecular Formula]
C16H9Br | [MDL Number]
MFCD00015767 | [Molecular Weight]
281.15 | [MOL File]
1714-29-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
102-105 °C (lit.) | [Boiling point ]
255 °C / 7mmHg | [density ]
1.4316 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Soluble), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly) | [form ]
Crystalline | [color ]
White to Pale Yellow | [InChI]
InChI=1S/C16H9Br/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9H | [InChIKey]
HYGLETVERPVXOS-UHFFFAOYSA-N | [SMILES]
C1(Br)=C2C3=C4C(C=C2)=CC=CC4=CC=C3C=C1 | [CAS DataBase Reference]
1714-29-0(CAS DataBase Reference) | [NIST Chemistry Reference]
1-Bromopyrene(1714-29-0) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29039990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow to light brown powder | [Uses]
1-Bromopyrene is used in the cleavage of DNA in studies. It is also used in the preparation of DNA base analogs. | [Preparation]
1-Bromopyrene is an important intermediate in the OLED material industry. The synthesis method is as follows: pyrene is dissolved in an organic solvent dichloromethane, and dibromohydantoin is added for reaction, filtered, and the obtained solid is recrystallized to obtain 1-bromopyrene. | [Synthesis Reference(s)]
Synthetic Communications, 18, p. 2207, 1988 DOI: 10.1080/00397918808082362 | [General Description]
1-Bromopyrene, a polycyclic aromatic hydrocarbon (PAH), is a mono bromo substituted pyrene derivative. Its synthesis has been reported. Its gas phase UV-absorption spectra in the UV wavelength range at elevated temperature has been studied. Electron affinitiy (EA) of 1-bromopyrene has been investigated using electron attachment desorption chemical ionization mass spectrometry (DCI-MS) and triple quadrupole tandem mass spectrometry. It participates in the synthesis of novel ruthenium (II) bipyridine or terpyridine complexes bearing pyrene moiety. The reaction of 1-bromopyrene cation radical with water in acetonitrile has been analyzed using the electron transfer stopped-flow (ETSF) method. | [Synthesis]
The general procedure for the synthesis of 1-bromopyrene from pyrene was as follows: anhydrous N,N-dimethylformamide (DMF, 5 mL) solution of N-bromosuccinimide (NBS, 187 mg, 1.05 mmol) was slowly added dropwise to anhydrous DMF (10 mL) solution of pyrene (252 mg, 1.0 mmol) and the reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the mixture was poured into deionized water (50 mL) and extracted three times with dichloromethane (100 mL). The organic phases were combined, washed thoroughly with deionized water, dried over anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure to remove the solvent to give the crude product 1-bromopyrene (332 mg, 85% yield) as a light yellow solid. The crude product was recrystallized with hexane to obtain pure 1-bromopyrene as light yellow powder, melting point 103-104°C (literature value: 102-104°C). | [References]
[1] Tetrahedron Letters, 2010, vol. 51, # 9, p. 1317 - 1321
[2] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 289 - 296
[3] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4085 - 4088
[4] European Journal of Organic Chemistry, 2011, # 27, p. 5261 - 5271
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2013, vol. 68, # 4, p. 367 - 377 |
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