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

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1,1,1,3,3,3-Hexachloropropane
1,1,1,3,3,3-Hexachloropropane.svg
1,1,1,3,3,3-Hexachloropropane 3D volume.png
Names
Preferred IUPAC name
1,1,1,3,3,3-Hexachloropropane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C3H2Cl6/c4-2(5,6)1-3(7,8)9/h1H2
    Key: BBEAZDGZMVABIC-UHFFFAOYSA-N
  • C(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
Properties
C3H2Cl6
Molar mass 250.77 g/mol
Density d204 1.68 g/mL
Melting point −27 °C [1] [2]
Boiling point 206 °C (760 torr), [1] [2] 114-124 °C (20 torr), [3] 89 °C (16 torr) [1] [2]
n20D 1.5179
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H315, H319, H332, H335, H400
P261, P264, P271, P273, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,1,1,3,3,3-Hexachloropropane is a compound of chlorine, hydrogen, and carbon, with chemical formula C3Cl6H2, specifically Cl3C−CH2−CCl3. Its molecule can be described as that of propane with chlorine atoms substituted for the six hydrogen atoms on the extremal carbons. [4]

Contents

History and properties

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]

Production

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 °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 °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]

Applications

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]

Safety

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]

See also

Related Research Articles

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<span class="mw-page-title-main">Chlorofluorocarbon</span> Class of organic compounds commonly used as refrigerants

Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propane.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Carbon tetrachloride</span> Chemical compound

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<span class="mw-page-title-main">Trichloroethylene</span> Chemical compound

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<span class="mw-page-title-main">Silicon tetrachloride</span> Chemical compound

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<span class="mw-page-title-main">Sulfenyl chloride</span> Chemical group (R–S–Cl)

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References

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