2-溴-4-三氟甲基苯甲醛 | 85118-24-7

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 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-溴-4-三氟甲基苯甲醛
• 中文别名: 2-溴-4-(三氟甲基)苯甲醛
• 英文名称: 2-bromo-4-(trifluoromethyl)benzaldehyde
• CAS: 85118-24-7
• 化学式: C₈H₄BrF₃O
• 分子量: 253.018
• InChiKey: CUKSTNNYAHZPRM-UHFFFAOYSA-N

物化性质

• 沸点：
  230.0±40.0℃ (760 Torr)
• 密度：
  1.677±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  92.9±27.3℃

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Bromo-4-(trifluoromethyl)benzaldehyde
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-4-(trifluoromethyl)benzaldehyde
CAS number: 85118-24-7

---

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.
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: C8H4BrF3O
Molecular weight: 253.0

---

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

用途

2-溴-4-三氟甲基苯甲醛可用作有机合成中间体。其制备过程包括从2-溴-1-甲基-4-三氟甲基苯氧化生成2-溴-4-（三氟甲基）苯甲酸，再还原为2-溴-4-（三氟甲基）苯基]甲烷-1-醇，最终进一步氧化得到目标产物。

制备 2-溴-4-（三氟甲基）苯甲酸的制备

向装有磁力搅拌和回流冷凝器的圆底烧瓶中加入2-溴-1-甲基-4-三氟甲基苯（7.6g，32mmol），在吡啶（75mL）中的溶液中，逐步添加高锰酸四乙铵（24g，96mmol）。将反应混合物加热至70℃并搅拌30小时。待冷却至25℃后，倒入含有浓HCl（150mL）和NaHSO₃（150g）的冰浴中。混合物变成澄清的水溶液，并用EtOAc（4×200mL）萃取，合并萃取物经饱和NaCl（200mL）洗涤、Na₂SO₄干燥并过滤后真空浓缩，得到白色固体产物。MS（ESI，负离子）m/z：267（M-1）。

2-溴-4-（三氟甲基）苯基]甲烷-1-醇的制备

在N₂保护下，0°C时向装有磁力搅拌和回流冷凝器的圆底烧瓶中加入2-溴-4-（三氟甲基）苯甲酸（5.0g，24mmol），溶于四氢呋喃溶液中。随后缓慢滴加1.0M硼烷-THF络合物（72mL，72mmol）。将反应混合物加热至65℃并搅拌2小时。冷却后，通过真空除去溶剂，并将所得残余物溶于CH₂Cl₂（100mL）中。用饱和Na₂CO₃（100mL）洗涤，再用CH₂Cl₂（4×80mL）反萃取水相，并合并有机萃取物。经饱和NaCl洗涤（200mL），并使用Na₂SO₄干燥、过滤后真空浓缩，通过硅胶色谱法纯化（梯度：0-4％EtOAc的己烷溶液），得到无色油状产物。

2-溴-4--三氟甲基苯甲醛的制备

在CH₂Cl₂（100mL）中溶解2-溴-4-（三氟甲基）苯基]甲烷-1-醇（4.4g，23mmol）。加入重铬酸吡啶鎓（38.4g，102mmol），并在25℃下搅拌过夜。通过硅藻土过滤反应混合物，并用CH₂Cl₂（2×50mL）洗涤硅藻土垫。将合并的滤液真空浓缩后，通过硅胶色谱法纯化（梯度：在己烷中的0-5％EtOAc），得到无色油状的标题产物2-溴-4-三氟甲基苯甲醛（4.6g，18mmol）。

反应信息

• 作为反应物：
  描述：

  2-溴-4-三氟甲基苯甲醛 在 哌啶 、 正丁基锂 、 硫酸 、 magnesium 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 25.5h， 生成 3-(4-氟苯基)-6-(三氟甲基)茚满-1-酮
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002
• 作为产物：
  描述：

  2-溴-4-三氟甲基溴苄 生成 2-溴-4-三氟甲基苯甲醛
  参考文献：
  名称：

  Pesticidal method using 2-phenylimidazole derivatives

  摘要：

  该发明提供了一种利用公式为2-苯基咪唑衍生物的方法来控制节肢动物、植物线虫、蠕虫或原生动物害虫：其中R.sup.1代表氢、烷基（可选地由烷氧基、烷基硫醚、烷基磺醚、烷基磺酰基、氰基、羧基或烷氧羰基取代）、R.sup.2和R.sup.3分别代表氢、卤素、硝基、羧基、氰基、烷氧羰基、烷酰基，或可选地取代的烷基取代的氨基甲酰基或磺酰基，或氨基（可选地由烷基、烷氧羰基或烷酰基取代）或R、RO、RS、RSO或RSO.sub.2基团，其中R代表烷基（可选地由卤素取代），Ar代表公式的基团：其中R.sup.4和R.sup.6分别代表卤素或R、RO、RS、RSO或RSO.sub.2基团，而R.sup.5、R.sup.7和R.sup.8分别代表如R.sup.4和R.sup.6所定义的取代基，或代表氢、羟基、羧基、硝基、氰基、氨基、烷基氨基（可选地由烷基、烷氧羰基或烷酰基取代）、烷氧羰基或烷酰基或其农药可接受的盐，排除R.sup.2和R.sup.3同时代表氢原子的化合物，以及用于该方法的组合物和公式I的新化合物。

  公开号：

  US05206257A1

文献信息

• Intermolecular Hydroacylation: High Activity Rhodium Catalysts Containing Small-Bite-Angle Diphosphine Ligands
  作者：Adrian B. Chaplin、Joel F. Hooper、Andrew S. Weller、Michael C. Willis

