4-Chlorobenzotrifluoride

Preparation

4-Chlorobenzotrifluoride is produced commercially by trifluoromethylation of chlorobenzene.

Historically, Occidental Chemical Corporation was a leading producer and sold it as part of its Oxsol product line, specifically under the brand name of Oxsol 100. Occidental Chemical Corporation sold the OXSOL line to Makhteshim Agan Industries, Ltd., in 2002.

Uses

Nitration of PCBTF gives 4-chloro-3,5-dinitrobenzotrifluoride, a precursor to the herbicides trifluralin, fluorodifen, and acifluorfen. It is also a precursor to the insecticide fluvalinate.

PCBTF has also been used as a solvent.

Health and Environmental effects

Health effects:

• Points of entry: eyes, ingestion, inhalation, skin.
• Target organs: central nervous system, kidneys, liver.
• Irritancy: eyes, respiratory tract, skin

In the troposphere, PCBTF has an estimated half-life of 67 days. It is transformed by reaction with photochemically-produced hydroxyl radicals to give mainly 2-chloro-5-trifluoromethylphenol.

Regulation

PCBTF currently has VOC Exempt status from the U.S. Environmental Protection Agency. However, California's Office of Environmental Health Hazard Assessment (OEHHA) has adopted inhalation risk factors for PCBTF as of June 2019, which could have implications for its ongoing VOC Exempt status.

References

References

1. "PCBTF 900, Technical Grade, Liquid, Bulk Datasheet".
2. (2016). "Ullmann's Encyclopedia of Industrial Chemistry".
3. "MSDS provided by Islechem".
4. "Trifluoromethylbenzene 98-08-8". National Cancer Institute.
5. (March 2014). "Para-Chlorobenzotrifluoride (PCBTF) – the 'super-solvent'". The University of Waterloo.
6. (2018-01-30). "EPA Exempt Volatile Organic Compound: Parachlorobenzotrifluoride".
7. "Chemical Listed Effective June 28, 2019 as Known to the State Of California To Cause Cancer: P-Chloro-a,a,a-Trifluorotoluene (Para-Chlorobenzotrifluoride, PCBTF)".
8. [https://oehha.ca.gov/media/downloads/crnr/pcbtfiur012820.pdf p-Chloro-α,α,α-trifluorotoluene (p-Chlorobenzotrifluoride, PCBTF) - Cancer Inhalation Unit Risk Factor Scientific Review Panel Draft - January 2020 - California Office of Environmental Health Hazard Assessment]