2-溴-6-氟苯酚 | 2040-89-3

• 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-溴-6-氟苯酚
• 中文别名: 2-氟-6-溴苯酚
• 英文名称: 2-bromo-6-fluorophenol
• 英文别名: 2-fluoro-6-bromophenol
• CAS: 2040-89-3
• 化学式: C₆H₄BrFO
• 分子量: 191.0
• InChiKey: DNFDDDWPODPCHU-UHFFFAOYSA-N

物化性质

• 熔点：
  50 °C
• 沸点：
  173.0±20.0 °C(Predicted)
• 密度：
  1.764±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 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。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Bromo-6-fluorophenol
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromo-6-fluorophenol
CAS number: 2040-89-3

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C6H4BrFO
Molecular weight: 191.0

---

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

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2-溴-6-氟苯酚是有机合成中间体和医药中间体，可用于实验室研发过程及生物化工生产中。

制备 2-氟-6-溴苯酚的合成： 3-氟-4-羟基苯磺酸钠(B)的合成(步骤a和b, 磺化反应)

1. 在反应釜中加入112克(1.0摩尔)A，将温度升至约120℃。在搅拌下于30分钟内缓慢滴加80毫升(1.5摩尔)98%硫酸。
2. 滴加完毕后，在120℃下继续反应5小时。反应结束后冷却到100℃以下。
3. 向上述反应混合物中加入400毫升饱和氯化钠溶液，生成大量钠盐沉淀。完全冷却后过滤，并用10%氯化钠溶液洗涤两次，得到192.6克产物B，产率为90%。

3-氟-6-溴-4-羟基苯磺酸钠(C)的合成(步骤c, 卤化反应)

1. 反应前将所有原料和设备进行无水处理。溴素用浓硫酸洗涤两次脱水。
2. 使用250毫升三口瓶，配机械搅拌器、温度计和分液漏斗及回流冷凝管。向烧瓶中加入171.2克(0.8摩尔)B、11.2克铁粉和120毫升四氯化碳。
3. 搅拌并水浴加热到55℃，将温度控制在50-60℃之间，在4小时内滴加134.4克(0.84摩尔)溴素。加完后保温搅拌2小时。
4. 冷却后过滤，滤液用水、碱水和水依次洗涤，干燥后蒸去溶剂，得到199克产物C，产率为85%。

2-氟-6-溴苯酚(D)的合成(步骤d, 脱保护反应)

1. 在250毫升反应釜中加入146.5克(0.5摩尔)C和200毫升70%硫酸溶液。
2. 在180℃下反应5小时后冷却到室温，加入200毫升二氯甲烷萃取。洗涤萃取液、干燥并蒸去溶剂后得到油状产物D 76.4克，产率为80%。

反应信息

• 作为反应物：
  描述：

  2-溴-6-氟苯酚 在 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.66h， 生成 3-溴邻苯二酚
  参考文献：
  名称：

  带有双（μ-氧代）双铜（III）物种的2-氟酚盐的选择性正羟基加氢脱氟

  摘要：

  双（μ-氧代）双铜（III）物种[Cu III 2（μ-O）2（m-XYL MeAN）] 2+（1）促进2-氟酚盐的亲电子邻羟基化-脱氟，得到相应的儿茶酚，反应不是accomplishable用（η 2：η 2 -O 2）亚铜（II）络合物。同位素标记研究表明，进入的氧原子源自bis（μ-oxo）单元。在分子内竞争中，与其他邻位取代基（例如氯或溴）选择性发生邻羟基化-脱氟。

  DOI：

  10.1002/anie.201405060
• 作为产物：
  描述：

  2-氟苯酚 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正戊烷 为溶剂， 反应 4.5h， 生成 2-溴-6-氟苯酚
  参考文献：
  名称：

  O-芳基N-异丙基氨基甲酸酯的定向邻锂化和异碘去甲硅烷基化反应合成卤代酚

  摘要：

  报道了通过原位 N-甲硅烷基化 O-芳基 N-异丙基氨基甲酸酯的直接邻位锂化反应区域选择性合成卤代酚。该协议由 C-甲硅烷基化氨基甲酸酯的 ipso-iododesilylation 反应和碘-镁交换反应补充，这些反应由相邻的氨基甲酰基团促进。这些方法提供了一系列 o-fluoro- 的入口。o-iodo- 和 oo'-diiodophenols 以其他方式难以获得的高产率。

  DOI：

  10.1055/s-2006-926462

文献信息

• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20140221310A1

  公开（公告）日：2014-08-07

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , L and R 2 are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention.

