1,1,1,3,3,3-Hexachloropropane

There are 29 chlorinated derivatives of propane (four of them being hexachloropropanes, with the formula C₃Cl₆H₂). This was the last one of them to be synthesized—by A. W. Davis and A. M. Whaley—in 1950.^[2]

1,1,1,3,3,3-Hexachloropropane is a liquid that boils at 206 °C.^[1][2] Its boiling point is significantly higher than expected based on estimations from various molecular parameters.^[5][6][7]

The original synthesis by Davis and Whaley obtained the compound by reacting 1,1,3,3-tetrachloropropane and/or 1,1,1,3-tetrachloropropane with chlorine at 80-100 Â°C, through 1,1,1,3,3-pentachloropropane as an intermediate step.^[2]

The compound can be produced quantitatively also by reacting carbon tetrachloride CCl₄ and 1,1-dichloroethene Cl₂C=CH₂ at 80-150 Â°C, with a copper-based catalyst, such as copper(I) chloride or copper(II) chloride, and possibly an amine as co-catalyst.^{[3][8][9][10][11][12][13][14]} The same process can generate higher chlorinated alkanes of the form H₃C−(CH₂−CCl₂)_nCl.^[3][11]

The compound has been considered as an intermediate in the manufacture of 1,1,1,3,3,3-hexafluoropropane, through reaction with hydrogen fluoride.^{[15][16][17][18]}

A 2001 study found that the compound had significant effects on rat fetuses when inhaled at 25 ppm. The LD₅₀ (injection, rats) was found to be 827 mg/kg.^[19][20]

• 1,1,2,2,3,3-Hexachloropropane
• 1,1,1,3,3,3-Hexafluoropropane
• Octachloropropane
• 1,1,1,3,3,3-Hexachloro-2,2-difluoropropane