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4-Amino-2-fluoro-5-methoxybenzoic acid

4-Amino-2-fluoro-5-methoxybenzoic acid structure

4-Amino-2-fluoro-5-methoxybenzoic acid 

structure
  • CAS No:

    1001346-91-3

  • Formula:

    C8H8FNO3

  • Chemical Name:

    4-Amino-2-fluoro-5-methoxybenzoic acid

  • Synonyms:

    4-Amino-2-fluoro-5-methoxybenzoic acid;4-amino-6-fluoro-3-methoxy-benzoic acid;Benzoic acid, 4-amino-2-fluoro-5-methoxy-;SCHEMBL1163576;CTK6J5247;KS-00000HTN;DTXSID00680700;ANW-61657;ZINC63772434;AKOS016002906

  • Categories:

    Chemical Reagents  >  Organic Reagents

4-Amino-2-fluoro-5-methoxybenzoic acid Basic Attributes

185.1524232

185.048828

DTXSID00680700

Characteristics

72.6

0.8

1.4±0.1 g/cm3

176.9±27.9 °C

1.580

Safety Information

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

H302

4-Amino-2-fluoro-5-methoxybenzoic acid Use and Manufacturing

4-Amino-2-fluoro-5-methoxybenzoic acid: A solution of 2-fluoro-5-methoxy- 4-nitrobenzoic acid (10 g, 46 mmol), HOAc (50 mL) and MeOH (50 mL) was hydrogenated using a hydrogen balloon overnight. The solution was then filtered through celite and concentrated to a residue, which was triturated with ether and ethyl acetate. The solid was filtered and dried to give the product as light yellow powder (8.3 g, 98percent). 2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 12; 7.76 g, 36.1 mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770 mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent)2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 28; 7.76g, 36.1mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent) 2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 28; 7.76g, 36.1mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent)

Computed Properties

Molecular Weight:185.15
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:185.04882128
Monoisotopic Mass:185.04882128
Topological Polar Surface Area:72.6
Heavy Atom Count:13
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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