  本发明涉及式（I）化合物，或其形式，其中环A，R1，L和R2如本文所定义，作为FLAP调节剂有用。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE AS PESTICIDES<br/>[FR] COMPOSÉS DE TÉTRAZOLINONE ET LEUR UTILISATION EN TANT QUE PESTICIDES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013162072A1

  公开（公告）日：2013-10-31

  The present invention provides a compound having an excellent efficacy for controlling pests. A tetrazolinone compound of a formula (1): [wherein R1 represents an C6-C16 aryl group, an C1-C12 alkyl group, or a C3-C12 cycloalkyl group, etc., which each optionally be substituted; R2, R3, R4 and R5 represent independently of each other a hydrogen atom, a halogen atom or an C1-C3 alkyl group, etc.; R6 represents an C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, an C2-C6 alkenyl group, an C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, etc.; R7, R8 and R9 represent independently of each other a hydrogen atom, a halogen atom, or an C1-C4 alkyl group, etc.; X represents an oxygen atom or a sulfur atom; and R10 represents an C1-C6 alkyl group, etc.] shows an excellent controlling efficacy on pests.

  本发明提供了一种具有优异杀虫效果的化合物。公式（1）的四唑酮化合物：[其中R1代表C6-C16芳基、C1-C12烷基或C3-C12环烷基等，每个都可以选择性地被取代；R2、R3、R4和R5分别独立地代表氢原子、卤素原子或C1-C3烷基等；R6代表C1-C6烷基、C3-C6环烷基、卤素原子、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基或C1-C6卤代烷氧基等；R7、R8和R9分别独立地代表氢原子、卤素原子或C1-C4烷基等；X代表氧原子或硫原子；R10代表C1-C6烷基等]在杀虫方面表现出优异的控制效果。
• [EN] MACROCYCLES AND THEIR USE<br/>[FR] MACROCYCLES ET LEUR UTILISATION
  申请人：BLOSSOMHILL THERAPEUTICS INC

  公开号：WO2022011123A1

  公开（公告）日：2022-01-13

  The present disclosure relates to macrocyclic compounds, pharmaceutical compositions containing macrocyclic compounds, and methods of using macrocyclic compounds to treat disease, such as cancer.

  本公开涉及大环化合物、含有大环化合物的药物组合物，以及利用大环化合物治疗疾病（如癌症）的方法。
• Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization
  作者：Jiarong Shi、Lianggui Li、Chunhui Shan、Zhonghong Chen、Liang Dai、Min Tan、Yu Lan、Yang Li

  DOI：10.1021/jacs.1c04389

  日期：2021.7.21

  4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C–O, C–S, and C–C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction

  苄的 1,2,4-三取代和脱芳基 1,2,4-三官能化均由带有五-2,4-二烯-1-基部分的亚砜完成。这些级联转化通过苯炔插入 S=O 键和不常见的区域特异性阴离子 [4,5]-σ 重排进行，在 C1-、C2- 上提供 C-O、C-S 和 C-C 键, 和苯环的 C4 位，分别。该研究展示了新的级联苯炔反应模式，包括远端 C-H 键功能化和脱芳构化。
• [EN] KRAS G12D INHIBITORS<br/>[FR] INHIBITEURS DE KRAS G12D
  申请人：MIRATI THERAPEUTICS INC

  公开号：WO2021041671A1

  公开（公告）日：2021-03-04

  The present invention relates to compounds that inhibit KRas G12D. In particular, the present invention relates to compounds that inhibit the activity of KRas G12D, pharmaceutical compositions comprising the compounds and methods of use therefor.

  本发明涉及抑制KRas G12D的化合物。具体地，本发明涉及抑制KRas G12D活性的化合物，包括这些化合物的药物组合物以及使用方法。