4-溴-2,6-二氯酚 | 3217-15-0

• 物质功能分类: 香精与香料 - 酚类 - 合成香料 - 酚类、醚类和环氧化物
• 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: 4-溴-2,6-二氯酚
• 中文别名: 4-溴-2,6-二氯苯酚2,6-二氯对溴苯酚；2,6-二氯对溴苯酚；4-溴-2,6-二氯苯酚
• 英文名称: 4-bromo-2,6-dichloro-phenol
• 英文别名: 2,6-dichloro-4-bromophenol；2,6-Dichlor-4-brom-phenol；4-Brom-2,6-dichlor-phenol；4-Bromo-2,6-dichlorophenol
• CAS: 3217-15-0
• 化学式: C₆H₃BrCl₂O
• mdl: MFCD00019996
• 分子量: 241.899
• InChiKey: KGURSDWHGSLAPP-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65℃
• 沸点：
  247℃
• 密度：
  1.890
• 闪点：
  103℃
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  6.1
• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在室温环境下，需密封保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2,6-dichlorophenol
Synonyms:

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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-dichlorophenol
CAS number: 3217-15-0

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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, refrigerated.
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: C6H3BrCl2O
Molecular weight: 241.9

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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

制备方法与用途

化学性质
白色结晶或略带粉色的结晶，熔点为66.5℃。该物质易溶于醇和醚，微溶于冷的石油醚，并不溶于水。

用途
作为有机合成中间体使用。

生产方法
由邻氯苯酚经溴化、氯化而得。具体步骤如下：首先将邻氯苯酚溶解在四氯化碳中，在30℃以下搅拌并缓慢滴加溴素，完成后继续搅拌反应2小时。接着，在室温下除去氢溴酸，回收四氯化碳后进行减压蒸馏，收集110-120℃（2kPa）的馏分，得到4-溴-2-氯苯酚。随后将该物质溶解于乙酸中，并在冰冷条件下通入氯气直至不再析出结晶。加热回流使结晶完全溶解后进行脱色、过滤、冷却结晶并再次过滤。最后用石油醚洗涤所得产物，即得成品。

反应信息

• 作为反应物：
  描述：

  4-溴-2,6-二氯酚 在 四(三苯基膦)钯 sodium hydroxide 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.5h， 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：

  4-溴苯酚 在 二氧化碳 、 氯 、 溶剂黄146 作用下， 生成 4-溴-2,6-二氯酚
  参考文献：
  名称：

  Odor Identification Impairments in Schizophrenia: Relationship With Demographic Measures, Clinical Variables, and Diagnostic Subtypes

  摘要：

  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。

  DOI：

  10.1017/s1092852900022252
• 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

• 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
  作者：Kaveh Khosravi、Shirin Naserifar

  DOI：10.1016/j.tet.2018.09.041

  日期：2018.11

  Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α, β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic

  几种氧化方法分别是芳族化合物的硫氰化，烯烃的环氧化，芳族醛的酰胺化，α，β-不饱和酮的环氧化，硫化物氧化为亚砜和砜，拜耳-维格反应，苯胺和苯酚衍生物的溴化和碘化氧化酯化，吡啶氧化和仲，烯丙基和苄基醇的氧化反应均使用1,1,2,2-四氢过氧-1,2-二苯乙烷作为潜在的固体氧化剂进行，可储存数月而不会损失其活性。所有步骤均通过温和的反应条件完成，并以高收率和较短的反应时间提供了产物。
• Macrocyclic MCL-1 inhibitors and methods of use
  申请人：AbbVie Inc.

  公开号：US20190055264A1

  公开（公告）日：2019-02-21

  The present disclosure provides for compounds of Formula (I) wherein A 2 , A 3 , A 4 , A 6 , A 7 , A 8 , A 15 , R A , R 5 , R 9 , R 10A , R 10B , R 11 , R 12 , R 13 , R 14 , R 16 , W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

  本公开提供了Formula (I)的化合物，其中A2、A3、A4、A6、A7、A8、A15、RA、R5、R9、R10A、R10B、R11、R12、R13、R14、R16、W、X和Y具有规范中定义的任何值，以及其药学上可接受的盐，可用作治疗疾病和病况的药物，包括癌症。还提供了包含Formula (I)化合物的药物组合物。
• Sulfamoylheteroaryl pyrazole compounds as anti-inflammatory/analgesic agents
  申请人：PFIZER INC.

