4-溴邻苯二酚 | 17345-77-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-溴邻苯二酚
• 中文别名: 4-溴-1,2-苯二酚；4-溴苯邻二酚；4-溴-1,2-二羟基苯；3,4-二羟基溴苯；4-溴-1,2-苯二醇
• 英文名称: 1-bromo-3,4-dihydroxybenzene
• 英文别名: 4-bromocatechol；4-bromobenzene-1,2-diol
• CAS: 17345-77-6
• 化学式: C₆H₅BrO₂
• 分子量: 189.008
• InChiKey: AQVKHRQMAUJBBP-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  280.5±20.0 °C(Predicted)
• 密度：
  1.844±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温，惰性气体氛围

SDS

4-Bromocatechol Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 4-Bromocatechol

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
Pictograms or hazard symbols
Signal word Warning
Hazard statement Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): 4-Bromocatechol
Percent: >98.0%(GC)
CAS Number: 17345-77-6
Synonyms: 4-Bromo-1,2-dihydroxybenzene
Chemical Formula: C6H5BrO2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
4-Bromocatechol

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: crystal - powder
Color: Slightly pale yellow - Reddish yellow
Odor: No data available
pH: No data available
4-Bromocatechol

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Melting point/freezing point:87 °C
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
No data available
Upper:
Density: No data available
Soluble in : Methanol
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not Listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
4-Bromocatechol

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：

• 白色晶体，熔点为87℃，能溶于乙醇和丙酮，微溶于水。

用途： 主要用于有机合成中间体。

生产方法： 将邻苯二酚溶解在冰乙酸中，然后在冷却条件下滴加溴与冰乙酸配制的溶液。反应2小时后，减压蒸馏除去乙酸，得到粗品。再用溶剂溶解、活性炭脱色，分离、干燥后，即可获得成品。

反应信息

• 作为反应物：
  描述：

  4-溴邻苯二酚 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 sodium hydride 、 potassium carbonate 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1821.75h， 生成 (E)-[1-(13)C,3-(13)C]-2,4-bis(benzyloxy)-2-(3-(3',4'-bis(benzyloxy)phenyl)allyl)phenol
  参考文献：
  名称：

  Synthesis of [2-13C, 4-13C]-(2R,3S)-catechin and [2-13C, 4-13C]-(2R,3R)-epicatechin

  摘要：

  首次从标记的2-羟基-4,6-双(苄氧基)乙酰苯3和标记的3,4-双(苄氧基)苯甲醛7出发，合成了双标记的[2-¹³C,4-¹³C]-(2R,3S)-儿茶素15和[2-¹³C,4-¹³C]-(2R,3R)-表儿茶素18。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1791
• 作为产物：
  描述：

  2,2-二甲基-1,3-苯并二恶茂烷 在 硫酸 、 溴 、 乙酸酐 作用下， 生成 4-溴邻苯二酚
  参考文献：
  名称：

  Slooff, Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 995,999

  摘要：

  DOI：

文献信息

• Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica
  作者：Mylène de Léséleuc、Andrew Kukor、Shaun D. Abbott、Boulos Zacharie

  DOI：10.1002/ejoc.201901239

  日期：2019.11.30

  A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol functionalized on silica gel. This is an application for the well‐known commercial solid‐supported thiol (Silia MetS ® Thiol). The procedure is mild and amenable to scale‐up. It does not require inert atmosphere and

  开发了一种实用，有效且通用的方法，使用在硅胶上官能化的硫醇将各种芳族和脂族缩醛脱保护为相应的邻苯二酚或二醇衍生物。这是著名的商业固载硫醇（Silia MetS®Thiol）的应用。该过程是温和的，并且可以扩大规模。它不需要惰性气氛，并且观察到干净的转化。此方法适用于具有不同功能的取代1,3-苯并二恶唑和脂族缩醛。它提供了高收率的常规路线的优势，可以在环境温度下进行。
• Azabicycloalkane compounds
  申请人：——

