异丙基联苯 | 25640-78-2

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 异丙基联苯
• 英文名称: 2-isopropylbiphenyl
• 英文别名: 2-isopropyl-1,1'-biphenyl；Isopropylbiphenyl；1-phenyl-2-propan-2-ylbenzene
• CAS: 25640-78-2
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: HKTCLPBBJDIBGF-UHFFFAOYSA-N

物化性质

• 熔点：
  9.83°C (estimate)
• 沸点：
  293.19°C (estimate)
• 密度：
  0.9811 (estimate)
• LogP：
  5.33 at 20℃
• 颜色/状态：
  Water white
• 溶解度：
  In water = 0.6 mg/l at 25 °C
• 蒸汽压力：
  5.0X10-4 mm Hg at 25 °C
• 粘度：
  At 37.8 °C = 5.8 sq mm/s
• 折光率：
  Refractive index = 1.5798
• 保留指数：
  1500;1512

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

对几种物种，包括人类在内，对异丙基联苯的代谢进行了广泛的研究，主要采用了气相色谱-质谱法。发现的复杂代谢物序列对于每个研究的物种（大鼠、狗、猴子、人类）都是不同的。每个物种中的代谢物模式与该物种的药理和毒理学特性一致。代谢物模式是顺序氧化的结果，始于狗和人类中对异丙基基团在三级碳上的羟基化，以及大鼠和猴子中在三级和一级碳上的羟基化。

AN EXTENSIVE STUDY OF THE METABOLISM OF ISOPROPYLBIPHENYL IN SEVERAL SPECIES, INCLUDING MAN, WAS ACCOMPLISHED BY EXTENSIVE USE OF GAS CHROMATOGRAPHY-MASS SPECTROMETRY. THE COMPLEX METABOLITE SEQUENCES FOUND WERE DIFFERENT FOR EACH SPECIES STUDIED (RAT, DOG, MONKEY, MAN). METABOLITE PATTERNS IN EACH SPECIES WERE CONSISTENT WITH THE PHARMACOLOGICAL & TOXICOLOGICAL PROPERTIES IN THAT SPECIES. METABOLITE PATTERNS WERE A CONSEQUENCE OF SEQUENTIAL OXIDATION BEGINNING WITH HYDROXYLATION OF THE ISO-PROPYL GROUP AT THE TERTIARY CARBON IN DOG & MAN & AT BOTH THE TERTIARY & PRIMARY CARBON IN RAT & MONKEY.

来源:Hazardous Substances Data Bank (HSDB)

代谢

给予大鼠口服或腹腔注射标记有(14)C的4-异丙基联苯（25毫克/千克）后，大鼠在粪便中排出的(14)C比尿液中多，并且在48小时后在尸体中保留了12.1%-16.1%的剂量。(14)C在48小时内在检查的所有组织中都能观察到，但在脂肪中异常高。血浆中的主要代谢物是联苯丙酸，还有少量的联苯-2-丙醇和联苯-α-甲基乙醇酸。尿液和胆汁中的代谢物主要是血浆代谢物的环羟基化形式，所有酚类代谢物都是结合形式的。...将4-异丙基联苯与大鼠肝脏15000克上清液孵化，产生了联苯-2-丙醇和联苯-α-甲基乙醇酸。

RATS GIVEN (14)C-LABELED 4-ISOPROPYLBIPHENYL (25 MG/KG, ORALLY OR IP) EXCRETED MORE (14)C IN FECES THAN IN URINE & RETAINED 12.1%-16.1% OF DOSE IN THE CARCASS AFTER 48 HR. (14)C WAS OBSERVED IN ALL TISSUES EXAMINED AT 48 HR, BUT WAS UNUSUALLY HIGH ONLY IN FAT. THE MAIN METABOLITE IN PLASMA WAS BIPHENYLPROPIONIC ACID, WITH SMALL AMOUNTS OF BIPHENYL-2-PROPANOL & BIPHENYL-ALPHA-METHYL GLYCOLIC ACID. METABOLITES IN URINE & BILE WERE MAINLY RING-HYDROXYLATED FORMS OF THE PLASMA METABOLITES, & ALL THE PHENOLIC METABOLITES WERE CONJUGATED. ... INCUBATION OF 4-ISOPROPYLBIPHENYL WITH RAT LIVER 15,000 G SUPERNATANT YIELDED BIPHENYL-2-PROPANOL & BIPHENYL-ALPHA-METHYL GLYCOLIC ACID.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：异丙基联苯是一种白色溶液，可溶于水。它用于无碳复写纸系统，替代电容器中的多氯联苯（PCBs）和热传递流体。它用作高压电容器中的溶剂，并作为兽药控制炎症。这种化学物质改善了磨损性能，并在用作润滑剂时提供辐射抵抗。它被用作溶剂。 人类暴露和毒性：处理自复制纸张表格的女性办公室工作人员报告了难闻的气味、头痛、刺激、疲劳以及面部和眼睛发红。这种气味归因于异丙基联苯溶剂的释放。办公室工作人员表示，仅眼睛和呼吸道刺激是由含有这种化学物质的无碳复写纸引起的，这些症状最为常见。再次强调，用脱敏墨水处理的CPP与皮肤刺激有关。它对磨损的皮肤有轻微刺激作用，对完整的皮肤有轻微刺激作用。 动物研究：当大鼠口服这种化学物质10到15天时，会导致中性粒细胞减少、淋巴细胞增多和低蛋白血症，肝脏和肾脏营养不良，脾脏增生和心肌纤维肥大。大鼠吸入这种化合物会在暴露期间和暴露后立即导致梳理行为和轻微的抑郁。尸检没有发现明显的异常。

