O-terphenyl appears as colorless or light-yellow solid. mp: 58-59° C, bp: 337°C. Density: 1.16 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers m-terphenyl and p-terphenyl that is used as a heat-transfer fluid.
颜色/状态:
MONOCLINIC PRISMS FROM METHANOL
蒸汽密度:
7.95 (AIR= 1)
蒸汽压力:
2.5X10-4 mm Hg at 25 °C, extrapolated from experimentally-derived coefficients
汽化热:
58.3 kJ/mol
电离电位:
7.99 eV
保留指数:
1859;1876;1910.1;316.63;317.43
计算性质
辛醇/水分配系数(LogP):
6
重原子数:
18
可旋转键数:
2
环数:
3.0
sp3杂化的碳原子比例:
0.0
拓扑面积:
0
氢给体数:
0
氢受体数:
0
ADMET
代谢
O-和M-三苯酚的主要代谢物是葡萄糖苷酸和游离酚。
MAJOR METABOLITES OF O- & M-TERPHENYL ARE GLUCOSIDURONIC ACIDS & FREE PHENOLS.
(14)C-LABELED O-TERPHENYL 80 MG/KG, ADMIN INTRAGASTRICALLY TO RATS, ABOUT 10% OF RADIOACTIVITY IN FECES DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, ABOUT 86% IN FREE PHENOLS, REMAINING 4% IN NON-HYDROLYZED, CONJUGATED POLAR METABOLITES.
(14)C-LABELED O-TERPHENYL 80 MG/KG ADMIN INTRAGASTRICALLY TO RABBITS, 12% OF RADIOACTIVITY IN URINE DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, 79% WAS FOUND IN FREE PHENOLS, & REMAINING 9% IN CONJUGATED POLAR METABOLITES.
Depending on the extent to which these compounds are absorbed, the various terphenyls were metabolized to glucuronic acid conjugates and phenol and excreted in the urine of treated rabbits. Following a single 1 gram oral dose of o-, m-, or p-terphenyl, 60% of the o-, 38% of the m-, and a trace of p-terphenyl were detected as their respective glucuronides in the urine. Zero, 15%, and 30% of the o-, m-, and p-terphenyls, respectively, were isolated unchanged in feces.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
暴露途径
该物质可以通过摄入和吸入被身体吸收。
The substance can be absorbed into the body by ingestion and by inhalation.
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)
AN INTRAGASTRIC DOSE OF (14)C LABELED O-TERPHENYL WAS RAPIDLY ABSORBED, DISTRIBUTED, AND ALMOST COMPLETELY EXCRETED WITHIN 48 HR, IN THE RAT MAINLY THROUGH THE BILE AND IN THE RABBIT MAINLY THROUGH URINARY EXCRETION. TEMPORARY ACCUM IN THE LIVER PEAKED AT 4.5 HR IN THE MOUSE AND WAS COMPLETELY CLEARED IN 1 WK.
RADIOACTIVITY FROM (14)C-LABELED O-TERPHENYL (80 MG/KG, INTRAGASTRICALLY) WAS ALMOST COMPLETELY EXCRETED WITHIN 48 HR PRIMARILY VIA BILIARY ROUTE IN RATS & URINARY TRACT IN RABBITS. DURING 1ST 24 HR, RATS EXCRETED 60% & RABBITS 72% OF ADMIN DOSE.
1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.
Cross-Coupling of Triallyl(aryl)silanes with Aryl Bromides and Chlorides: An Alternative Convenient Biaryl Synthesis
作者:Akhila K. Sahoo、Takuro Oda、Yoshiaki Nakao、Tamejiro Hiyama
DOI:10.1002/adsc.200404188
日期:2004.12
give various biaryls in good yields. It is worthwhile to note that the all-carbon-substituted arylsilanes, stable towards moisture, acid, and base and easily accessible, serve as a highly practical alternative to their aryl(halo)silane counterparts. A catalyst system consisting of [(η3-C3H5)PdCl]2 and 2-[2,4,6-(i-Pr)3C6H2]-C6H4PCy2 and use of TBAF⋅3 H2O in THF-H2O are effective especially for the cross-coupling
在DMSO-H 2 O中存在PdCl 2 / PCy 3和氟化四丁基铵(TBAF)的情况下,多种芳基溴化物与三烯丙基(芳基)硅烷的交叉偶联是有效的,以高收率得到各种联芳基。值得一提的是,全碳取代的芳基硅烷对水分,酸和碱稳定,易于获得,可作为其芳基(卤代)硅烷对应物的高度实用替代品。由[(η的催化剂体系3 -C 3 H ^ 5)的PdCl] 2和2- [2,4,6-(我-Pr)3 c ^ 6 ħ 2 ] -C 6 H ^ 4 PCY2和在THF-H 2 O中使用TBAF·3 H 2 O对于与芳基氯的交叉偶联特别有效。两种催化剂体系均能耐受多种常见的官能团。推测反应的高效率归因于用TBAF·3 H 2 O和适量的水处理后烯丙基的易裂解。二烯丙基(二苯基)硅烷还可以与各种芳基溴化物和氯化物交联,收率很高,而烯丙基(三苯基)硅烷只能以中等收率得到交联产物。通过溴氯苯与不同芳基硅烷的顺序交叉偶联,可
Halogen−Metal Exchange in 1,2-Dibromobenzene and the Possible Intermediacy of 1,2-Dilithiobenzene
作者:Holger F. Bettinger、Matthias Filthaus
DOI:10.1021/jo7013033
日期:2007.12.1
The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine−lithium exchange and subsequent
Palladium Membrane-Installed Microchannel Devices for Instantaneous Suzuki-Miyaura Cross-Coupling
作者:Yoichi M. A. Yamada、Toshihiro Watanabe、Tomohiko Beppu、Naoshi Fukuyama、Kaoru Torii、Yasuhiro Uozumi
DOI:10.1002/chem.201000511
日期:——
Instantaneous catalytic carbon–carbon bond‐forming reactions were achieved in catalytic membrane‐installed microchanneldevices that have a polymeric palladium‐complex membrane. The catalytic membrane‐installed microchanneldevices were provided inside the microchannels by means of coordinative and ionic molecular convolution at the interface between the organic and aqueous phases flowing laminarly
The Suzuki−Miyaura cross-coupling of aryl phosphates using Ni(PCy3)2Cl2 as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling
Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance
salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2−. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved
水溶性的 salan 配体是通过对具有连接氮原子的各种桥接单元(接头)的 salens(N,N'-双(亚硅基)乙二胺和类似物)进行氢化和随后的磺化来合成的。Pd (II) 配合物是在硫柳胺和 [PdCl4]2- 的反应中获得的。配体和配合物的表征也包括广泛的 X 射线衍射研究。Pd (II) 配合物被证明是芳基卤化物和芳基硼酸衍生物在 80°C 下在水和空气中的 Suzuki-Miyaura 反应的高活性催化剂。对 Pd (II)-磺胺嘧啶催化剂的比较研究表明,催化活性随着接头长度的增加和配体 N 供体原子周围空间拥挤度的增加而大大增加;最高比活为40,000(mol底物)(mol催化剂×h)-1。