TCPy

TCPy or 3,5,6-trichloro-2-pyridinol is a cyclic hydrocarbon, specifically a chlorinated version of 2-pyridone.

TCPy
Names
Preferred IUPAC name
3,5,6-Trichloropyridin-2(1H)-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.733
UNII
  • InChI=1S/C5H2Cl3NO/c6-2-1-3(7)5(10)9-4(2)8/h1H,(H,9,10) checkY
    Key: WCYYAQFQZQEUEN-UHFFFAOYSA-N checkY
  • InChI=1/C5H2Cl3NO/c6-2-1-3(7)5(10)9-4(2)8/h1H,(H,9,10)
    Key: WCYYAQFQZQEUEN-UHFFFAOYAM
  • O=C1C(Cl)=CC(Cl)=C(Cl)N1
Properties
C5H2Cl3NO
Molar mass 198.43 g·mol−1
Density 1.67g/cm3
Melting point 172 to 174 °C (342 to 345 °F; 445 to 447 K)
Boiling point 254.8 °C (490.6 °F; 528.0 K) at 760 mmHg
Hazards
Flash point 107.9 °C (226.2 °F; 381.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Pesticides can be a precursor to TCPy. TCPy is a metabolite of the herbicide triclopyr,[1] and of the insecticides chlorpyrifos and chlorpyrifos-methyl. A study in Massachusetts reported a correlation between exposure to TCPy and lower testosterone levels in men.[2] According to this source, exposure is "widespread" and of "potential public health importance".

References
  1. "Draft Vegetation Management: Triclopyr" (PDF). San Francisco Forest Alliance. Marin Municipal Water District. 2008. Retrieved 12 April 2021.
  2. Meeker, J. D.; Ryan, L.; Barr, D. B.; Hauser, R. (2006). "Exposure to Nonpersistent Insecticides and Male Reproductive Hormones". Epidemiology. 17 (1): 61–68. doi:10.1097/01.ede.0000190602.14691.70. PMID 16357596.
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