ChemicalBook CAS DataBase List 3,4-Diaminofluorobenzene

3,4-Diaminofluorobenzene synthesis

9synthesis methods

Product Name:3,4-Diaminofluorobenzene
CAS Number:367-31-7
Molecular formula:C6H7FN2
Molecular Weight:126.13

2369-11-1

367-31-7

General procedure for the synthesis of 4-fluoro-1,2-benzenediamine from 5-fluoro-2-nitroaniline: a methanol solution of 5-fluoro-2-nitroaniline (0.32 M) was added to a palladium/carbon catalyst (5% w/w, 10% w). The reaction mixture was stirred for 2 h at room temperature under hydrogen atmosphere (50 psi). Upon completion of the reaction, the mixture was filtered to remove the catalyst and the filtrate was concentrated to afford 4-fluoro-1,2-benzenediamine in 90% yield as a brown oil. Mass spectrometry (electrospray positive ion mode) analysis: the theoretical molecular weight of C6H7FN2 was 126 and the measured value was 127 (M + H)+.

2369-11-1 Synthesis

2369-11-1
227 suppliers
$6.00/5g

367-31-7
225 suppliers
$8.00/1g

Yield:367-31-7 95%

Reaction Conditions:

with ethanol;stannous chloride at 80; for 4 h;Inert atmosphere;

Steps:

2.3.1 Preparation of 5-Fluoro-1,2-diaminobenzene (1)

To a 50 mL round bottom flask was added 2-nitro-5-fluoroaniline (1.56 g, 10 mmol) and ethanol 20 mL. Anhydrous SnCl2 (9.47 g, 50 mmol, 5 equiv.) as a solid. The flask was equipped with a condenser and placed in an 80 °C sand bath under N2 and the mixture was refluxed for 4 h. The reaction was poured into a sep. funnel, diluted with 80 mL dichloromethane and then treated with 100 mL 2M NaOH. The resulting emulsion was filtered through Celite to remove all the tin, and the resulting biphasic mixture was separated in a sep. funnel. The aq. phase was washed with dichloromethane (50 mL) and the combined organic phases were dried with brine (30 mL), dried over MgSO4, filtered and concentrated to afford a yellow solid.1.21 g, 95%.¹H NMR (300 MHz, Chloroform-d) δ 6.64 (dd, J = 8.4, 5.5 Hz, 1H), 6.46 (dd, J = 9.9, 2.8 Hz, 1H), 6.39 (td, J = 8.5, 2.8 Hz, 1H), 3.35 (s, 4H). Spectral data are in agreement with the literature. Chen et al., 2018.

References:

WO2022/61140,2022,A1 Location in patent:Page/Page column 79-80

364-78-3 Synthesis