2,6-双(三氟甲基)溴苯 | 118527-30-3

• 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: 2,6-双(三氟甲基)溴苯
• 英文名称: 2-bromo-1,3-bis-(trifluoromethyl)-benzene
• 英文别名: 2,6-bis(trifluoromethyl)bromobenzene；1-bromo-2,6-bis(trifluoromethyl)benzene；2-Bromo-1,3-bis(trifluoromethyl)benzene
• CAS: 118527-30-3
• 化学式: C₈H₃BrF₆
• 分子量: 293.006
• InChiKey: KMISZWJLTZOROU-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52℃
• 沸点：
  159℃
• 密度：
  1.697
• 闪点：
  50℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26/36
• 海关编码：
  2903999090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,6-Bis(trifluoromethyl)bromobenzene
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: 2,6-Bis(trifluoromethyl)bromobenzene
CAS number: 118527-30-3

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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: C8H3BrF6
Molecular weight: 293

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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：

  2,6-双(三氟甲基)溴苯 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以95%的产率得到2-bromo-5-nitro-1,3-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  [EN] SALICYLANILIDE ANALOGS FOR USE IN THE TREATMENT OF CORONAVIRUS
  [FR] ANALOGUES DE SALICYLANILIDE DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DU CORONAVIRUS

  摘要：

  本文提供了一种使用水杨基苯胺类似物治疗哺乳动物冠状病毒感染的方法。此外，本文还提供了一种使用水杨基苯胺类似物与一个或多个其他对治疗SARS-CoV-2感染有用的化合物相结合来治疗哺乳动物冠状病毒感染的方法。

  公开号：

  WO2022076565A1
• 作为产物：
  描述：

  间二三氟甲苯 、 正丁基锂 以31%的产率得到
  参考文献：
  名称：

  KODAIRA, KAZUO;OKUHARA, KUNIO, BULL. CHEM. SOC. JAP., 61,(1988) N 5, 1625-1631

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-甲酰基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 sodium carbonate 、 2,6-双(三氟甲基)溴苯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以21%的产率得到二苯基-2,2-二甲醛
  参考文献：
  名称：

  利用受阻氟化芳烃在 Suzuki-Miyaura 交叉偶联反应中鉴定出令人惊讶的硼酸均偶联过程

  摘要：

  对 2-溴-1,3-双（三氟甲基）苯与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应进行了评估，并确定在脱卤过程中会形成大量硼酸均偶联产物。该过程中的均偶联产物形成可能通过罕见的质子分解/第二次金属转移事件发生，而不是通过需要 O2 参与的完善机制。研究了这种硼酸均偶联反应的范围，并显示出以缺电子芳基硼酸为主。最后，通过使用二环己基（2'，6'-二甲氧基联苯-2-基）膦（SPhos）作为配体，可以获得良好的交叉偶联产物。

  DOI：

  10.1055/s-0040-1707266

文献信息

• 7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification
  作者：Xiaoqiang Yu、Min He、Shilei Yang、Ming Bao

  DOI：10.1055/s-0040-1720887

  日期：2022.7

  Self-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

  自组装的7,10-二溴-2,3-二氰基吡啶菲烯聚集体，与Ni催化剂结合，作为一种新的有机光催化剂，用于羧酸与芳基卤化物的Caryl–Oacyl交叉偶联反应。这种可见光诱导的Caryl–Oacyl键合反应顺利进行，产率从令人满意到优异。
• Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP
  作者：Yan Zhang、Mingze Xia、Min Li、Qian Ping、Zhenbo Yuan、Xuanzhong Liu、Huimin Yin、Shuping Huang、Yijian Rao

  DOI：10.1021/acs.joc.1c01876

  日期：2021.11.5

  triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the

  能量转移在光催化中起着特殊的作用，它通过间接激发利用激发态的势能，其中光敏剂决定了反应的热力学可行性。受天然产物尾孢菌素的能量转移能力的启发，我们通过对尾孢菌素的结构修饰，开发了一种绿色高效的有机光敏剂 HiBRCP（六异丁酰还原尾孢菌素）。经过结构操作后，其三重态能量大大提高，从而显着促进烯烃从E-异构体到Z-异构体的高效几何异构化。-异构体。此外，它对能量转移介导的有机金属催化也很有效，通过从 HiBRCP 到镍配合物的有效能量转移，可以实现芳基溴化物和羧酸的交叉偶联。因此，对结构操纵与其光物理性质之间关系的研究为尾孢菌素的进一步修饰提供了指导，可应用于更有意义和更具挑战性的能量转移反应。
• Catalyst-Controlled Aliphatic C–H Oxidations with a Predictive Model for Site-Selectivity
  作者：Paul E. Gormisky、M. Christina White

