| Identification | Back Directory | [Name]
3-FLUORO-5-FORMYLBENZONITRILE | [CAS]
1003708-42-6 | [Synonyms]
3-FLUORO-5-FORMYLBENZONITRILE
Benzonitrile, 3-fluoro-5-formyl- | [Molecular Formula]
C8H4FNO | [MDL Number]
MFCD04974123 | [MOL File]
1003708-42-6.mol | [Molecular Weight]
149.12 |
| Chemical Properties | Back Directory | [Boiling point ]
205℃ | [density ]
1.25 | [Fp ]
77℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [color ]
Off-white | [InChI]
InChI=1S/C8H4FNO/c9-8-2-6(4-10)1-7(3-8)5-11/h1-3,5H | [InChIKey]
MJDZWYNXMPFSJE-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC(C=O)=CC(F)=C1 |
| Hazard Information | Back Directory | [Uses]
3-Fluoro-5-formylbenzonitrile is benzaldehyde based building block used as a reactant in catalyst-free synthesis of N-β-hydroxyethyl pyrroles and indoles via a domino [3+2] cycloaddition and ring-opening aromatization process. | [Application]
3-FLUORO-5-FORMYLBENZONITRILE can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process. | [Synthesis]
3 -fluoro-5 -formylbenzonitrile : A solution of 3 -bromo-5 -fluorobenzonitrile(5.00 g, 25.0 mmol) in dry THF (25 mL) was cooled to 0 °C and 2M iPrMgCl (15.0 mL, 30.0 mmol) in THF was added dropwise over 5 minutes. The mixture was stirred at 0 °C for 15 minutes then at ambient temperature for 1 hour. The mixture was cooled to 0 °C and dry DMF (5.81 mL, 75.0 mmol) was added. The mixture was stirred for 17 hours during which time the temperature reached ambient temperature after 2 hours. The mixture was added to ice water (150 mL) and Et20 (100 mL). The biphasic mixture was stirred and treated with 6M HC1 to aqueous pH=3. The organic layer was removed and the aqueous layer extracted with Et20 (2X). The combined Et20 fractions were washed with saturated NaCl and dried over MgS04/activated carbon. The dried solution was filtered through a S1O2 plug eluting with Et20. The filtrate was concentrated to give the title compound as a yellow solid that was dried in vacuum (3.68 g, 99percent). 1H NMR (CDC13) δ 10.0 (s, 1H), 8.00 (s, 1H), 7.81-7.86 (m, 1H), 7.62-7.67 (m, 1H). | [References]
[1] Patent: WO2012/158413, 2012, A2. Location in patent: Page/Page column 90
[2] Patent: WO2014/78323, 2014, A1. Location in patent: Paragraph 00542
[3] Patent: WO2014/78372, 2014, A1. Location in patent: Paragraph 00375
[4] Patent: WO2014/78378, 2014, A1. Location in patent: Paragraph 00573 |
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