2-三氟甲基-6-溴苯甲酸 | 177420-64-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 2-三氟甲基-6-溴苯甲酸
• 中文别名: 2-溴-6-三氟甲基苯甲酸
• 英文名称: 2-bromo-6-(trifluoromethyl)benzoic acid
• CAS: 177420-64-3
• 化学式: C₈H₄BrF₃O₂
• 分子量: 269.018
• InChiKey: AZERNJLIPMDNFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  272.4±40.0 °C(Predicted)
• 密度：
  1.773±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-6-(trifluoromethyl)benzoic acid
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-Bromo-6-(trifluoromethyl)benzoic acid
CAS number: 177420-64-3

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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: C8H4BrF3O2
Molecular weight: 269.0

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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 fluoride, 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

反应信息

• 作为反应物：
  描述：

  2-三氟甲基-6-溴苯甲酸 在 氯化亚砜 、 ammonium hydroxide 作用下， 反应 6.0h， 以85%的产率得到2-bromo-6-(trifluoromethyl)benzamide
  参考文献：
  名称：

  基于苯并异噻唑酮支架发现高效 SARS-CoV-2 Mpro 抑制剂

  摘要：

  COVID-19 大流行严重影响了全球经济和公共卫生。尽管疫苗开发取得了成功，但它不足以对抗包括 Delta 变体在内的更具传染性的突变株，这表明需要替代治疗策略，例如小分子化合物开发。在这项工作中，基于来自高通量不同化合物库筛选的活性化合物，设计并测试了一系列 SARS-CoV-2 主要蛋白酶 (M pro ) 抑制剂。与 PL pro相比，最有效的化合物 ( 16b-3)显示出有效的 SARS-CoV-2 M pro抑制作用，IC 50值为 116 nM 并且对 SARS-CoV-2 M pro具有选择性和 RdRp。这类新化合物可用作进一步优化抗 COVID-19 药物发现的潜在线索。

  DOI：

  10.1016/j.bmcl.2022.128526
• 作为产物：
  描述：

  二氧化碳 、 邻溴三氟甲苯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以71%的产率得到2-三氟甲基-6-溴苯甲酸
  参考文献：
  名称：

  试剂调制可选部位选择性：所述的金属化ø - ，米-和p -halobenzotrifluorides

  摘要：

  当分别用烷基锂（-75°C）和2,2,6,6-四甲基哌啶锂（-- 100°C）在四氢呋喃中。如果存在位置歧义，则可以利用它来建立可选的站点选择性。因此，丁基锂与2-氯-3-（三氟甲基）苯在氢/金属相互转化的2-位反应，而第二秒则与1-氯-3-（三氟甲基）苯反应。-丁基锂仅攻击6位。在2,2,6,6-四甲基哌啶锂存在下，1-溴-3-（三氟甲基）苯也表现出后者的区域选择性模式，仅产生2-溴-4-（三氟甲基）苯基锂。2-溴-6-（三氟甲基）苯基锂是直接不可及的，但是在-100°C下生成的2-溴-3-（三氟甲基）苯基锂在-75°C下异构化时形成的。

  DOI：

  10.1016/0040-4039(96)00415-7

文献信息

• 縮合二環式ヘテロ環誘導体
  申请人：第一三共株式会社

  公开号：JP2016141632A

  公开（公告）日：2016-08-08

  【課題】優れたレチノイン酸受容体関連オーファン受容体γｔ阻害作用を有し、乾癬等の治療薬として有用な化合物の提供。【解決手段】一般式（Ｉ）で表される化合物又はその薬理上許容される塩。［環Ａはピロール環、イミダゾール環又はピラゾール環；環Ｂは置換／非置換のベンゼン環、シクロヘキサジエン環、シクロペンテン環、シクロヘキセン環等；Ｒ１はＨ、ハロゲン原子等；Ｒ２はＨ、ハロゲン原子、Ｃ１−Ｃ６アルキル基等；式＝Ｑ−Ｔ−で表される基は式＝ＣＨ−ＣＨ＝ＣＨ−で表される基等；Ｚは式＝ＣＨ−で表される基等；式−Ｕ−Ｖ（ＣＯ２Ｈ）−Ｗ−で表される基は、式−ＣＨ＝ＣＨ−Ｃ（ＣＯ２Ｈ）＝ＣＨ−で表される基等］【選択図】なし

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无
• Palladium-Catalyzed Stereoselective Aza-Wacker–Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles
  作者：Rong-Shiow Tang、Li-Yuan Chen、Chin-Hung Lai、Ta-Hsien Chuang