  公开号：US20040242622A1

  公开（公告）日：2004-12-02

  This invention provides compounds of formula I: 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The compounds of this invention possess both &bgr; 2 adrenergic receptor agonist and muscarinic receptor antagonist activity. Such compounds are useful for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

  这项发明提供了式I的化合物： 其中R1、R2、R3、R4、R5、R6和R7如规范中所定义，或其药用可接受盐、溶剂或立体异构体。本发明的化合物具有β2肾上腺素受体激动剂和肌碱受体拮抗剂活性。这些化合物对治疗肺部疾病，如慢性阻塞性肺病和哮喘，是有用的。
• Pyrrolo-pyridine kinase modulators
  申请人：Arnold D. William

  公开号：US20060030583A1

  公开（公告）日：2006-02-09

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂以及利用这些新型吡咯-吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。
• Regioselective, photochemical bromination of aromatic compounds using N-bromosuccinimide
  作者：Prakash K. Chhattise、A.V. Ramaswamy、Suresh B. Waghmode

  DOI：10.1016/j.tetlet.2007.10.126

  日期：2008.1

  Regioselective nuclear bromination of aromatic compounds is investigated with N-bromosuccinimide as the brominating agent under UV irradiation to afford the corresponding brominated compounds. The reaction proceeds at ambient temperature (30 ± 2 °C) without any catalyst. In most of the reactions, regioselectively mono-brominated products are obtained in good to high yields. The conversion and selectivity

  用N-溴琥珀酰亚胺作为溴化剂，在紫外线辐射下研究了芳香族化合物的区域选择性核溴化反应，得到了相应的溴化化合物。反应在环境温度（30±2°C）下进行，没有任何催化剂。在大多数反应中，以高产率或高产率获得区域选择性单溴化产物。溴化的转化率和选择性取决于芳环上取代基的性质。
• Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors
  作者：Mariarosaria Boccellino、Maria Donniacuo、Ferdinando Bruno、Barbara Rinaldi、Lucio Quagliuolo、Marika Ambruosi、Simona Pace、Mario De Rosa、Abdurrahman Olgaç、Erden Banoglu、Nicola Alessio、Antonio Massa、Haroon Kahn、Oliver Werz、Antonio Fiorentino、Rosanna Filosa

  DOI：10.1016/j.ejmech.2019.07.033

  日期：2019.10

  Stilbenes with well-known antioxidant and antiradical properties are beneficial in different pathologies including cardiovascular diseases. The present research was performed to investigate the potential protective effect of resveratrol (1) and piceatannol (2), against hypoxia-induced oxidative stress in the H9c2 cardiomyoblast cell line, and the underlying mechanisms. Compounds 1 and 2 significantly

  具有众所周知的抗氧化和抗自由基性能的丁二烯在包括心血管疾病在内的不同病理中均有益。进行本研究以研究白藜芦醇（1）和美​​沙酮（2）对H9c2心肌细胞系中低氧诱导的氧化应激的潜在保护作用及其潜在机制。化合物1和2在无微摩尔浓度或亚微摩尔浓度下均显着抑制过氧亚硝酸盐和硫代巴比妥酸水平的释放，这种作用在皮卡季醇处理的细胞中更为明显，以浓度依赖的方式显着增加了MnSOD蛋白水平。此外，由于天然资源中苦味甘苦的苦味酚醇比母体化合物具有更高的生物活性，我们特此报告聚焦二苯乙烯化合物库的非常快速的合成和基于结构的详细设计。最后，考虑到缺氧诱导的ROS积累也随着白三烯的产生而增加了5-脂氧合酶（5-LOX）的表达和活性，我们已经揭示了对5-LOX活性至关重要的结构关键因素。在合成的类似物（3-7）中，化合物7在改善心肌细胞活力和抑制5-LOX方面最有效。总之，建模和实验研究为进一步优化二苯乙烯类似物作为炎