To study the metabolic fate of hexabromobenzene (HBB) in female rats, 16.6 mg/kg body wt was given orally every other day for 2 wk and the animals' excreta were examined for metabolites. Unchanged hexabromobenzene pentabromobenzene, O- and S-containing metabolites were detected in feces and urine. The S-containing substances contained free mercapto groups except for the presence in feces of a methylmercapto derivative. The amt of S-containing metabolites was 15-fold greater than that of O-containing cmpd.
The halogenated benzenes, inducers of xenobiotic metabolism, were studied for their effects on the metabolism of malathion, malaoxon (lindane), and paraoxon and on the toxicity and lethality of these organophosphorus insecticides and parathion. One mmol/kg of 1,4-dichlorobenzene (p-dichlorobenzene), 1,2,4-trichlorobenzene, 1,4-dibromobenzene, 1,2,4-tribromobenzene, or hexabromobenzene or 0.1 mmol/kg hexachlorobenzene was administered po to male mice daily for 7 days. In general, the trihalogenated benzenes increased the LD50 of all 4 insecticides 2- to 6-fold. These increases were larger than those observed with the di- or hexahalogenated isomers. The bromide-substituted benzenes were usually more active than the chlorinated ones with the exception being hexabromobenzene. There was a good correlation between their effects on lethality and increases in in vitro carboxylesterase activity with either-malathion or malaoxon as the substrate. The trihalogenated benzenes decreased the inhibitory effect of malathion on cholinesterase activity in the brain and to a lesser degree in the red blood cells, but not in 1iver or plasma.
MALE WISTAR RATS WERE FED A DAILY DIET CONTAINING HEXABROMOBENZENE FOR 12 WK. RESULTS INDICATED THAT IN GENERAL NO DIFFERENCE IN HEMATOLOGIC PARAMETERS & BODY ORGAN WEIGHTS WERE OBSERVED BETWEEN TREATED & CONTROL RATS. HOWEVER, SERUM CARBOXYLESTERASE ACTIVITY TOWARD INDOPHENYL ACETATE WAS INDUCED @ 60, 80, & 160 PPM OF HEXABROMOBENZENE.
MALE SPRAGUE-DAWLEY RATS WERE GIVEN 400 MG/KG OF HEXABROMOBENZENE DAILY IN CORN OIL FOR 14 DAYS. CYTOCHROME C REDUCTASE ACTIVITY INCREASED. /BUT THE INCREASE IN SPECIFIC CONTENT OF CYTOCHROME P450 (1.09 + OR - 0.18 TO 1.33 + OR -0.08 MM/MG) WAS NOT STATISTICALLY SIGNIFICANT./ THE WAVELENGTH MAXIMUM FOR CYTOCHROME P450 PEAK WAS 449.4 NM.
Hexabromobenzene (HBB) was admin to pregnant CD-1 mice from day 6-16 of gestation by gastric intubation. Hexabromobenzene was not teratogenic or fetotoxic at doses up to 98.6 mg/kg. No maternal toxicity was noted.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
非人类毒性摘录
六溴苯未显著诱导肝脏卟啉症，也未导致卟啉分泌增加。
Hexabromobenzene did not induce hepatic porphyria to any significant degree and did not cause increases in secretion of porphyrins.
Pregnant Wistar rats were given hexabromobenzene (>99% pure) at 25-200 mg/kg by oral intubation on days 6-15 of gestation. The rats were killed on day 22. The concn of hexabromobenzene was highest in the fat. The compound was present in the maternal liver, brain, heart, kidney, and spleen, as well as in fetal tissue. ... Reported that fat was the only tissue in which the concentration showed a dose response relationship.
A study of the occurrence of hexabromobenzene and its debrominated compounds in human adipose tissue was conducted. Human adipose tissues were obtained from Shikoku Center Hospital, Matsuyama, Japan. The extracts were analyzed by gas chromatography/mass spectrometry. Hexabromobenzene, pentabromobenzene, and 1,2,4,5-tetrabromobenzene were detected at concentrations of 2.1 to 4.1 ng/g. 1,2,4,5-Tetrabromobenzene was found in largest amount, followed by hexabromobenzene and pentabromobenzene in that order. The samples also contained 350 to 1400 ng/g polychlorinated-biphenyls, 1100 to 1800 ng/g total DDT, and 20 to 92 ng/g hexachlorobenzene. Pentabromobenzene and 1,2,4,5-tetrabromobenzene found in human adipose tissue may be metabolism products of hexabromobenzene.
Movement of brominated benzenes in rat and mice was investigated. The concentration of hexabromobenzene following continuous ip administration reached the highest value 16.3 (liver) to 28.8 days (brain) after administration. The biological half life of hexabromobenzene ranged from 2.0 (kidney) to 4.1 days (brain) in the 1st phase of excretion, and from 5.2 (kidney) to 7.3 days (adipose tissue) in the 2nd phase of excretion.
The distribution and excretion of hexabromobenzene and hexachlorobenzene were studied in male Wistar-rats fed 0.2 mg of hexabromobenzene or hexachlorobenzene orally in 1 ml of corn oil. On the first day, 10% of the hexabromobenzene dose and 5% of the hexachlorobenzene dose was detected in the feces; very minimal excretion of hexabromobenzene in feces was found subsequently. By day four, cumulative excretion of hexabromobenzene and hexachlorobenzene plateaued at about 10% of the given dose, indicating a similar course of intestinal absorption for both chemicals. Urinary excretion did not appear to be a significant route of excretion for either compound. Concentrations of hexabromobenzene and hexachlorobenzene in blood were nearly the same during the first 8 hours but diverged after day one and indicated a faster metabolism of hexabromobenzene. Rapid metabolism of hexabromobenzene was also shown by the concentration curve in liver; the highest liver concentrations were found within 1 hour of administration. Maximum hexachlorobenzene concentrations appeared 4 to 24 hours after administration. The hexabromobenzene concentration curve in the kidney was similar to that of the liver, thus hexabromobenzene might be carried from the liver to kidney directly, indicating that kidney has no, or very little, metabolic capacity for hexabromobenzene. In adipose tissue, the course patterns of concentration of hexabromobenzene and hexachlorobenzene were similar but the concentration of hexachlorobenzene was much higher. The elimination of hexabromobenzene from the rat body was clearly biphasic, while that of hexachlorobenzene was not. The half lives for hexachlorobenzene were 0.7 for phase-I and 48 days for phase-II and the half life for hexachlorobenzene was 20 days.
