Hexabromobenzene
Chemical compound
From Wikipedia, the free encyclopedia
Hexabromobenzene (HBB) is an organobromine compound with the formula C6Br6. It features a central benzene ring with six bromine substituents. Hexabromobenzene is a white powder that is not soluble in water but is soluble in ethanol, ether, and benzene. Its bromine content by weight is above 86%.[5]
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| Names | |
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| Preferred IUPAC name
Hexabromobenzene | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.613 |
| EC Number |
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PubChem CID |
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| UNII | |
| UN number | 3077 |
CompTox Dashboard (EPA) |
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| Properties | |
| C6Br6 | |
| Molar mass | 551.490 g·mol−1 |
| Appearance | Monoclinic needles or white powder.[1] |
| Odor | Odorless[2] |
| Melting point | 327 °C (621 °F; 600 K)[2] |
| 0.16 × 10−3 mg/L (insoluble)[1] | |
| Solubility | Slightly soluble in Ethanol, Diethyl ether[3] |
| Solubility in Acetic acid | Soluble[3] |
| Solubility in Benzene | 10%[4] |
| Solubility in Chloroform | 10%[4] |
| Solubility in Petroleum ether | 10%[4] |
| log P | 6.07[1] |
| Hazards | |
| GHS labelling:[2] | |
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| Danger[2] | |
| H302, H312, H315, H319, H332, H335, H413[1] | |
| P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, P501[1] | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | LCSS 6905 |
| Related compounds | |
Related compounds |
Hexafluorobenzene Hexachlorobenzene Hexaiodobenzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Uses
Hexabromobenzene has seen use in high voltage capacitors as a flame retardant.[7]
Hexabromobenzene finds extensive use as a fire retardant additive in a range of materials including plastics, paper, and electrical goods, where it serves as a top-tier flame retardant. It was introduced to replace traditional organobromine fire retardants such as polybrominated derivatives of diphenyl ethers and biphenyls.[8] With a high melting point of 327 °C and a high bromide content of 86.9 wt.%, HBB significantly enhances the fire safety of these materials.[9] Iits widespread application also leads to its dispersion in the environment.
Metabolism
Hexabromobenzene was used in a study investigating its metabolic fate in female rats, wherein the substance was orally administered at doses of 16.6 mg/kg body weight every other day for a span of 2 weeks. Analysis of the rats' excreta revealed the presence of various metabolites, including unchanged HBB, pentabromobenzene, as well as oxygen- and sulfur-containing compounds.[10]
Dangers
Hexabromobenzene poses significant dangers due to its toxicity profile as classified by the GHS (Globally Harmonized System of Classification and Labeling of Chemicals). Classified as GHS07, HBB exhibits acute toxicity via oral, dermal, and inhalation routes, categorizing it under category 4 for this hazard. Additionally, it induces skin and eye irritation, classified under category 2 for both. Moreover, HBB is known to cause skin sensitization (category 1) and specific target organ toxicity upon single exposure (category 3), with the respiratory system being the primary target organ.[11]
The acute toxicity of brominated benzenes decreases with an increase in the number of bromine atoms in the molecule.[12] However, the potential for necrotic changes varies based on the position of these bromine atoms within the molecule. There are severe health risks associated with HBB exposure, warranting careful handling and stringent safety measures in its use and management.[11]