IDENTIFICATION AND USE: Isopropyl biphenyl is a white solution, soluble in water. It is used in carbonless-copy paper systems, replaces PCBs in capacitors, and heat transfer fluids. It is used a s a solvent in high voltage capacitors, and as a veterinary medicine to control inflammation. This chemical improves wear properties, and provides radiation resistance when used in lubricants. It is used as a solvent. HUMAN EXPOSURE AND TOXICITY: Complaints of an unpleasant smell, headaches, irritation, fatigue and redness of the face and eyes were reported in female office workers handling self- copying paper forms. The smell was attributed to the release of isopropyl biphenyl solvent. Office workers indicated only eye, and respiratory tract irritation caused by carbonless copy paper containing this chemical was most often associated with symptoms. Again, CPP treated with desentizing ink were associated with skin irritation. It is a mild irritant on abraded skin, slight irritant on intact skin. ANIMAL STUDIES: When administered to rats orally this chemical for 10 to 15 days caused neutropenia, lymphocytosis, and hypoproteinemia, dystrophy of the liver and kidneys, hyperplasia of the spleen and hypertrophy of myocardial fibers. Inhalation of this compound by rats caused grooming and slight depression during and immediately after exposure. Necropsy showed no gross anomalies.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 人类毒性摘录

13名处理自动复印纸表格的女性办公室工作人员中有9人报告称出现了不愉快的气味、头痛、刺激、疲劳以及面部和眼睛发红。这种气味被归因于异丙基联苯溶剂的释放。

Complaints of an unpleasent smell, headaches, irritation, fatigue and redness of the face and eyes were reported in 9 out of 13 female office workers handling self-copying paper forms. The smell was attributed to the release of isopropylbiphenyl solvent.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

5篇关于该主题论文的结论：对80名办公室工作人员的研究表明，无碳复写纸（CCP）仅导致眼睛和呼吸道刺激。用脱敏油墨处理的纸张在统计学上与皮肤刺激有关。研究了273个纸张样本，其中190个是无碳的。含单异丙基联苯的纸张最常与症状有关。同样，用脱敏油墨处理的CPP与皮肤刺激有关。研究了环境条件。没有发现无碳复写纸挥发的溶剂浓度与刺激性症状发生之间的相关性。研究了甲醛、戊二醛和溶解显色剂的有机溶剂在标准条件下的情况。无碳复写纸排放的醛类太少，不足以引起刺激性症状。最高排放的是煤油，这与症状无关。

Conclusions of 5 papers on the subject: Studies in 80 office workers indicated only eye and respiratory tract irritation caused by carbonless copy paper (CCP). Papers treated with desensitizing ink were statistically associated with skin irritation. 273 paper samples were studied, 190 of which were carbonless. Paper containing monoisopropylbiphenyl was most often associated with symptoms. Again, CPP treated with desentizing ink were associated with skin irritation. Environmental conditions were studied. No correlations were found between airborne solvent concentrations from CPP and the occurrence of irritative symptoms. Formaldehyde, glutaraldehyde and the organic solvents in which the color formers are dissolved were studied under standard contitions. The emission of aldehydes from CPP is too low to cause the irritative symptoms. The highest emission was of kerosene, which could not be related to the symptoms. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