  DOI：10.1021/ja407388y

  日期：2013.9.25

  Selective aliphatic C-H bond oxidations may have a profound impact on synthesis because these bonds exist across all classes of organic molecules. Central to this goal are catalysts with broad substrate scope (small-molecule-like) that predictably enhance or overturn the substrate's inherent reactivity preference for oxidation (enzyme-like). We report a simple small-molecule, non-heme iron catalyst that

  选择性脂肪族 CH 键氧化可能对合成产生深远的影响，因为这些键存在于所有类别的有机分子中。该目标的核心是具有广泛底物范围（类小分子）的催化剂，其可预见地增强或推翻底物对氧化（类酶）的固有反应偏好。我们报告了一种简单的小分子非血红素铁催化剂，它在一系列拓扑不同的底物上以制备产率实现了可预测的催化剂控制的位点选择性。催化剂反应模型定量地将底物的固有物理性质与观察到的位点选择性相关联，作为催化剂的函数。
• Synthesis, characterization and application of organorhenium(<scp>vii</scp>) trioxides in metathesis reactions and epoxidation catalysis
  作者：Florian Dyckhoff、Su Li、Robert M. Reich、Benjamin J. Hofmann、Eberhardt Herdtweck、Fritz E. Kühn

  DOI：10.1039/c8dt02326c

  日期：——

  l)phenyl]zinc 4a were prepared. The properties and structure of 1b–5 were studied by means of 1H, 13C, 19F and 17O NMR, IR, MS, TGA and elemental analysis. Due to the strong Lewis acidity of the Re(VII) centres crystal structures of complexes 1b and 2b were obtained as THF adducts 1b·THF and 2b·THF. Complexes 1b, 2b, 3b·THF and 5 have been examined as catalysts in olefin epoxidation using cis-cyclooctene

  提出了四种类型为L–ReO 3的新型有机or（VII）氧化物：[4-（三氟甲基）苯基]三氧or 1b，[4-（三氟甲氧基）苯基]三氧or 2b，[4-（三氟甲基）四氟苯基]三氧（（THF） ）3b·THF和（2,2,6,6-四甲基哌啶-1-基）三氧or 5。作为中间产物，制备了新颖的二芳基锌化合物双[4-（三氟甲氧基）苯基]锌2a和双[2，6-双（三氟甲基）苯基]锌4a。通过1 H，13 C，19 F和17研究了1b-5的性质和结构NMR，IR，MS，TGA和元素分析。由于Re（VII）中心的强路易斯酸度，得到了作为THF加合物1b·THF和2b·THF的配合物1b和2b的晶体结构。使用顺式-环辛烯作为模型底物，已经研究了配合物1b，2b，3b·THF和5作为烯烃环氧化反应的催化剂。使用1b，2b和3b·THF，并使用TBHP作为CDCl 3中的氧化剂，可以得到约80％的环氧收率和TOF>
• Preparation of Fluorine-Containing Phenylacetylenes by the Method of Introduction of the Ethynyl Group Using 1,1-Dichloro-2,2-difluoroethene
  作者：Kazuo Kodaira、Kunio Okuhara

  DOI：10.1246/bcsj.61.1625

  日期：1988.5

  Phenylacetylenes (ArC≡CH) having fluoro- or trifluoromethyl substituents (o-, m-, p-F; o-, m-, p-CF3; 2,4-, 2,5-, 2,6-, 3,5-(CF3)2) have been prepared from bromobenzenes (ArBr) and benzenes (ArH) using 1,1-dichloro-2,2-difluoroethene (1) by a two-step route: ArLi or ArMgBr→ArCF=CCl2→ArC≡CLi. Upon careful treatment at −70 °C with 1, o-fluorophenyllithium gave o-FC6H4CF=CCl2 in good yield, together with benzyne-derived products, such as o-(o-FC6H4)C6H4CF=CCl2. Lithiation of m-bis(trifluoromethyl)benzene at 0 °C for 9 h (24 h) followed by treatment with bromine gave 1-bromo-2,4-, 2,6-, and 3,5-bis(trifluoromethyl)benzene in 35 (38), 31 (36), and 8% (6%) yield, respectively.

  具有氟或三氟甲基取代基的苯乙炔（ArC≡CH）（邻、间、对位氟；邻、间、对位CF3；2,4-、2,5-、2,6-、3,5-双(CF3)2）已通过溴苯（ArBr）和苯（ArH）与1,1-二氯-2,2-二氟乙烯（1）的两步路线制备得到：ArLi或ArMgBr→ArCF=CCl2→ArC≡CLi。在-70°C下仔细处理时，邻氟苯基锂以良好产率生成邻FC6H4CF=CCl2，同时伴随苯炔衍生的产物，如邻(邻FC6H4)C6H4CF=CCl2。在0°C下对间双(三氟甲基)苯进行9小时（24小时）的锂化，随后用溴处理，分别以35（38）%、31（36）%和8（6）%的产率得到1-溴-2,4-、2,6-和3,5-双(三氟甲基)苯。