4-Amino-3,5-difluorobenzoic acid

Base Information

• Chemical Name: 4-Amino-3,5-difluorobenzoic acid
• CAS No.: 500577-99-1
• Molecular Formula: C7H5F2NO2
• Molecular Weight: 173.119
• Hs Code.: 2916399090
• European Community (EC) Number: 867-248-7
• NSC Number: 135302
• DSSTox Substance ID: DTXSID10300184
• Wikidata: Q82043042
• Mol file: 500577-99-1.mol

Synonyms:4-amino-3,5-difluorobenzoic acid;500577-99-1;4-Amino-3,5-difluoro-benzoic acid;Benzoic acid, 4-amino-3,5-difluoro-;MFCD03407440;4-Amino-3,5-difluorobenzoicacid;NSC135302;SCHEMBL1019170;4-ammo-3,5-difluorobenzoic acid;AMY6473;DTXSID10300184;MJHZRTJMDQYAHN-UHFFFAOYSA-N;AKOS012489412;NSC 135302;NSC-135302;SB37364;AC-28627;DS-14756;SY035420;CS-0028247;EN300-98413;10.14272/MJHZRTJMDQYAHN-UHFFFAOYSA-N.1;A856545;doi:10.14272/MJHZRTJMDQYAHN-UHFFFAOYSA-N.1;Z1097087866

Chemical Property of 4-Amino-3,5-difluorobenzoic acid

Chemical Property:

• Boiling Point: 294.2±40.0 °C(Predicted)
• PKA: 4.18±0.10(Predicted)
• PSA: 63.32000
• Density: 1.536±0.06 g/cm3(Predicted)
• LogP: 1.82640
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 173.02883473
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-amino-3,5-difluorobenzoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1F)N)F)C(=O)O
• Uses: 4-Amino-3,5-difluorobenzoic Acid can be used to treat gastric cancer.

Technology Process of 4-Amino-3,5-difluorobenzoic acid

There total 3 articles about 4-Amino-3,5-difluorobenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-amino-3,5-difluorobenzonitrile (110301-23-0) → 4‐amino-3,5-difluorobenzoic acid (500577-99-1)

Guidance literature:

4-amino-3,5-difluorobenzonitrile; With sulfuric acid; In water; at 80 ℃; for 2h;

With sodium hydroxide; In water; at 20 ℃;

DOI:10.1039/c6tc01103a

Reference yield:

4-bromo-2,6-difluoroaniline (67567-26-4) → 4‐amino-3,5-difluorobenzoic acid (500577-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; sodium acetate / water; 1,4-dioxane / 125 °C

2: potassium hydroxide / water / 100 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium acetate; potassium hydroxide; XPhos; In 1,4-dioxane; water;

DOI:10.1021/acs.bioconjchem.7b00665

Reference yield:

2,6-difluoroaniline (5509-65-9) → 4‐amino-3,5-difluorobenzoic acid (500577-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide / acetonitrile / 0 - 21 °C

2: copper(l) iodide / 4 h / 204 °C / Inert atmosphere; Schlenk technique

3: potassium hydroxide / water / 19 h / 110 °C

With N-Bromosuccinimide; copper(l) iodide; potassium hydroxide; In water; acetonitrile;

DOI:10.3390/molecules26133916

upstream raw materials:

4-amino-3,5-difluorobenzonitrile

4-bromo-2,6-difluoroaniline

2,6-difluoroaniline

Downstream raw materials:

3,5-difluoro-4-aminobenzoic acid ethyl ester

Refernces

• 1、 Schultzke, Sven,Staubitz, Anne,Walther, Melanie. "Active ester functionalized azobenzenes as versatile building blocks". supporting information. . Retrieved 2021/07/12.
• 2、 Zhang, Lei,Linden, Greta,Vázquez, Olalla. "In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization". supporting information. p. 2500 - 2508. Retrieved 2019/12/11.