1,2-dichloroethylene, (cis isomers) appears as a clear colorless liquid with an ether-like odor. Flash point 36-39°F. Denser than water and insoluble in water. Vapors heavier than air. Used in the making of perfumes.
颜色/状态：
Liquid
气味：
Sweetish
蒸汽密度：
3.34 (NTP, 1992) (Relative to Air)
蒸汽压力：
2.00X10+2 mm Hg at 25 °C
亨利常数：
0.01 atm-m3/mole
大气OH速率常数：
2.48e-12 cm3/molecule*sec
稳定性/保质期：
Stable under recommended storage conditions.
自燃温度：
460 °C
分解：
When heated to decomposition it emits toxic fumes of /chloride/.
Cis- and trans-1,1-dichloroethylene bound to the active site of hepatic microsomal cytochrome P-450 with the production of a Type I difference spectrum and stimulated CO-inhibitable hepatic microsomal NADPH oxidation. Incubation of cis- and trans-1,2-dichloroethylene plus hepatic microsomes, NADPH-generating system-EDTA resulted in the production of measurable levels of 2,2-dichloroethanol and dichloroacetaldehyde but not of 2-chloroethanol, chloroacetaldehyde or chloroacetic acid and, also, resulted in decreased levels of hepatic microsomal cytochrome P-450 and heme. In addition, dichloroacetic acid was produced from trans-dichloroethylene under these experimental conditions. The omission of any component of the incubation mixture eliminated the above effects, while the inclusion of SKF-525A, metyrapone or CO:O2 (80, v/v) diminished these effects. The effects of beta-naphthoflavone and phenobarbital pretreatment on the values of Ks, delta Amax, Km and Vmax for the binding and metabolism of the 1,2-dichloroethylenes are reported. The binding and metabolism of the 1,2-dichloroethylenes and the 1,2-dichloroethylene-mediated inactivation of cytochrome P-450 were enhanced per mg of microsomal protein, but generally not per nmole of cytochrome P-450 by prior induction with beta-naphthoflavone or phenobarbital. It is concluded that multiple forms of hepatic microsomal cytochrome P-450 bind and metabolize the 1,2-dichloroethylenes. The role of cytochrome P-450 in the metabolic activation of the dichloroethylenes is considered.
来源:Hazardous Substances Data Bank (HSDB)
代谢
暴露于顺式-1,2-二氯乙烯的老鼠呼出的丙酮速率为每公斤1.95微摩尔/小时。
Rats exposed to cis-1,2-dichloroethylene exhaled acetone at a rate of 1.95 umol/hr/kg.
Similarities and differences have been observed in the metabolism of cis- and trans-1,2-dichloroethene. Both isomers have been shown to bind to the active site of hepatic cytochrome P-450. In addition, classic inhibitors of cytochrome P-450 have been shown to inhibit the production of dichloroacetaldehyde from both isomers. The binding and metabolism of 1,2-dichloroethene do not appear to be specific for any one form of cytochrome P-450. The cis isomer had a 4-fold greater rate of turnover in hepatic microsomes in vitro than the trans isomer. This is consistent with studies on isolated perfused rat livers, where metabolism of the cis isomer occurred at a greater rate than metabolism of the trans isomer. In addition, differences between cis- and trans-1,2-dichloroethene in the rates of formation of dichloroethanol and dichloroacetic acid have been reported in rat hepatocytes.
Animal studies have shown that metabolism of the cis isomer occurs faster than metabolism of the trans isomer, and the cis isomer frequently inhibits activity or destroys cytochrome P-450 levels, while the trans isomer frequently increases the enzyme levels.
IDENTIFICATION AND USE: cis-1,2-Dichloroethylene is a colorless liquid. The cis-isomer of 1,2-dichloroethylene has had only limited use as a solvent and chemical intermediate. It has not developed wide industrial usage in the US partly because of its flammability. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: cis-1,2-Dichloroethylene at 16,000 ppm anesthetized rats in 8 minutes and killed them in 4 hours. The results of repeated exposures of cats and rabbits to vapor concentration of 0.16 to 0.19% in the air was reported. Animals exposed to cis-1,2-dichloroethylene at this concentration showed loss of appetite and some respiratory irritation but no histological changes. cis-1,2-Dichloroethylene was administered daily by gavage to male and female rats at the following dose levels: 1.0, 3.0, 10.0 and 22.0 mmol/kg/day for 14 days. Doses gavaged during the 90-day subchronic study were 0.33, 1.00, 3.00 and 9.00 mmol/kg/day. There were no compound-related deaths or histopathological changes demonstrated. Significant increases in relative liver weights were seen after 14- and 90-days of treatment in both sexes. This study demonstrates some indication of toxicity at subacute and subchronic exposure levels as low as 0.33 mmol/kg/day. Implications of liver abnormalities were demonstrated at an exposure level of 1 mmol/kg/day while kidney abnormalities (relative weights) were demonstrated at an exposure level of 0.33 mmol/kg/day. 1,2-dichloroethylene cis and trans were tested for their ability to induce point mutation, mitotic gene conversion and mitotic recombination in a diploid strain (D7) of the yeast Saccharomyces cerevisiae in a suspension test with and without a mammalian microsomal activation system. In this test both cis and trans isomers were toxic but not genetically active even with metabolic activation. The clastogenic potential of cis-1,2-dichloroethylene was examined using Chinese hamster cells in culture and showed no significant increase in the incidence of chromosome aberrations when used with and without metabolic activation. cis-1,2-Dichloroethylene bound to the active site of hepatic microsomal cytochrome P450 with production of a type-I difference spectrum and stimulated co-inhibitable hepatic microsomal NADPH oxidation.
