4-溴-2,6-二氯苯甲醚 | 19240-91-6

• 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: 4-溴-2,6-二氯苯甲醚
• 英文名称: 4-bromo-2,6-dichloroanisole
• 英文别名: 2,6-dichloro-4-bromoanisole；5-bromo-1,3-dichloro-2-methoxybenzene
• CAS: 19240-91-6
• 化学式: C₇H₅BrCl₂O
• 分子量: 255.926
• InChiKey: OAYSFAKCFYRCRU-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69℃
• 沸点：
  250-255℃ (765 Torr)
• 密度：
  1.666±0.06 g/cm3(Predicted)
• 溶解度：
  soluble in No data available
• 保留指数：
  1427

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2,6-dichloroanisole
Synonyms: 5-Bromo-1,3-dichloro-2-methoxybenzene

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-2,6-dichloroanisole
CAS number: 19240-91-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H5BrCl2O
Molecular weight: 255.9

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴-2,6-二氯苯甲醚 在 四(三苯基膦)钯 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 4-羟基-3,5-二氯联苯
  参考文献：
  名称：

  Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling

  摘要：

  An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB, congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(01)00052-2
• 作为产物：
  描述：

  2,6-二氯苯酚 在 溴 、 potassium carbonate 、 sodium sulfite 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 4-溴-2,6-二氯苯甲醚
  参考文献：
  名称：

  BORON-CONTAINING SMALL MOLECULES

  摘要：

  这项发明提供了新颖的化合物，使用这些化合物的方法，以及包含这些化合物的药物配方。

  公开号：

  US20130131016A1
• 作为试剂：
  描述：

  4-溴-2,6-二氯酚 、 potassium carbonate 、 碘甲烷 、 在 4-溴-2,6-二氯酚 、 水 、 乙酸乙酯 、 Sodium sulfate-III 、 4-溴-2,6-二氯苯甲醚 、 silica gel 、 EtOAc petroleum ether 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以to give crude 5-bromo-1,3-dichloro-2-methoxybenzene, which的产率得到4-溴-2,6-二氯苯甲醚
  参考文献：
  名称：

  BORON-CONTAINING SMALL MOLECULES

  摘要：

  这项发明提供了新的化合物，使用这些化合物的方法，以及包含这些化合物的药物配方。

  公开号：

  US20160000813A1

文献信息

• Proton Mobility in 2-Substituted 1,3-Dichlorobenzenes: “ortho” or “meta” Metalation?
  作者：Manfred Schlosser、Christophe Heiss、Elena Marzi、Rosario Scopelliti

  DOI：10.1002/ejoc.200600350

  日期：2006.10

  Nine 1,3-dichlorobenzene congeners were selected as model compds. to assess the relative rates of proton abstraction from 4- and 5-positions ("ortho" vs. "meta" metalation). Using lithium 2,2,6,6-tetramethylpiperidide as the basic reagent, the chlorine-adjacent 4-position underwent metalation exclusively. In contrast, attack at the chlorine-remote 5-position became significant even in the case of moderately

  选择九个 1,3-二氯苯同系物作为模型化合物。评估从 4 位和 5 位（“邻位”与“元”金属化）提取质子的相对速率。使用 2,2,6,6-四甲基哌啶锂作为碱性试剂，4 位氯附近专门进行金属化。相比之下，当使用仲丁基锂时，即使在中等大小的 2-取代基（如二甲氨基或乙基）的情况下，对氯远程 5-位的攻击也变得显着。“邻位/对位”(4-/5-) 比率范围为 80:20 至 65:35。与碳取代基相反，硅更显着的“元取向”效应可归因于芳族的 pi 极化的不同。戒指。[在 SciFinder (R) 上]
• Diflunisal Analogues Stabilize the Native State of Transthyretin. Potent Inhibition of Amyloidogenesis
  作者：Sara L. Adamski-Werner、Satheesh K. Palaninathan、James C. Sacchettini、Jeffery W. Kelly

  DOI：10.1021/jm030347n

  日期：2004.1.1

  observed for 26 of the compounds. Of those, eight exhibited excellent binding selectivity for TTR in human plasma (binding stoichiometry >0.50, with a theoretical maximum of 2.0 inhibitors bound per TTR tetramer). Biophysical studies reveal that these eight inhibitors dramatically slow tetramer dissociation (the rate-determining step of amyloidogenesis) over a duration of 168 h. This appears to be achieved

