5-Fluoro-1,3-benzodioxole-4-carboxylic acid

Base Information

• Chemical Name: 5-Fluoro-1,3-benzodioxole-4-carboxylic acid
• CAS No.: 492444-08-3
• Molecular Formula: C₈H₅FO₄
• Molecular Weight: 184.124
• European Community (EC) Number: 826-443-7
• DSSTox Substance ID: DTXSID40591907
• Wikidata: Q82485773
• Mol file: 492444-08-3.mol

Synonyms:492444-08-3;5-FLUORO-1,3-BENZODIOXOLE-4-CARBOXYLIC ACID;5-fluorobenzo[d][1,3]dioxole-4-carboxylic acid;5-fluoro-2H-1,3-benzodioxole-4-carboxylic acid;SCHEMBL4493633;DTXSID40591907;AKOS006330588;5-fluoro-1,3-dioxaindane-4-carboxylic acid;5-fluorobenzo[d][1,3]dioxole-4-carboxylicacid;EN300-174927;Z1198184431

Chemical Property of 5-Fluoro-1,3-benzodioxole-4-carboxylic acid

Chemical Property:

• PSA: 55.76000
• LogP: 1.25260
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 184.01718680
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

5-FLUORO-1,3-BENZODIOXOLE-4-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C(=C(C=C2)F)C(=O)O

Technology Process of 5-Fluoro-1,3-benzodioxole-4-carboxylic acid

There total 7 articles about 5-Fluoro-1,3-benzodioxole-4-carboxylic 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: 97.0%

methyl 5-fluoro-1,3-benzodioxole-4-carboxylate (492444-07-2) → 5-fluoro-1,3-benzodioxole-4-carboxylic acid (492444-08-3)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 3h;

DOI:10.1021/jm030317k

Reference yield:

carbon monoxide (201230-82-2) + 5-fluorobenzo[d][1,3]dioxolene (147900-49-0) → 5-fluoro-1,3-benzodioxole-4-carboxylic acid (492444-08-3)

Guidance literature:

5-fluorobenzo[d][1,3]dioxolene; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

carbon monoxide; In tetrahydrofuran; at 20 ℃;

Reference yield:

4-fluoroveratrole (398-62-9) → 5-fluoro-1,3-benzodioxole-4-carboxylic acid (492444-08-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -60 °C

1.2: 64 percent / tetrahydrofuran; hexane / 0.5 h / -60 °C

2.1: 100 percent / HBr; AcOH / H₂O / 1 h / Heating

3.1: 60 percent / SOCl₂ / 18 h / 70 °C

4.1: 80 percent / Cs₂CO₃ / dimethylformamide / 1.5 h / 110 °C

5.1: 97 percent / KOH / methanol; H₂O / 3 h / 20 °C

With potassium hydroxide; thionyl chloride; hydrogen bromide; caesium carbonate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm030317k

upstream raw materials:

methyl 5-fluoro-1,3-benzodioxole-4-carboxylate

4-fluoroveratrole

6-fluoro-2,3-dimethoxybenzoic acid

6-fluoro-2,3-dihydroxybenzoic acid

Downstream raw materials:

tert-butyl (5-fluoro-1,3-benzodioxol-4-yl)carbamate

5-fluoro-1,3-benzodioxol-4-amine