2,6-二溴-4-氟苯酚 | 344-20-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯酚系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,6-二溴-4-氟苯酚
• 英文名称: 2,6-dibromo-4-fluorophenol
• CAS: 344-20-7
• 化学式: C₆H₃Br₂FO
• 分子量: 269.896
• InChiKey: RRAZCUUOWIDAJS-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57°C
• 沸点：
  219.5±35.0 °C(Predicted)
• 密度：
  2.168±0.06 g/cm3(Predicted)
• 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：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36,S36/37
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  | 2～8℃ |

SDS

2,6-Dibromo-4-fluorophenol Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2,6-Dibromo-4-fluorophenol

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Category 4
Acute toxicity (Dermal)
Acute toxicity (Inhalation) Category 4
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Harmful if swallowed, in contact with skin or if inhaled
Hazard statements
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Avoid breathing dust/fume/gas/mist/vapours/spray.
[Prevention]
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Call a POISON CENTER or doctor/physician if you feel unwell.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
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.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
2,6-Dibromo-4-fluorophenol

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Section 2. HAZARDS IDENTIFICATION
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2,6-Dibromo-4-fluorophenol
>98.0%(GC)(T)
Percent:
CAS Number: 344-20-7
Chemical Formula: C6H3Br2FO

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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.
Call a POISON CENTER or doctor/physician if you feel unwell.
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.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
from the chemical:
Precautions for firefighters: 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
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
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.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Comply with laws.
Packaging material:
2,6-Dibromo-4-fluorophenol

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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.
Protective gloves.
Hand protection:
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
Very pale yellow - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:56°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
No data available
[Water]
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride, 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:
No data available
IARC =
NTP = No data available
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):
Mobility in soil
2,6-Dibromo-4-fluorophenol

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Section 12. ECOLOGICAL INFORMATION
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
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

性状

白色至淡黄色晶体粉末。

用途

2,6-二溴-4-氟苯酚是制备α-氨基酸衍生物和抗痉挛药物的重要中间体。卤代苯酚类化合物是一种重要的有机合成及医药中间体，广泛应用于医药、农药、塑料及橡胶的添加剂、消毒剂及防腐剂等精细化学品中。间卤苯酚类化合物是合成非吗啡类强效镇痛药盐酸曲马多、三芳基甲烷噻吩类抗结核病药以及4-芳基哌啶类抗瘙痒药的重要原料。2,4-二溴苯酚(DBP)是一种重要的有机化工原料，广泛用于环氧树脂、酚醛树脂、聚氨酯等的反应型阻燃剂和合成其他化工原料的中间体。

制备

目前，2,6-二溴-4-氟苯酚的合成方法主要是以4-氟苯酚为原料，经溴代反应得到目标化合物。或以3,5-二溴-1-氟苯为起始物料，通过硼酸化和氧化两步反应得到目标化合物2,6-二溴-4-氟苯酚。其合成反应式如图所示。

2,6-二溴-1-氟苯硼酸的制备

在250 mL三口瓶中加入2,2,6,6-四甲基哌啶(10.0 g，70.8 mmol)和160 mL干燥四氢呋喃，在N₂保护下，降温至-78℃。缓慢滴加正丁基锂(21.2 mL，53.0 mmol)，滴完后搅拌30 min，再缓慢滴加3,5-二溴-1-氟苯(8.3 g，35.2 mmol)，滴完后搅拌1 h，继续滴加硼酸三异丙酯(10.0 g，53.0 mmol)。滴完后搅拌2 h反应完毕。将反应液缓慢倒入冰水中，用乙酸乙酯萃取(50 mL×3)提杂，水相用1 mol·L⁻¹盐酸调pH=3～4，析出固体，抽滤，干燥，用10 mL正己烷浸泡打浆，抽滤，干燥，得5.8 g 2,6-二溴-1-氟苯硼酸。

2,6-二溴-4-氟苯酚的制备

在250 mL单口瓶中加入40 g水和氢氧化钾(1.2 g，21.4 mmol)，完全溶解后，加入2,6-二溴-1-氟苯硼酸(3 g，10.7 mmol)，缓慢滴加30%过氧化氢水溶液(6.07 g，53.5 mmol)。滴完后继续搅拌10 min，反应完毕，用1 mol·L⁻¹的盐酸调至pH=5～6，用乙酸乙酯萃取(80 mL×2)，合并有机相，用无水硫酸钠干燥，蒸干得淡黄色固体粗品。用5 mL正己烷浸泡打浆，抽滤，干燥，得2.6 g 2,6-二溴-4-氟苯酚。