(η6-[7]Heliphene)tricarbonylchromium via an Optimized Preparation of [7]Heliphene
摘要：
Optimized procedures to [7]heliphene are described that allowed the synthesis of ((6)-[7]heliphene)tricarbonylchromium and a preliminary exploration of its chemical behavior. DFT calculations provide structural and energetic information on this complex and its haptomeric isomers. Attempts to prepare the corresponding ([7]heliphene)chromium sandwich failed so far, but DFT evidence is presented to indicate that the target should be accessible.
Six- and Eightfold Palladium-Catalyzed Cross-Coupling Reactions of Hexa- and Octabromoarenes
作者：Baldur Stulgies、Peter Prinz、Jörg Magull、Karsten Rauch、Kathrin Meindl、Stephan Rühl、Armin de Meijere
DOI：10.1002/chem.200400723
日期：2005.1
Palladium-catalyzedsixfold coupling of hexabromobenzene (20) with a variety of alkenylboronates and alkenylstannanes provided hexaalkenylbenzenes 1 in up to 73 % and 16 to 41 % yields, respectively. In some cases pentaalkenylbenzenes 21 were isolated as the main products (up to 75 %). Some functionally substituted hexaalkenylbenzene derivatives containing oxygen or sulfur atoms in each of their six
Aqueous Ammonia as a New Activator for Sonogashira Coupling
作者：Mohamed S. Mohamed Ahmed、Akitoshi Sekiguchi、Kentaro Masui、Atsunori Mori
DOI：10.1246/bcsj.78.160
日期：2005.1
Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.
ASYMMETRIC ORGANIC PEROXIDE, CROSSLINKING AGENT COMPRISING THE SAME, AND METHOD OF CROSSLINKING WITH THE SAME
申请人：NOF CORPORATION
公开号：EP1233014A1
公开（公告）日：2002-08-21
A crosslinking agent comprising an asymmetry organic peroxide having at least one structure unit of (substituted)benzoylcarbonyloxy group represented by the following formula (1) in the molecule thereof.
Environmentally friendly crosslinking agents and crosslinked silicone rubber moldings are provided thereby.
Specifically, useful crosslinking agents and crosslinking processes for silicone rubber are provided.
How Do Redox Groups Behave around a Rigid Molecular Platform? Hexa(ferrocenylethynyl)benzenes and Their “Electrostatic” Redox Chemistry
作者：Abdou K. Diallo、Jean-Claude Daran、François Varret、Jaime Ruiz、Didier Astruc
DOI：10.1002/anie.200900216
日期：2009.4.14
A new family of hexakis(ferrocenylethynyl)benzenes was synthesized by Negishi coupling from ethynylferrocenes and C6Br6 and can be reversibly oxidized to stable hexaferrocenium salts (see picture, ArF=[3,5‐C6H3(CF3)2]). Their cyclic voltammograms show a single six‐electron wave, three distinct two‐electron waves, or a cascade of six single‐electron waves, depending on the electrolyte counterion and
Negishi偶联通过乙炔基二茂铁和C 6 Br 6合成了一个新的六（二茂铁基乙炔基）苯族，并且可以可逆地氧化成稳定的六茂铁鎓盐（参见图片，Ar F = [3,5-C 6 H 3（CF 3））2 ]）。它们的循环伏安图显示单个六电子波，三个截然不同的两个电子波或六个六个单电子波的级联，具体取决于电解质的抗衡离子和二茂铁基上的甲基取代基数量。
Highly Conductive 2D Metal–Organic Framework Thin Film Fabricated by Liquid–Liquid Interfacial Reaction Using One-Pot-Synthesized Benzenehexathiol
作者：Iu-Fan Chen、Chun-Fu Lu、Wei-Fang Su
DOI：10.1021/acs.langmuir.8b03938
日期：2018.12.26
Metal–organicframeworks (MOF) are studied extensively in applications like catalysts, gas storage, and sensors due to their various functional groups and structures. Two-dimensional (2D) MOFs such as triphenylene-based materials show excellent charge transport properties, but thin-film fabrication and organic ligand synthesis are difficult. In this work, we synthesize thiol-based organic ligand, benzenehexathiol
金属有机骨架（MOF）由于其各种官能团和结构而在催化剂，气体存储和传感器等应用中得到了广泛的研究。二维（2D）MOF（例如基于三亚苯基的材料）显示出出色的电荷传输性能，但薄膜制造和有机配体合成很困难。在这项工作中，我们通过一个简单的一锅反应合成了基于硫醇的有机配体苯六硫醇（BHT）。这种简便的方法比需要使用液氨作为溶剂的常规合成过程更安全，更快捷。两种新颖的2D MOF材料Ag 3 BHT 2和Au 3 BHT 2，是通过液-液界面反应将BHT与银（Ag）或金（Au）离子配位而制成的。Ag 3 BHT 2薄膜具有363 S cm –1的高电导率，在电子设备和传感器中具有潜在的应用。
