| Identification | Back Directory | [Name]
6-BROMONAPHTHALEN-2-AMINE | [CAS]
7499-66-3 | [Synonyms]
7499-66-3
F0701-0046
NSC 407685
2-Amino-6-bromophthalene
6-BroMo-2-naphthalenaMine
6-Bromonaphthalen-2-amine
6-broMo-2-aMinonaphthalene
2-Amino-6-bromonaphthalene
6-Bromonaphthalen-2-ylamine
2-Naphthalenamine, 6-bromo-
6-Bromo-2-naphthylamine, 6-Bromonaphthalen-2-amine | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C10H8BrN | [MDL Number]
MFCD01026466 | [MOL File]
7499-66-3.mol | [Molecular Weight]
222.08 |
| Chemical Properties | Back Directory | [Melting point ]
128 °C | [Boiling point ]
155-160 °C(Press: 1 Torr) | [density ]
1.563±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
solid | [pka]
3.66±0.10(Predicted) | [color ]
grey | [InChI]
InChI=1S/C10H8BrN/c11-9-3-1-8-6-10(12)4-2-7(8)5-9/h1-6H,12H2 | [InChIKey]
UBLKHAWYJFEPDX-UHFFFAOYSA-N | [SMILES]
C1=C2C(C=C(Br)C=C2)=CC=C1N |
| Hazard Information | Back Directory | [Uses]
6-Bromonaphthalen-2-amine(7499-66-3) is used in the new synthesis of alkylsulphanylnaphthalenes and the synthesis and mesomorphic properties of novel naphthylisothiocyanates.
| [Application]
6-Bromonaphthalen-2-amine(7499-66-3) can be used to prepare light-emitting diode materials, amine compounds, deuterated aromatic compounds and deuterated compositions thereof.
| [Synthesis]
6-Bromo-2-naphthoic acid (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) were treated with the diphenylphosphoroyl azide (6.55mL, 8.34g, 30.3mmol) followed by stirring at room temperature for 3h. The solution was then treated with water (2OmL) and warming at 1000C for Ih. The solution was cooled in the flask fitted with a short-path distillation head, and the DMF was removed by distillation under a high vacuum. The solid residue was dissolved in EtOAc and washed with a saturated sodium bicarbonate solution. Filtered through celite, the filtrate was washed with water (3x) and brine. Dried over, filtered, and concentrated under vacuum to give 6-Bromonaphthalen-2-amine as a beige solid (4.48g, 100 percent).
| [References]
[1] Patent: WO2009/39127, 2009, A1. Location in patent: Page/Page column 175
[2] Patent: WO2009/39134, 2009, A1. Location in patent: Page/Page column 104
[3] Patent: WO2010/111437, 2010, A1. Location in patent: Page/Page column 74
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3793 - 3799
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 12, p. 1651 - 1655 |
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