  DOI：10.1021/ja211649a

  日期：2012.3.14

  rhodium complexes containing methylene bridged diphosphine ligands, viz. [Rh(C(6)H(5)F)(R(2)PCH(2)PR'(2))][BAr(F)(4)] (R, R' = (t)Bu or Cy; Ar(F) = C(6)H(3)-3,5-(CF(3))(2)), are shown to be practical and very efficient precatalysts for the intermolecular hydroacylation of a wide variety of unactivated alkenes and alkynes with β-S-substituted aldehydes. Intermediate acyl hydride complexes [Rh((t)Bu(2)PCH

  含有亚甲基桥联二膦配体的易于制备且可长期稳定的铑配合物，即。[Rh(C(6)H(5)F)(R(2)PCH(2)PR'(2))][BAr(F)(4)] (R, R' = (t)Bu 或 Cy ; Ar(F) = C(6)H(3)-3,5-(CF(3))(2))，被证明是一种实用且非常有效的预催化剂，可用于多种未活化烯烃的分子间加氢酰化和带有 β-S-取代醛的炔烃。中间酰基氢化物复合物 [Rh((t)Bu(2)PCH(2)P(t)Bu(2))Hκ(2)(S,C)-SMe(C(6)H(4)CO )}(L)](+)（L = 丙酮、MeCN、[NCCH(2)BF(3)](-)）和脱羰产物 [Rh((t)Bu(2)PCH(2)P( t)Bu(2))(CO)(SMePh)](+) 已在溶液中并通过 X 射线晶体学从使用 2-(甲硫基) 苯甲醛的化学计量反应中表征。还报道了与膦 2-(二苯基膦基)苯甲醛
• [EN] PYRAZOLE MAGL INHIBITORS<br/>[FR] INHIBITEURS PYRAZOLE DE MAGL
  申请人：ABIDE THERAPEUTICS INC

  公开号：WO2018217805A1

  公开（公告）日：2018-11-29

  Provided herein are pyrazole compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of monoacylglycerol lipase (MAGL). Furthermore, the subject compounds and compositions are useful for the treatment of pain.

  本文提供了吡唑化合物和包含该化合物的药物组合物。这些化合物和组合物可用作单酰基甘油酶（MAGL）的调节剂。此外，这些化合物和组合物可用于治疗疼痛。
• PIPERAZINE CARBAMATES AND METHODS OF MAKING AND USING SAME
  申请人：ABIDE THERAPEUTICS, INC.

  公开号：US20190202801A1

  公开（公告）日：2019-07-04

  Provided herein are piperazine carbamates and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of MAGL and/or ABHD6. Furthermore, the subject compounds and compositions are useful for the treatment of pain.

  本文提供了哌嗪氨基甲酸酯和包含该化合物的药物组合物。所述化合物和组合物可用作MAGL和/或ABHD6的调节剂。此外，所述化合物和组合物可用于治疗疼痛。
• NOVEL IMIDAZOLE COMPOUND AND USE THEREOF AS MELANOCORTIN RECEPTOR AGONIST
  申请人：MITSUBISHI TANABE PHARMA CORPORATION

  公开号：US20180258076A1

  公开（公告）日：2018-09-13

  The present invention relates to a novel imidazole compound or a pharmaceutically acceptable salt thereof having a melanocortin receptor agonistic activity, and medical use thereof. The present invention relates to an imidazole compound represented by general formula [I] [wherein: Ring A represents an optionally substituted aryl group or the like; R 1 represents a hydrogen atom, an optionally substituted alkyl group, or the like; R 2 represents a hydrogen atom, a halogen atom, or the like; and R 3 represents an optionally substituted alkyl group] or a pharmaceutically acceptable salt thereof.

  本发明涉及一种具有黑皮质素受体激动活性的新型咪唑化合物或其药用可接受盐，以及其医疗用途。本发明涉及由通式[I]表示的咪唑化合物 [其中：环A代表一个可选地取代的芳香族基团等；R1代表一个氢原子，一个可选地取代的烷基团等；R2代表一个氢原子，一个卤素原子等；R3代表一个可选地取代的烷基团]或其药用可接受盐。
• 医薬組成物
  申请人：田辺三菱製薬株式会社

  公开号：JP2018199673A

  公开（公告）日：2018-12-20

  【課題】 メラノコルチン受容体作動活性を有する新規イミダゾール化合物又はその薬理的に許容し得る塩を有効成分として含んでなる医薬組成物の提供。【解決手段】 一般式〔Ｉ〕〔式中、環Ａは置換されていてもよいアリール基等を表し；Ｒ１は水素原子、置換されていてもよいアルキル基等を表し；Ｒ２は水素原子、ハロゲン原子等を表し；Ｒ３は置換されていてもよいアルキル基を表す〕で示されるイミダゾール化合物、又はその薬理的に許容し得る塩を有効成分として含んでなる医薬組成物。【選択図】 なし

  【课题】提供含有作为有效成分的新的咪唑啉化合物或其药理上可接受的盐的药物组合物，该咪唑啉化合物或其药理上可接受的盐具有melanocortin受体作用活性。 【解决手段】包含以一般式〔Ｉ〕所示的咪唑啉化合物或其药理上可接受的盐作为有效成分的药物组合物；其中，环A可以表示被取代的烯丙基等；R1可以表示氢原子、被取代的烷基等；R2可以表示氢原子、卤素原子等；R3可以表示被取代的烷基。 【选择图】无