  合成了FDA批准的非甾体抗炎药diflunisal的类似物，并将其评估为转甲状腺素蛋白（TTR）聚集（包括淀粉样蛋白原纤维形成）的抑制剂。对于26种化合物观察到高抑制活性。其中，八种在人血浆中对TTR表现出优异的结合选择性（结合化学计量比> 0.50，每个TTR四聚体理论上最多结合有2.0种抑制剂）。生物物理研究表明，这八种抑制剂可在168小时的时间内显着减慢四聚体的解离（淀粉样蛋白生成的速率决定步骤）。这似乎是通过基态稳定化来实现的，这提高了四聚体解离的动力学势垒。这八种抑制剂对WT TTR的动力学稳定作用进一步得到证实，淀粉样蛋白原纤维形成的速率随抑制剂浓度（pH 4.4）的增加而降低。TTR.18（2）和TTR.20（2）配合物的X射线共晶体结构揭示了18和20在TTR结合位点以相反的方向结合。将氟从18的间位移至20的邻位可逆转结合方向，使20的亲水性芳环在外部结合袋中取向，其中羧
• Novel Terphenyls as Selective Cyclooxygenase-2 Inhibitors and Orally Active Anti-inflammatory Agents
  作者：James J. Li、Monica B. Norton、Emily J. Reinhard、Gary D. Anderson、Susan A. Gregory、Peter C. Isakson、Carol M. Koboldt、Jaime L. Masferrer、William E. Perkins、Karen Seibert、Yan Zhang、Ben S. Zweifel、David B. Reitz

  DOI：10.1021/jm950878e

  日期：1996.1.1

  The sulfonamide analogs 17 and 21 were found to be much more potent COX-2 inhibitors and orally active anti-inflammatory agents than the corresponding methyl sulfone analogs 16 and 20, respectively, albeit with some decrease in COX-2 selectivity. Structure-activity relationship studies have determined that incorporation of two fluorine atoms in the central phenyl group, as in 20 and 21, is extremely

  一系列新的三联苯甲基砜和磺酰胺已被证明是高效的选择性环氧合酶2（COX-2）抑制剂。发现磺酰胺类似物17和21分别比相应的甲基砜类似物16和20更有效的COX-2抑制剂和口服活性抗炎药，尽管COX-2选择性有所降低。结构-活性关系研究已经确定，在中央苯基中引入两个氟原子（如20和21）对于体外COX-2的效力和选择性以及体内活性都极为有利。1,2-二芳基-4,5-二氟苯磺酰胺系列中几个值得注意的例子是21a-c，k，l，n（COX-2，IC50 = 0.002-0.004 microM），其中所有都具有体外COX-1 / COX-2选择性>1000。此外，在炎症的气袋模型中，磺酰胺21a，b，d，g，j，m，n，q显示出大大增强的口服活性，并抑制了90％以上的前列腺素E2产生。此外，在大鼠佐剂诱导的关节炎模型（ED50 = 0.05 mg / kg）和角叉菜胶诱导的痛觉过敏试验（ED50 =
• Odor Identification Impairments in Schizophrenia: Relationship With Demographic Measures, Clinical Variables, and Diagnostic Subtypes
  作者：Eliza Coleman、Raymond R. Goetz、David Leitman、Scott Yale、Ariel Stanford、Jack M. Gorman、Dolores Malaspina

  DOI：10.1017/s1092852900022252

  日期：2002.1

  Smell identification deficits are consistently found in schizophrenia (SZ), but little is known about the nature and characterization of this deficit or its relationship to the phenomenology of the illness. This study aims to further delineate smell identification errors in SZ by examining the relationship of patient demographic differences with smell-identification performance. Our results showed that a patient's gender and education were related to odor-identification scores, with better performance seen in female patients and in those with greater educational attainment. However, there was no effect related to age, ethnicity, or socioeconomic status on odor identification. A smell identification deficit was also unrelated to clinical characteristics of the patients, including age at first hospitalization, number of psychiatric hospitalizations, and duration of illness. Odor identification also did not differ by SZ subtype, nor between SZ and schizoaffective disorder patients. These findings emphasize that odor identification deficits in SZ are unrelated to clinical illness features, cannot be explained by other confounds related to olfaction in the general population, and may be core features related to the SZ disease process.

  摘要精神分裂症（SZ）患者一直存在嗅觉识别缺陷，但人们对这种缺陷的性质和特征及其与疾病现象学的关系知之甚少。本研究旨在通过研究患者的人口统计学差异与气味识别能力之间的关系，进一步界定精神分裂症患者的气味识别错误。我们的研究结果表明，患者的性别和教育程度与气味识别得分有关，女性患者和教育程度较高的患者的气味识别得分更高。然而，年龄、种族或社会经济地位对气味识别没有影响。气味识别缺陷也与患者的临床特征无关，包括首次住院的年龄、精神病住院次数和病程。气味识别能力也不因精神分裂症亚型而异，也不因精神分裂症患者和精神分裂情感障碍患者而异。这些研究结果强调，SZ患者的气味识别障碍与临床疾病特征无关，不能用普通人群中与嗅觉有关的其他混杂因素来解释，而且可能是与SZ疾病过程有关的核心特征。
• Organophotochemical S_N Ar Reactions of Mildly Electron-Poor Fluoroarenes
  作者：Thomas Sheridan、Hatice G. Yayla、Yajing Lian、Julien Genovino、Nat Monck、Jonathan W. Burton

  DOI：10.1002/ejoc.202000337

  日期：2020.5.14

  C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron‐poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products.

  使用多种醇和吡唑亲核试剂实现了芳烃的CF功能化，而无需金属催化剂或电子贫乏的底物。在蓝色LED光线照射下，用醇或吡唑和DDQ处理氟代芳烃可提供相应的取代产物。