5-溴-2-三氟甲氧基苯甲醛 | 923281-52-1

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-溴-2-三氟甲氧基苯甲醛
• 中文别名: 5-溴-2-(三氟甲氧基)苯甲醛
• 英文名称: 5-bromo-2-(trifluoromethoxy)benzaldehyde
• CAS: 923281-52-1
• 化学式: C₈H₄BrF₃O₂
• 分子量: 269.018
• InChiKey: IBEWLWBZTHFCPI-UHFFFAOYSA-N

物化性质

• 沸点：
  245.1±35.0 °C(Predicted)
• 密度：
  1.706±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

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：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Bromo-2-(trifluoromethoxy)benzaldehyde
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P362: Take off contaminated clothing and wash before reuse
P321: Specific treatment (see on this label)
P332+P313: If skin irritation occurs: Get medical advice/attention
P337+P313: If eye irritation persists get medical advice/attention

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Section 3. Composition/information on ingredients.
5-Bromo-2-(trifluoromethoxy)benzaldehyde
Ingredient name:
CAS number: 923281-52-1

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
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

制备方法与用途

在0℃下，向二异丙胺（3.5 mL）的THF（50 mL）溶液中加入1.6 mol/L正丁基锂的己烷溶液（15 mL）。将反应混合物冷却至-78℃后，逐步加入1-溴-4-（三氟甲氧基）苯（6.0 g），搅拌2小时。然后向反应混合物中添加吗啉-4-甲醛（8.6 g），并在减压下浓缩至干。将水加入残余物中，并用乙酸乙酯萃取。有机层依次用饱和碳酸氢钠水溶液和盐水洗涤，再用无水硫酸镁干燥并浓缩。通过硅胶柱色谱法（溶剂梯度：0→30% 乙酸乙酯/己烷）纯化残余物，最终得到5-溴-2-三氟甲氧基苯甲醛（5.04 g，收率75%），为无色油状物。

反应信息

• 作为反应物：
  描述：

  5-溴-2-三氟甲氧基苯甲醛 在 盐酸羟胺 、 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 18.0h， 生成 5-(methoxymethyl)-2-(trifluoromethoxy)benzaldehyde oxime
  参考文献：
  名称：

  [EN] N-(ARYLALKYL)-N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS
  [FR] COMPOSÉS DE N-(ARYLALKYLE)-N'-PYRAZOLYLE-URÉE, DE THIOURÉE, DE GUANIDINE ET DE CYANOGUANIDINE EN TANT QU'INHIBITEURS DE LA KINASE TRKA

  摘要：

  公式I的化合物或立体异构体、互变异构体、或药用可接受的盐、溶剂化物或前药，其中环A、环C、X、Ra、Rb、Rc、Rd和n如本文所述定义，是TrkA激酶的抑制剂，可用于治疗可以用TrkA激酶抑制剂治疗的疾病，如疼痛、癌症、炎症/炎症性疾病、神经退行性疾病、某些传染病、舍格伦综合症、子宫内膜异位症、糖尿病周围神经病变、前列腺炎或骨盆疼痛综合征。

  公开号：

  WO2014078331A1
• 作为产物：
  描述：

  N-甲酰吗啉 、 对溴三氟甲氧基苯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以75%的产率得到5-溴-2-三氟甲氧基苯甲醛
  参考文献：
  名称：

  WO2007/15588

  摘要：

  公开号：

文献信息

• [EN] CYCLOPENTADIONE DERIVED HERBICIDES<br/>[FR] HERBICIDES DÉRIVÉS DE LA CYCLOPENTADIONE
  申请人：SYNGENTA LTD

  公开号：WO2010102848A1

  公开（公告）日：2010-09-16

  Compounds of Formula (I), wherein the substituents are as defined in claim 1, are suitable for use as herbicides.