Under the Guidelines for Carcinogen Risk Assessment (U.S. EPA, 2005a), there is "inadequate information to assess the carcinogenic potential" of cis-1,2-DCE. This cancer descriptor is based on the absence of epidemiological studies in humans and lack of animal studies designed to evaluate the carcinogenic potential of cis-1,2-DCE.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
暴露途径
该物质可以通过吸入其蒸气和摄入的方式被身体吸收。
The substance can be absorbed into the body by inhalation of its vapour and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
毒理性
暴露途径
吸入，吞食，皮肤和/或眼睛接触
inhalation, ingestion, skin and/or eye contact
来源:The National Institute for Occupational Safety and Health (NIOSH)
毒理性
症状
眼睛刺激，呼吸系统；中枢神经系统抑制
irritation eyes, respiratory system; central nervous system depression
来源:The National Institute for Occupational Safety and Health (NIOSH)
In an experiment using isolated perfused liver from female Wistar rats, at equimolar concentrations in the perfusate (with chlorinated ethylenes added as vapors at constant rates that allowed for steady-state conditions of substrate uptake and conversion), uptake for cis-1,2-DCE was about 3 times faster than for trans-1,2-DCE.
/Researchers/ have estimated elimination rate constants for the disappearance from human blood of certain halogenated VOCs, including cis-1,2-DCE. Estimates were based on decay of exhaled breath concentrations following a 10-minute shower exposure to contaminated water and published blood/air partition coefficients for the VOC in question. Two volunteers were exposed in separate showering episodes, in which estimated total absorbed doses of cis-1,2-DCE were 1.19 and 2.34 ug, respectively. The kinetics of elimination of the parent compound from breath suggested the existence of two biological distribution compartments, which were presumed to represent the blood and 'highly perfused tissues' (e.g., liver). In the first fast-elimination compartment (presumed to represent disappearance of cis-1,2-DCE from the blood), elimination half-lives of 0.82 and 2.37 minutes were estimated in the two subjects; corresponding half-lives in the slower, highly perfused tissue compartment were 8.96 and 29.33 minutes, respectively. These limited data suggest the potential for variability in the elimination of cis-1,2-DCE in humans.
Pathways of Chlorinated Ethylene and Chlorinated Acetylene Reaction with Zn(0)
摘要：
To successfully design treatment systems relying on reactions of chlorocarbons with zero-valent metals, information is needed concerning the kinetics and pathways through which transformations occur. In this study, pathways of chlorinated ethylene reaction with Zn(0) have been elucidated through batch experiments. Data for parent compound disappearance and product appearance were fit to pseudo-first-order rate expressions in order to develop a complete kinetic model. Results indicate that reductive beta-elimination plays an important role, accounting for 15% of tetrachloroethylene (PCE), 30% of trichloroethylene (TCE), 85% of cis-dichloroethylene (cis-DCE), and 95% of trans-dichloroethylene (trans-DCE) reaction. The fraction of PCE, TCE, trans-DCE, and cis-DCE transformation that occurs via reductive elimination increases as the two-electron reduction potential (E-2)for this reaction becomes more favorable relative to hydrogenolysis. In the case of PCE a nd TCE, reductive elimination gives rise to chlorinated acetylenes. Chloroacetylene and dichloroacetylene were synthesized and found to react rapidly with zinc, displaying products consistent with both hydrogenolysis and reduction of the triple bond. Surface area-normalized rate constants (k(SA)) for chlorinated ethylene disappearance correlate well with both one-electron (E-1) and two-electron (E-2) reduction potentials for the appropriate reactions. Correlation with E-2 allows prediction of the distribution of reaction products as well as the rate of disappearance of the parent compound.
