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Names | |
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Preferred IUPAC name 1,1,1,3,3,3-Hexachloropropane | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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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] |
Refractive index (nD) | n20D 1.5179 |
Hazards | |
GHS labelling: | |
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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]
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 °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]
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]
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.
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.
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.
Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also recognised by the IUPAC) is a chemical compound with the chemical formula CCl4. It is a non-flammable, colourless liquid with a "sweet" chloroform-like smell that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.
Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc" (or "PERC"), and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor, similar to the smell of chloroform, detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985.
Trichloroethylene (TCE) is a halocarbon with the formula C2HCl3, commonly used as an industrial degreasing solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell.
Silicon tetrachloride or tetrachlorosilane is the inorganic compound with the formula SiCl4. It is a colorless volatile liquid that fumes in air. It is used to produce high purity silicon and silica for commercial applications. It is a part of the chlorosilane family.
In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.
Hafnium(IV) chloride is the inorganic compound with the formula HfCl4. This colourless solid is the precursor to most hafnium organometallic compounds. It has a variety of highly specialized applications, mainly in materials science and as a catalyst.
Tungsten hexachloride is an inorganic chemical compound of tungsten and chlorine with the chemical formula WCl6. This dark violet blue compound exists as volatile crystals under standard conditions. It is an important starting reagent in the preparation of tungsten compounds. Other examples of charge-neutral hexachlorides are rhenium(VI) chloride and molybdenum(VI) chloride. The highly volatile tungsten hexafluoride is also known.
Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
Thorium(IV) chloride describes a family of inorganic compounds with the formula ThCl4(H2O)n. Both the anhydrous and tetrahydrate (n = 4) forms are known. They are hygroscopic, water-soluble white salts.
Hexachlorobutadiene, (often abbreviated as "HCBD") Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds.
In organosulfur chemistry, a sulfenyl chloride is a functional group with the connectivity R−S−Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS−N and RS−O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.
Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.
Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.
Uranium hexachloride (UCl6) is an inorganic chemical compound of uranium in the +6 oxidation state. UCl6 is a metal halide composed of uranium and chlorine. It is a multi-luminescent dark green crystalline solid with a vapor pressure between 1-3 mmHg at 373.15 K. UCl6 is stable in a vacuum, dry air, nitrogen and helium at room temperature. It is soluble in carbon tetrachloride (CCl4). Compared to the other uranium halides, little is known about UCl6.
Photochlorination is a chlorination reaction that is initiated by light. Usually a C-H bond is converted to a C-Cl bond. Photochlorination is carried out on an industrial scale. The process is exothermic and proceeds as a chain reaction initiated by the homolytic cleavage of molecular chlorine into chlorine radicals by ultraviolet radiation. Many chlorinated solvents are produced in this way.
Octachloropropane or perchloropropane is the chemical compound with elemental formula C3Cl8 and structural formula Cl3C−CCl2−CCl3. Its molecule has a simple chain of three carbon atoms connected by single bonds, with chlorine atoms filling their remaining bonds. It is a chlorocarbon, specifically the third simplest perchloroalkane (after carbon tetrachloride and hexachloroethane. It can be described as a derivative of propane C3H8, with all hydrogen atoms replaced by chlorine.