3-Chloro-2,4,5-Trifluorobenzoic Acid

3-Chloro-2,4,5-Trifluorobenzoic Acid C₇H₂ClF₃O₂

CAS NO.101513-77-3

3-Chloro-2,4,5-Trifluorobenzoic Acid: A Versatile Building Block in Organic Synthesis

 

 

3-Chloro-2,4,5-trifluorobenzoic acid (CTFBA) is a colorless to white crystalline solid that is widely used in organic synthesis as a versatile building block for the preparation of various biologically active compounds, such as pharmaceuticals and agrochemicals. This article will discuss the properties, synthesis, and applications of CTFBA.

 

Properties of CTFBA:

CTFBA contains a chloro and three fluoro substituents on a benzoic acid ring, which impart unique properties to the molecule. It has a molecular weight of 242.51 g/mol and a melting point of 128-131°C. CTFBA is sparingly soluble in water, but soluble in most organic solvents. It is an acidic compound with a pKa value of 3.9.

 

Synthesis of CTFBA:

CTFBA is commonly synthesized from 2,4,5-trifluorobenzoic acid, which is reacted with thionyl chloride to form the corresponding acid chloride. The acid chloride is then treated with either chlorosulfonic acid or hydrogen chloride gas to introduce the chlorine substituent, resulting in the formation of CTFBA. The synthesis of CTFBA can also be achieved via other routes, such as direct chlorination of 2,4,5-trifluorobenzoic acid using N-chlorosuccinimide (NCS) or sodium hypochlorite.

 

Applications of CTFBA:

CTFBA is a highly versatile building block for the preparation of various biologically active compounds. It has been extensively used in the synthesis of pharmaceuticals, such as antiviral agents, anticancer drugs, and analgesics. For example, CTFBA has been employed as a key starting material for the preparation of remdesivir, a drug that has been approved by the FDA for the treatment of COVID-19. Additionally, CTFBA is important in the synthesis of agrochemicals, such as herbicides, fungicides, and insecticides. For instance, CTFBA has been used in the preparation of pyrazole fungicides that are effective against plant diseases.

Apart from its use in organic synthesis, CTFBA has other applications as well. It has been employed as an analytical reagent for flame atomic absorption spectrometry, which is used to determine the content of various metals in environmental samples. CTFBA has also been utilized as a corrosion inhibitor for mild steel in acidic media.

 

 

 

 

[Density]: 1.7±0.1 g/cm³

[Boiling point]: 272.0±35.0 ℃ at 760 mmHg

[Melting point]: 112-116 ℃ (lit.)

[Molecular formula]: C7H₂ClF₃O₂

[Molecular weight]: 210.538

[Flash point]: 118.3±25.9 ℃

[Exact Mass]: 209.969543

[PSA]: 37.30000

[LogP]: 3.10

[Appearance]: white powder

[Vapor pressure]: 0.0±0.6 mmHg at 25℃

[Refractive Index]: 1.513

[ Storage conditions ]:

Store airtight in a cool, dry warehouse. Keep away from oxidizing agents.

[Stability]:

Stable under normal temperature and pressure, avoid contact with strong oxidants.

 

[ Molecular Structure ]:

1. Molar refractive index: 38.05

2. Molar volume (cm³/mol): 126.5

3. Isotonic specific volume (90.2K): 326.6

4. Surface tension (dyne/cm): 44.3

5. Dielectric constant: None available

6. Polarizability (10⁻²⁴cm³): 15.08

7. Single isotope mass: 209.969542 Da

8. Nominal mass: 210 Da

9. Average mass: 210.5378 Da

Packing, Storage, Handling and Transportation

3-Chloro-2,4,5-trifluorobenzoic Acid should be kept in dark place and sealed in dry place at room temperature.

 

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