2,5-二溴苯酚 | 28165-52-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,5-二溴苯酚
• 中文别名: 2,4-二氯苯甲酰氯
• 英文名称: 2,5-dibromophenol
• 英文别名: 2,5-DBP
• CAS: 28165-52-8
• 化学式: C₆H₄Br₂O
• 分子量: 251.905
• InChiKey: GUXWVUVLXIJHQF-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  244.6±20.0 °C(Predicted)
• 密度：
  2.095±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 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

• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,5-Dibromophenol
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: 2,5-Dibromophenol
CAS number: 28165-52-8

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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: C6H4Br2O
Molecular weight: 251.9

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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 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

理化性质

2,5-二溴苯酚是一种白色至淡黄色粉末状的有机化合物，微溶于水，但可以稍微溶解在氯仿和甲醇中。为了保持其稳定性，它应储存在惰性气氛和室温下。

用途

2,5-二溴苯酚的化学结构中含有两个溴原子，在有机合成中作为重要的中间体，常用于合成其他复杂的有机分子。

合成

将1080克2,5-二溴苯甲醚与5500毫升DMF加入反应容器中。搅拌的同时，控制温度在80-100°C下分批加入688克三氯化铝。通过气相色谱仪跟踪直到反应结束。反应完成后，加入二氯乙烷和水，将混合物分离。油相用水洗涤并分离，所得油相脱溶剂后得到黄色固体2,5-二溴苯酚，总重量为548克，纯度为98%，收率为53.3%。

反应信息

• 作为反应物：
  描述：

  2,5-二溴苯酚 在 sodium nitrate 、 alkaline aqueous NaOBr 、 硫酸 、 1,2-二氯乙烷 、 sodium nitrite 作用下， 生成 3,4,6-三溴-2-硝基苯酚
  参考文献：
  名称：

  250.间溴酚的直接二溴化和族群迁移的一个例子

  摘要：

  DOI：

  10.1039/jr9330001053
• 作为产物：
  描述：

  1,4-二溴苯 在 水 、 三乙胺 、 三氟乙酸 作用下， 生成 2,5-二溴苯酚
  参考文献：
  名称：

  阳极氧化选择性和一锅法形成苯酚

  摘要：

  通过阳极氧化成功地完成了苯和取代苯的直接单羟基化反应，从而以良好的收率形成了相应的苯酚衍生物。阳极氧化通常在三氟乙酸和含有三乙胺的二氯甲烷的混合溶剂中，使用配备有铂板作为阳极，碳棒作为阴极的分隔式电池进行。具有吸电子基团的苯衍生物适用于本发明的电化学氧化。澄清的是，由自由基阳离子反应形成的初始产物形成了芳基三氟乙酸酯，该自由基阳离子是由一个电子从底物转移到三氟乙酸中，然后在后处理过程中进行水解而得到相应的酚。

  DOI：

  10.1016/s0040-4020(96)00056-7

文献信息

• Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions
  作者：Sebastian B. Beil、Timo Müller、Sydney B. Sillart、Peter Franzmann、Alexander Bomm、Michael Holtkamp、Uwe Karst、Wolfgang Schade、Siegfried R. Waldvogel

  DOI：10.1002/anie.201712718

  日期：2018.2.23

  and powerful active anode system that can be operated in 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) has been discovered. In HFIP the molybdenum anode forms a compact, conductive, and electroactive layer of higher‐valent molybdenum species. This system can replace powerful but stoichiometrically required MoV reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable

  发现了一种可以在1,1,1,3,3,3-六氟-2-丙醇（HFIP）中运行的功能强大的新型阳极活性系统。在HFIP中，钼阳极形成一个高价钼物种的致密，导电和电活性层。该系统可替代功能强大但化学计量上要求的Mo V试剂，用于芳基的脱氢偶联。这种电解反应是更可持续的，并允许转化广泛范围的活化芳烃。
• COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM
  申请人：Whitten Jeffrey P.

  公开号：US20110263612A1

  公开（公告）日：2011-10-27

  Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of store-operated calcium (SOC) channels. Also described herein are methods of using such SOC channel modulators, alone and in combination with other compounds, for treating diseases or conditions that would benefit from inhibition of SOC channel activity.

  本文描述了含有这些化合物的化合物和药物组合物，这些化合物调节储存操作钙（SOC）通道的活性。本文还描述了使用这种SOC通道调节剂的方法，单独或与其他化合物结合，用于治疗需要抑制SOC通道活性的疾病或症状。
• 有机电致发光化合物、有机电致发光器件及其应用
  申请人：南京高光半导体材料有限公司

  公开号：CN108164544A

  公开（公告）日：2018-06-15

  本发明提供了有机电致发光化合物、有机电致发光器件及其应用。本发明有机电致发光化合物结构如下：其可作为空穴传输层材料、电子阻隔层材料、电子传输层或空穴组隔层材料而应用于有机电致发光器件中，能够有效降低器件的驱动电压，提高发光效率、亮度、热稳定性、色彩纯度及器件寿命。同时，本发明有机电致发光器件具有驱动电压低，发光效率高、亮度高、热稳定性好、色彩纯度高及器件寿命长等优点。
• DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1002/anie.200905544

  日期：2010.1.18

  Palladium catalysts bearing dihydroxyterphenylphosphine ligands (such as 1) are reported for the ortho‐selective cross‐coupling of Grignard reagents and dihaloarenes. The second hydroxy group onto the terphenylphosphine ligand dramatically improved the catalytic efficiency and expanded the scope of the reaction.

  据报道，带有二羟基三苯膦配体（如1）的钯催化剂可用于格氏试剂和二卤代芳烃的邻位选择性交叉偶联。三苯基膦配体上的第二个羟基大大提高了催化效率并扩大了反应范围。
• [EN] METHYLAMINE DERIVATIVES AS LYSYSL OXIDASE INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE LA MÉTHYLAMINE COMME INHIBITEURS DE LA LYSYL OXIDASE POUR LE TRAITEMENT DU CANCER
  申请人：THE INST OF CANCER RESEARCH: ROYAL CANCER HOSPITAL

  公开号：WO2017141049A1

  公开（公告）日：2017-08-24

  Provided are compounds of the Formula (I), or a pharmaceutically acceptable salt thereof, wherein W, X, Y, Z, x, R1, R2, R3, x and n are defined in the specification. The compounds are inhibitors of lysyl oxidase (LOX) and lysyl oxidase-like (LOXL) family members (LOXL1, LOXL2, LOXL3, LOXL4) and are useful in therapy, particularly in the treatment of cancer. Also disclosed are LOX inhibitors for use in the treatment of a cancer associated with EGFR and biomarkers that predict responsiveness to a LOX inhibitor.

  提供的是Formula (I)的化合物，或其药用可接受的盐，其中W、X、Y、Z、x、R1、R2、R3、x和n在规范中有定义。这些化合物是赖氨酸氧化酶（LOX）和赖氨酸氧化酶样（LOXL）家族成员（LOXL1、LOXL2、LOXL3、LOXL4）的抑制剂，并且在治疗中很有用，特别是在癌症治疗中。还披露了用于治疗与EGFR相关的癌症的LOX抑制剂，以及预测对LOX抑制剂响应性的生物标志物。