当以800毫克/千克/天的剂量连续给药10-15天时，异丙基联苯会导致中性粒细胞减少、淋巴细胞增多、低蛋白血症、肝脏和肾脏营养不良、脾脏增生以及心肌纤维肥大。

WHEN ADMIN ORALLY TO RATS, THE LD50 VALUE OF ISOPROPYLDIPHENYL WAS 8.5 G/KG. WHEN ADMIN AT 800 MG/KG/DAY FOR 10-15 DAYS, ISOPROPYLDIPHENYL CAUSED NEUTROPENIA, LYMPHOCYTOSIS, HYPOPROTEINEMIA, DYSTROPHY OF THE LIVER & KIDNEYS, HYPERPLASIA IN THE SPLEEN, & HYPERTROPHY IN MYOCARDIAL FIBERS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

给予老鼠含有放射性碳-14标记的4-异丙基联苯（25毫克/千克，口服或腹腔注射）后，在粪便中排出的放射性碳-14比尿液中多，并且在48小时后在尸体中保留了12.1%-16.1%的剂量。在48小时时检查的所有组织中都观察到了放射性碳-14，但在脂肪中的含量异常高。

RATS GIVEN (14)C-LABELED 4-ISOPROPYLBIPHENYL (25 MG/KG, ORALLY OR IP) EXCRETED MORE (14)C IN FECES THAN IN URINE & RETAINED 12.1%-16.1% OF DOSE IN THE CARCASS AFTER 48 HR. (14)C WAS OBSERVED IN ALL TISSUES EXAMINED AT 48 HR, BUT WAS UNUSUALLY HIGH ONLY IN FAT.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  异丙基联苯 在 三氯化铝 、 异丙苯 、 苯 作用下， 反应 7.0h， 生成 4-异丙基联苯
  参考文献：
  名称：

  烷基联苯异构转化的平衡

  摘要：

  摘要 研究了液相中单、二和三烷基联苯 ( abp ) 相互转化的平衡，温度为 308 至 423 K。根据实验平衡常数，ΔrHmo/(kJ·mol−1) 值和ΔrSmo/(J·K-1·mol-1)被计算。下面分别给出：Et-bp (I)、i-Pr-bp (II) 和 t-Bu-bp (III) 的反应、化合物和值： 4- abp = 3- abp , I, 0.23, 5.76 ; 二、(0.45±0.41)、(5.72±1.13)；三、(0.48±0.53)、(4.83±0.53)；2- abp = 4- abp , I, -3.3, -5.76; II、-12.6、-5.76；III、-15.4、-5.76；3,5-di-abp = 3,3'-di-abp, I, -0.1, 5.76; 二、(0±0.60)、(5.98±1.65)；三、(-1.34±0.67)、(4.48±1.87)；3

  DOI：

  10.1016/0021-9614(87)90137-6
• 作为产物：
  描述：

  2-(biphenyl-2-yl)-2-propanol 在 aluminum oxide 、 乙醇 、 镍 、 甲苯 作用下， 100.0~325.0 ℃ 、9.81 MPa 条件下， 生成 异丙基联苯
  参考文献：
  名称：

  Dicyclic Hydrocarbons. I. 2-Aklylbiphenyls

  摘要：

  DOI：

  10.1021/ja01163a075

文献信息

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• Trineopentylphosphine: A Conformationally Flexible Ligand for the Coupling of Sterically Demanding Substrates in the Buchwald–Hartwig Amination and Suzuki–Miyaura Reaction
  作者：Steven M. Raders、Jane N. Moore、Jacquelynn K. Parks、Ashley D. Miller、Thomas M. Leißing、Steven P. Kelley、Robin D. Rogers、Kevin H. Shaughnessy

  DOI：10.1021/jo400435z

  日期：2013.5.17

  palladium provides a highly effective catalyst for the Buchwald–Hartwig coupling of sterically demanding aryl bromides and chlorides with sterically hindered aniline derivatives. Excellent yields are obtained even when both substrates include 2,6-diisopropyl substituents. Notably, the reaction rate is inversely related to the steric demand of the substrates. X-ray crystallographic structures of Pd(TNpP)2,