Reductive Dechlorination of cis-1,2-Dichloroethene and Vinyl Chloride by “Dehalococcoides ethenogenes”
摘要：
cis-Dichloroethene (DCE) and vinyl chloride (VC) often accumulate in contaminated aquifers in which tetrachloroethene (PCE) or trichloroethene (TCE) undergo reductive dechlorination. "Dehalococcoides ethenogenes" strain 195 is the first isolate capable of dechlorinating chloroethenes past cis-DCE. Strain 195 could utilize commercially synthesized cis-DCE as an electron acceptor, but doses greater than 0.2 mmol/L were inhibitory, especially to PCE utilization. To test whether the cis-DCE itself was toxic, or whether the toxicity was due to impurities in the commercial preparation (97% nominal purity), we produced cis-DCE biologically from PCE using a Desulfitobacterium sp. culture. The biogenic cis-DCE was readily utilized at high concentrations by strain 195 indicating that cis-DCE was not intrinsically inhibitory. Analysis of the commercially synthesized cis-DCE by GC/mass spectrometry indicated the presence of approximately 0.4% mol/mol chloroform. Chloroform was found to be inhibitory to chloroethene utilization by strain 195 and at least partially accounts for the inhibitory activity of the synthetic cis-DCE. VC, a human carcinogen that accumulates to a large extent in cultures of strain 195, was not utilized as a growth substrate, and cultures inoculated into medium with VC required a growth substrate, such as PCE, for substantial VC dechlorination. However, high concentrations of PCE or TCE inhibited VC dechlorination. Use of a hexadecane phase to keep the aqueous PCE concentration low in cultures allowed simultaneous utilization of PCE and VC. At contaminated sites in which "D, ethenogenes" or similar organisms are present, biogenic cis-DCE should be readily dechlorinated, chloroform as a co-contaminant may be inhibitory, and concentrations of PCE and TCE, except perhaps those near the source zone, should allow substantial VC dechlorination.
The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.
The synthesis of vicinal bis(dimethylarsino) compounds
作者：Robert D. Feltham、H.Gary Metzger
DOI：10.1016/s0022-328x(00)87418-5
日期：1971.12
bis(dimethylarsino)acetylene, and 1-bromo-1,2-bis(dimethylarisno)ethylene. NaAs(C6H5)2, and NaP(C6H5)2 react with 8-dichloroquinoline to give 8-(diphenylarsino)quinoline and 8-(diphenylphosphino)quinoline, respectively. An improved synthesis of cis-1,2-bis(dimethylarsino)ethylene by hydroboration of bis(dimethylarsino)acetylene is also reported. The proton NMR and mass spectra of these novel arsine compounds
已研究了NaAs（CH 3）2与邻-Cl 2（C 6 H 4）之间的反应，并鉴定出以下产物：（CH 3）2 AsH，o -[（CH 3）2 As] 2 [C 6 H 4 ]，（CH 3）3 As，（CH 3）2 As（C 6 H 5），5,10-二甲基-5,10-二氢ar蒽和甲基双[邻-（二甲基ar基）苯基] ar。NaAs（CH 3）2和CIS -1,2-二氯乙烯给出的混合物中的顺式-和反式-1,2-双（二甲胂基）乙烯，1,2-同时二溴乙烯产量双（二甲胂基）乙炔，和1-溴-1,2- -双（二甲基芳基）乙烯。NaAs（C 6 H 5）2和NaP（C 6 H 5）2与8-二氯喹啉反应，分别得到8-（二苯基di基）喹啉和8-（二苯基膦基）喹啉。还报道了通过双（二甲基ar基）乙炔的氢硼化而改进的顺式-1,2-双（二甲基ar基）乙烯的合成。讨论了这些新颖的砷化氢化合物的质子核磁共振和质谱。
Total Synthesis of Sporolide B and 9-<i>epi</i>-Sporolide B
作者：K. C. Nicolaou、Jianhua Wang、Yefeng Tang、Lorenzo Botta
DOI：10.1021/ja1048994
日期：2010.8.18
The total synthesis of the structurally unique secondary metabolite sporolide B (1b) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system toward a number of indene derivatives as dienophiles, first in intermolecular and thence intramolecular settings. Thus, substrates were devised (37 and
Formal Total Synthesis of Oximidine II via a Suzuki-Type Cross-Coupling Macrocyclization Employing Potassium Organotrifluoroborates
作者：Gary A. Molander、Florian Dehmel
DOI：10.1021/ja047190o
日期：2004.8.1
A formal total synthesis of oximidineII has been achieved, employing a Suzuki-type coupling approach to construct the highly strained, polyunsaturated 12-membered macrolactone. To achieve this goal, benefit was derived from the stability of potassium alkenyltrifluoroborates to establish conditions for the macrocyclization. The stereocontrolled formation of the cis-1,2-diol subunit was accomplished
已经实现了肟 II 的正式全合成，采用 Suzuki 型耦合方法构建了高度应变的多不饱和 12 元大环内酯。为了实现这一目标，从烯基三氟硼酸钾的稳定性中获益，为大环化建立条件。顺式 1,2-二醇亚基的立体控制形成是使用 Carreira 方案使用非对映选择性、试剂控制添加到手性醛中来完成的。利用 Snieckus 硼氢化试剂获得大环化所需的关键三氟硼酸盐。