反应信息

• 作为反应物：
  描述：

  2,6-二溴-4-氟苯酚 在 硝酸 作用下， 生成 2,6-二溴对苯醌
  参考文献：
  名称：

  CXXXVI.—发烟硝酸对4-卤代-2：6-二溴苯酚和-茴香醚的作用。氟衍生物的异常行为

  摘要：

  DOI：

  10.1039/jr9300001085
• 作为产物：
  描述：

  4-氟苯酚 在 dibromamine-T 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以78%的产率得到2,6-二溴-4-氟苯酚
  参考文献：
  名称：

  在没有任何催化剂的情况下使用 TsNBr2 快速和完全溴化芳族化合物

  摘要：

  摘要 N,N-二溴对甲苯磺酰胺(TsNBr2)是一种用于芳香族化合物溴化的新型试剂。反应速度极快，在环境温度下瞬间完成，只生成相应的多溴化产物。该程序适用于各种苯酚、苯甲醚和苯胺，以优异的收率得到相应的多溴化化合物作为单一产品。图形概要

  DOI：

  10.1080/00397911.2014.956367

文献信息

• Rhodium-Catalyzed Carbonylative Coupling of Alkyl Halides with Phenols under Low CO Pressure
  作者：Han-Jun Ai、Hai Wang、Chong-Liang Li、Xiao-Feng Wu

  DOI：10.1021/acscatal.0c00933

  日期：2020.5.1

  A rhodium-catalyzed carbonylative transformation of alkyl halides under low pressure of CO has been developed. This robust catalyst system allows using phenols as the carbonylative coupling partner and, meanwhile, exhibits high functional group tolerance and good chemoselectivity. Substrates even with a large steric hindrance group or multiple reaction sites can be selectively converted into the desired

  已经开发了在CO的低压下铑催化烷基卤的羰基化转化。这种强大的催化剂体系允许使用酚类作为羰基偶合伴侣，同时具有较高的官能团耐受性和良好的化学选择性。甚至具有大的位阻基团或多个反应位点的底物也可以以良好或优异的产率选择性地转化为所需产物。进行了克级实验，并交付了几乎定量的产品。还进行了对照实验，并提出了可能的反应机理。
• [EN] COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GALENEA CORP

  公开号：WO2011019738A1

  公开（公告）日：2011-02-17

  Indole compounds are disclosed. Also disclosed are methods for using the compounds to treat human and animal disease, pharmaceutical compositions of the compounds, and kits including the compounds.

  吲哚化合物已被披露。还披露了使用这些化合物治疗人类和动物疾病的方法，这些化合物的药物组合物，以及包含这些化合物的试剂盒。
• UBIQUITIN-SPECIFIC-PROCESSING PROTEASE 7 (USP7) MODULATORS AND USES THEREOF
  申请人：FLX Bio, Inc.

  公开号：US20190142834A1

  公开（公告）日：2019-05-16

  Disclosed herein, inter alia, compounds and methods of use thereof for the modulation of USP7 activity.

  本公开内容包括，但不限于，化合物及其使用方法，用于调节USP7活性。
• Expedient, High-Yielding Synthesis of Silyl-Substituted Salen Ligands
  作者：Avinash N. Thadani、Yong Huang、Viresh H. Rawal

  DOI：10.1021/ol0713436

  日期：2007.9.1

  enantioselective catalysts. The salicylaldehyde precursors are synthesized from the silyl ethers of 2,6-dibromophenols via a one-pot double lithium halogen exchanges, to induce an intramolecular retro-Brook rearrangement and allow introduction of the aldehyde group. Condensation of the salicylaldehyde products with a chiral diamine affords the silyl-substituted salen ligands in high yields. The use of other

  描述了用于制备对映选择性催化剂的甲硅烷基取代的塞伦配体的有效合成。水杨醛前体是由2，6-二溴苯酚的甲硅烷基醚通过一锅双卤化锂锂交换合成的，以诱导分子内逆布鲁克重排并允许引入醛基。水杨醛产物与手性二胺的缩合以高收率提供了甲硅烷基取代的塞伦配体。使用其他亲电试剂可轻松获得甲硅烷基取代的酚酯，酮和硼酸。
• Palladium‐Catalyzed Perfluoroalkylative Carbonylation of Unactivated Alkenes: Access to β‐Perfluoroalkyl Esters
  作者：Youcan Zhang、Hui‐Qing Geng、Xiao‐Feng Wu

  DOI：10.1002/anie.202111206

  日期：2021.11.2

  An efficient and convenient palladium-catalyzed perfluoroalkylative carbonylation of unactivated alkenes has been developed. More than 100 examples of β-perfluoroalkyl esters were prepared directly from readily available substrates with good functional group tolerance and chemoselectivity.

  已开发出一种有效且方便的钯催化的未活化烯烃的全氟烷基化羰基化。100 多个 β-全氟烷基酯的例子是直接从容易获得的底物制备的，具有良好的官能团耐受性和化学选择性。

表征谱图