  公开号：US20030144280A1

  公开（公告）日：2003-07-31

  This invention relates to a compound of the formula: 1 or a pharmaceutically acceptable salt thereof, wherein A and R 1 are each an optionally substituted 5 to 6-membered heteroaryl, wherein the heteroaryl is optionally fused to a carbocyclic ring or 5 to 6-heteroaryl; R 2 is NH 2 ; R 3 and R 4 are each hydrogen, halo, (C 1 -C 4 )alkyl optionally substituted with halo and the like; and X 1 to X 4 are each hydrogen, halo, hydroxy, (C 1 -C 4 )alkyl optionally substituted with halo and the like. These compounds have COX-2 inhibiting activity and thus useful for treating or preventing inflammation or other COX-2 related diseases.

  本发明涉及一种化合物的公式： 1 或其药用可接受的盐，其中A和R 1 各自为可选地取代的5至6成员的杂芳基，其中杂芳基可选择性熔合至碳环或5至6-杂芳基；R 2 为NH 2 ；R 3 和R 4 各自为氢，卤素，(C 1 -C 4 )烷基可选择性被卤素等取代；和X 1 至X 4 各自为氢，卤素，羟基，(C 1 -C 4 )烷基可选择性被卤素等取代。这些化合物具有COX-2抑制活性，因此可用于治疗或预防炎症或其它COX-2相关疾病。
• [EN] PYRIMIDONE DERIVATIVES AS SELECTIVE CYTOTOXIC AGENTS AGAINST HIV INFECTED CELLS<br/>[FR] DÉRIVÉS DE PYRIMIDONE EN TANT QU'AGENTS CYTOTOXIQUES SÉLECTIFS CONTRE DES CELLULES INFECTÉES PAR LE VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2020131597A1

  公开（公告）日：2020-06-25

  The present disclosure is directed to pyrimidone derivatives of Formula I and their use for selectively killing HIV infected GAG-POL expressing cells without concomitant cytotoxicity to HIV nave cells, and for the treatment or prophylaxis of infection by HIV, or for the treatment, prophylaxis or delay in the onset or progression of AIDS or AIDS Related Complex (ARC).

  本公开涉及式I的嘧啶酮衍生物及其用于选择性杀灭HIV感染的GAG-POL表达细胞而不对HIV天然细胞产生细胞毒性，并用于治疗或预防HIV感染，或用于治疗、预防或延缓艾滋病或艾滋病相关综合症（ARC）的发病或进展。
• Generation of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization
  作者：Paul A. Allegretti、Timothy M. Horton、Yassan Abdolazimi、Hannah P. Moeller、Benjamin Yeh、Matthew Caffet、Guillermina Michel、Mark Smith、Justin P. Annes

  DOI：10.1016/j.bmc.2019.115193

  日期：2020.1

  current lead compounds have inadequate cellular potency for in vivo application. Herein, we report the clinical stage anti-cancer kinase inhibitor OTS167 as a structurally novel, remarkably potent DYRK1A inhibitor and inducer of human β-cell replication. Unfortunately, OTS167's target promiscuity and cytotoxicity curtails utility. To tailor kinase selectivity towards DYRK1A and reduce cytotoxicity we designed

  小分子刺激 β 细胞再生已成为一种有前途的糖尿病治疗策略。尽管双特异性酪氨酸磷酸化调节激酶 1A (DYRK1A) 的化学抑制足以增强 β 细胞复制，但目前的先导化合物对于体内应用的细胞效力不足。在此，我们报告临床阶段抗癌激酶抑制剂 OTS167 是一种结构新颖、非常有效的 DYRK1A 抑制剂和人类 β 细胞复制诱导剂。不幸的是，OTS167 的靶标混杂和细胞毒性限制了实用性。为了调整对 DYRK1A 的激酶选择性并降低细胞毒性，我们根据 DYRK1A-OTS167 复合物的建模结构设计了一个包含 51 种 OTS167 衍生物的库。事实上，衍生物表征产生了几种具有出色的 DYRK1A 抑制和人类 β 细胞复制促进功效但显着降低细胞毒性的先导化合物。这些化合物是迄今为止描述的最有效的人类 β 细胞复制促进化合物，并举例说明了有目的地利用高级化合物的脱靶活性来实现所需应用的潜力。