  三叔戊基膦（TNpP）与钯的结合为空间受限的芳族溴化物和氯化物与空间受阻的苯胺衍生物的布赫瓦尔德-哈特维格偶联提供了一种高效的催化剂。即使两个底物都包含2，6-二异丙基取代基，也可获得优异的产率。值得注意的是，反应速率与底物的空间需求成反比。Pd（TNpP）2，[Pd（4- t -Bu-C 6 H 4）（TNpP）（μ-Br）] 2和[Pd（2-Me-​​C 6 H 4）的X射线晶体结构（TNpP）（μ-Br）] 2被报道。这些结构表明，TNpP配体的构象柔韧性在允许催化剂偶联受阻底物方面起着关键作用。Pd / TNpP系统对受阻芳基溴化物的Suzuki偶联也显示出良好的活性。
• Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions
  作者：Clovis Peter、Antoine Derible、Jean-Michel Becht、Julien Kiener、Claude Le Drian、Julien Parmentier、Vanessa Fierro、Maria Girleanu、Ovidiu Ersen

  DOI：10.1039/c4ta06478j

  日期：——

  worm-like mesoporous network limiting palladium leaching while keeping good access to the reactants. It was successfully used as a catalyst for ligand-free Suzuki–Miyaura couplings of aryl bromides in a green solvent (propane-1,2-diol) in the presence of extremely low amounts of supported palladium (usually 30 μequiv.). It is noteworthy that almost palladium-free products (containing less than 1.5 μequiv

  一种简单，直接，环保的一锅法，它由廉价，无害且易于获得的生物聚合物（单宁）作为碳前体，由Pluronic®F127表面活性剂作为孔隙来制备含钯的中孔碳（Pd @ MC）据报道有结构化剂和钯盐。这种材料具有使钯纳米粒子陷入不规则的空隙中的独特之处，该空隙与蠕虫状的中孔网络相连，从而限制了钯的浸出，同时又保持了与反应物的良好通道。在存在极少量负载的钯（通常为30μequiv。）的情况下，它已成功地用作绿色溶剂（丙烷-1,2-二醇）中无配体的芳基溴化物的Suzuki-Miyaura偶联剂的催化剂。值得一提的是，几乎可以获得不含钯的产品（贵金属含量少于1.5μequiv。）。
• Photoelectric properties of aromatic triangular tri-palladium complexes and their catalytic applications in the Suzuki–Miyaura coupling reaction
  作者：Xujun Li、Jia Li、Xiaoshuang Wang、Lingang Wu、Yanlan Wang、Giovanni Maestri、Max Malacria、Xiang Liu

  DOI：10.1039/d1dt01597d

  日期：——

  The photoelectric properties and catalytic activities of substituted triphenylphosphine and sulfur/selenium ligand supported aromatic triangular tri-palladium complexes 1–4, abbreviated as [Pd3]+, were investigated. The cyclic voltammogram of [Pd3]+ in CH3CN-nBu4NPF6 showed a single quasi-reversible wave which was consistent with their robust property and provided preliminary proof for their electron

  研究了取代的三苯基膦和硫/硒配体负载的芳族三角三钯配合物1-4的光电性能和催化活性，缩写为 [Pd 3 ] +。[Pd 3 ] +在CH 3 CN- n Bu 4 NPF 6 中的循环伏安图显示出单一的准可逆波，这与其稳健的性质一致，并为其催化中的电子转移过程提供了初步证据。在 267 nm 激发下，[Pd 3 ] +在 77 K 至 287 K 的温度梯度下，在 550 和 780 nm 处表现出强烈的比率荧光。这些特殊的三角形三钯配合物在 Suzuki-Miyaura 偶联反应中显示出优异的催化活性和与芳基碘化物的专属反应性，而不是其他卤代芳烃。研究了取代基对芳基碘化物和芳基硼​​酸（包括吡啶、吡嗪和噻吩等杂芳烃）的电子和空间位阻效应，大多数底​​物的产率高达 99%。(2-[1,1'-联苯]-2-基苯并噻唑)与选择性环氧合酶-2 (COX-2)抑制剂类似，也用我们的三钯催化剂合成，并得到良好的分离产率（94%）。3
• Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
  作者：Carlos Vila、Massimo Giannerini、Valentín Hornillos、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1039/c3sc53047g

  日期：——

  Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C–C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

  钯催化的二级C(sp3)有机金属试剂交叉偶联反应一直是有机合成中的一个长期挑战，主要由于与不期望的异构化或还原产物形成相关的问题。基于我们最近开发的与有机锂试剂的催化C–C键形成反应，本文呈现了一种钯催化的二级烷基锂试剂与芳基和烯基溴化物的交叉偶联反应。该反应在室温下进行，反应时间短，选择性和产率均很高。这一方法也适用于受阻的芳基溴化物，而这在金属催化的交叉偶联反应中是一个主要挑战。