2,3,6-Trifluorobenzoic acid

Base Information

• Chemical Name: 2,3,6-Trifluorobenzoic acid
• CAS No.: 2358-29-4
• Molecular Formula: C7H3F3O2
• Molecular Weight: 176.095
• Hs Code.: 29163990
• European Community (EC) Number: 624-316-9
• DSSTox Substance ID: DTXSID00334236
• Nikkaji Number: J534.184A
• Wikidata: Q72510859
• Mol file: 2358-29-4.mol

Synonyms:2,3,6-tri-fluorobenzoic acid;2,3,6-trifluorobenzoic acid

Chemical Property of 2,3,6-Trifluorobenzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0308mmHg at 25°C
• Melting Point: 130-131 °C(lit.)
• Boiling Point: 233.5 °C at 760 mmHg
• PKA: 2.00±0.10(Predicted)
• Flash Point: 95 °C
• PSA: 37.30000
• Density: 1.536 g/cm³
• LogP: 1.80210
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 176.00851382
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

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

2,3,6-Trifluorobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1F)C(=O)O)F)F
• Uses: 2,3,6-Trifluorobenzoic acid is a trifluorinated analogue of Benzoic acid (B203900). 2,3,6-Trifluorobenzoic acid is a very useful synthetic intermediate that is commonly used to prepare inhibitors of malaria aspartyl proteases Plasmepsin I and II.

Technology Process of 2,3,6-Trifluorobenzoic acid

There total 9 articles about 2,3,6-Trifluorobenzoic 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: 88.0%

carbon dioxide (124-38-9,18923-20-1) + 1,2,4-trifluorobenzene (367-23-7) → 2,3,6-trifluorobenzoic acid (2358-29-4)

Guidance literature:

carbon dioxide; With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h; under 1125.11 Torr;

1,2,4-trifluorobenzene; In tetrahydrofuran; at 20 ℃; for 12h; under 1125.11 Torr;

With hydrogenchloride; In tetrahydrofuran; water; regioselective reaction;

DOI:10.1021/ja103429q

Reference yield: 88.0%

→ 2,3,6-trifluorobenzoic acid (2358-29-4)

Guidance literature:

With [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(OH)]; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield: 27.0%

(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)hydrazine (1868-85-5) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 2,3,6-trifluorobenzoic acid (2358-29-4)

Guidance literature:

hydrolysis;

DOI:10.1021/jo01033a061

upstream raw materials:

1-bromo-2,4,5-trifluorobenzene

carbon dioxide

(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)hydrazine

2,3,4,6-tetrafluorobenzoic acid

Downstream raw materials:

2,3,6-trifluorobenzyl alcohol

potassium 2,3,6-trifluorobenzoate

Refernces

• 1、 Boogaerts, Ine I. F.,Nolan, Steven P.. "Carboxylation of C-H bonds using N -heterocyclic carbene gold(I) complexes". supporting information; experimental part. p. 8858 - 8859. Retrieved 2010/08/21.
• 2、 Konovalov, Valery V.,Laev, Sergey S.,Beregovaya, Irina V.,Shchegoleva, Lyudmila N.,Shteingarts, Vitalij D.,Tsvetkov, Yuri D.,Bilkis, Itzhak. "Fragmentation of radical anions of polyfluorinated benzoates". . p. 352 - 361. Retrieved 2007/10/03.