Methyl 5-amino-2,4-difluorobenzoate Chemical Properties

Boiling point:

284.0±40.0 °C(Predicted)

Density 

1.355±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.12±0.10(Predicted)

Appearance

Off-white to gray Solid

Safety Information

HS Code 

2922498590

Methyl 5-amino-2,4-difluorobenzoate Usage And Synthesis

Uses

Methyl 5-amino-2,4-difluorobenzoate is a carboxylic acid ester derivative used in pharmaceutical synthesis and experimental research.

Synthesis

General procedure for the synthesis of methyl 5-amino-2,4-difluorobenzoate from methyl 2,4-difluoro-5-nitrobenzoate: to a solution of methyl 2,4-difluoro-5-nitrobenzoate (12.0 g, 0.06 mol, 1 eq.) in acetic acid (150 mL) and water was added iron powder (12.3 g, 0.22 mol, 4 eq.). The reaction mixture was heated to 40 °C and kept for 1.5 hours. After completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford methyl 5-amino-2,4-difluorobenzoate (10.0 g, 96% yield) as a brown solid.1H NMR (400 MHz, DMSO-d6) δppm: 7.27 (dd, J=9.98,7.42 Hz, 1H), 7.14 (t, J=10.99 Hz, 1H), 5.28 (s, 2H), 3.77 (s, 3H).ES-LCMS: m/z 189.0 (M+H).

References

[1] Patent: WO2009/75960, 2009, A1. Location in patent: Page/Page column 22
[2] Patent: WO2009/58919, 2009, A1. Location in patent: Page/Page column 23
[3] Patent: WO2009/58923, 2009, A1. Location in patent: Page/Page column 12
[4] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044

Methyl 5-amino-2,4-difluorobenzoate(125568-73-2)Related Product Information

• 3,4-Difluorobenzoic acid
• 2,4-Difluorobenzoic acid
• Tribenuron methyl
• 1,3-Difluorobenzene
• Methyl acetate
• Pirimiphos-methyl
• Methyl salicylate
• 1,2-Difluorobenzene
• Methyl carbamate
• Methyl anthranilate
• Kresoxim-methyl
• METSULFURON METHYL
• Methyl benzoate
• 5-AMino-4-broMo-2-chloro-benzoic acid Methyl ester
• methyl 5-amino-2-(trifluoromethyl)benzoate
• 5-aMino-2-broMo-4-Methylbenzoic acid Methyl ester
• Thiophanate-methyl
• Methyl-5-amino-2-chlorobenzoate