  DOI：10.1021/acs.orglett.0c03552

  日期：2020.12.4

  Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically

  进行了钯催化的分子内串联环化反应，以合成致密的顺式/顺式稠合的氮杂四环结构。该过程涉及钯（II）催化的好氧aza-Wacker反应，然后是钯（0）催化的Heck反应。系统地研究了溶剂和苯的取代方式对一锅两步级联反应的影响，并提出了可能的机理。使用钯催化的aza-Wacker-Heck环化反应，也可以快速合成应变的五氢苯并[ f ]环戊基[ hi ]吲哚并嗪-6-和外消旋的γ-二十烷。
• Regioselective Halogen-Metal Exchange Reaction of 3-Substituted 1,2-Dibromo Arenes: The Synthesis of 2-Substituted 5-Bromobenzoic Acids
  作者：Karsten Menzel、Lisa Dimichele、Paul Mills、Doug Frantz、Todd Nelson、Michael Kress

  DOI：10.1055/s-2006-947362

  日期：2006.8

  Regioselective halogen-metal exchange reactions using isopropylmagnesium chloride were carried out on 3-substituted 1,2-dibromo arenes. Eleven examples are given.

  使用异丙基氯化镁对 3-取代的 1,2-二溴芳烃进行区域选择性卤素-金属交换反应。给出了十一个例子。
• Halogen – metal exchange of 3-substituted 1,2-dibromoarenes: the use of long-rangeJCH coupling constants to determine regiochemistry
  作者：Lisa DiMichele、Karsten Menzel、Paul Mills、Doug Frantz、Todd Nelson

  DOI：10.1002/mrc.1891

  日期：2006.11

  Regioselective halogen/metal exchange reactions were carried out on a series of 3‐substituted‐ 1,2‐dibromoarenes. Product mixtures were quenched with CO2 to form the corresponding benzoic acid analogs to facilitate HPLC and NMR analysis. Substitution at the 3‐position could readily be assigned on the basis of 2D HMBC long‐range correlations, while assignment at the 2‐position was not as straightforward

  区域选择性卤素/金属交换反应在一系列 3-取代-1,2-二溴芳烃上进行。产物混合物用CO 2 猝灭以形成相应的苯甲酸类似物以促进HPLC和NMR分析。根据二维 HMBC 长程相关性可以很容易地分配 3 位的替代，而 2 位的分配则不那么简单。使用从 1-D 1H 耦合 13C 实验中提取的三键 JCH 耦合常数测量对于呈现明确的区域分配是必要的。版权所有 © 2006 John Wiley & Sons, Ltd.
• Relay Propagation of Crowding: The Trifluoromethyl Group as Both an Emitter and Transmitter of Steric Pressure
  作者：Manfred Schlosser、Fabrice Cottet、Christophe Heiss、Olivier Lefebvre、Marc Marull、Eric Masson、Rosario Scopelliti

  DOI：10.1002/ejoc.200500728

  日期：2006.2

  2-Bromo-4-(trifluoromethyl)pyridine, aza-analogous to the parent model arene 3-bromobenzotrifluoride, and both the benzo-azaanalogous 2-bromo-4-(trifluoromethyl)quinoline and its regioinverted isomer 4-bromo-2-(trifluoromethyl)quinoline are again readily deprotonated at the Br- and CF3-flanked positions. However, the buttressing caused by the introduction of a methoxy group at the peri-(5-)position impedes

  而锂 2,2,6,6-四甲基哌啶 (LITMP) 摘要。仅来自 3-溴代三氟化物的 4-位的质子，当在 N,N,N',N'',N''-五甲基二亚乙基三胺和叔丁醇钾存在下使用时，相同的碱基选择性地攻击 2-位（ qFaigl mixq)。1-Bromo-3,5-双(三氟甲基)苯也在2-位发生金属化，但[2-溴-4-(三氟甲基)苯基]硅烷根本不反应，显然被C-SiR3/ C-Br 支撑作用。2-Bromo-4-(trifluoromethyl)pyridine，氮杂类似于母体模型芳烃 3-溴三氟化物，以及苯并氮杂类似的 2-bromo-4-(trifluoromethyl)quinoline 及其区域转化异构体 4-bromo-2-(三氟甲基）喹啉再次在 Br 和 CF3 侧翼位置容易去质子化。然而，在周围 (5-) 位引入甲氧基引起的支撑阻碍了溴（三氟甲基）喹啉的去质子化。与甲氧基相比，peri-Me