  式(I)的化合物，其中取代基如权利要求书1中定义的那样，适用于用作除草剂。
• [EN] ANTIDIABETIC SPIROCHROMAN COMPOUNDS<br/>[FR] COMPOSÉS DE SPIROCHROMANE ANTIDIABÉTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2018118670A1

  公开（公告）日：2018-06-28

  Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

  结构式（I）的新化合物及其药用盐是G蛋白偶联受体40（GPR40）的激动剂，可能在治疗、预防和抑制由G蛋白偶联受体40介导的疾病方面有用。本发明的化合物可能在治疗2型糖尿病以及与该疾病常相关的病症，包括肥胖和脂质紊乱，如混合型或糖尿病性脂质代谢异常、高脂血症、高胆固醇血症和高甘油三酯血症方面有用。
• [EN] NOVEL HERBICIDES<br/>[FR] NOUVEAUX HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2010081755A1

  公开（公告）日：2010-07-22

  Compounds of formula (I), wherein the substituents are as defined in claim 1, are suitable for use as herbicides.

  式（I）的化合物，其中取代基如权利要求1所定义的那样，适用作为除草剂。
• ピペリジニルピラゾロピリジン誘導体の結晶
  申请人：第一三共株式会社

  公开号：JP2015113323A

  公开（公告）日：2015-06-22

  【課題】レシチンコレステロールアセチルトランスフェラーゼ（ＬＣＡＴ）活性化作用を有し、動脈硬化症、動脈硬化性心疾患、冠状動脈性心疾患（心不全、心筋梗塞、狭心症、心虚血、心血管障害及び血管形成性再狭窄を含む）、脳血管疾患（脳卒中及び脳梗塞を含む）、末梢血管疾患（糖尿病血管合併症を含む）、脂質異常症、低ＨＤＬコレステロール血症、若しくは、腎疾患の治療剤又は予防剤、特に、抗動脈硬化剤の有効成分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の結晶。[Ｒは、置換されてよいアリール基、又は、置換されてよいヘテロアリール基。］【選択図】なし

  具有LECITHIN CHOLESTEROL ACYLTRANSFERASE（LCAT）活化作用的化合物，用作动脉硬化症、动脉硬化性心脏病、冠状动脉性心脏病（心力衰竭、心肌梗塞、心绞痛、心脏缺血、心血管障碍和血管形成性再狭窄等）、脑血管疾病（中风和脑梗塞等）、外周血管疾病（糖尿病血管并发症等）、脂质异常症、低HDL胆固醇血症、或肾脏疾病的治疗剂或预防剂，特别是作为抗动脉硬化剂的有效成分的有用化合物的提供。 解决方案：由通式（I）表示的化合物或其药理上可接受的盐的晶体。【其中，R可以是可取代的芳基，或者是可取代的杂环芳基。】【图像未包含】
• Structural Simplification of a Tetrahydroquinoline-Core Peptidomimetic μ-Opioid Receptor (MOR) Agonist/δ-Opioid Receptor (DOR) Antagonist Produces Improved Metabolic Stability
  作者：Sean P. Henry、Thomas J. Fernandez、Jessica P. Anand、Nicholas W. Griggs、John R. Traynor、Henry I. Mosberg

  DOI：10.1021/acs.jmedchem.9b00219

  日期：2019.4.25

  these analogues exhibit poor metabolic stability in mouse liver microsomes, likely due to the central tetrahydroquinoline scaffold in this series. As such, a structure-activity relationship (SAR) campaign was pursued to improve their metabolic stability. This resulted in a shift from our original bicyclic tetrahydroquinoline core to a monocyclic benzylic-core system. By eliminating one of the rings in

  我们先前已经报道了一系列的μ阿片受体激动剂/δ阿片受体拮抗剂配体，可作为潜在的非成瘾阿片类镇痛药。这些配体已显示在体​​内具有活性，在小鼠的条件性位置偏爱试验中未表现出戒断综合征或奖赏行为，并且不产生依赖性。尽管这些特性很有希望，但这些类似物在小鼠肝微粒体中的代谢稳定性较差，这可能是由于该系列中的中央四氢喹啉骨架所致。因此，进行了结构-活性关系（SAR）运动以改善其代谢稳定性。这导致了从我们最初的双环四氢喹啉核心向单环苄基核心系统的转变。通过消除此支架中的一个环并探索此新核心的SAR，发现了两个有希望的类似物。这些类似物（5l和5m）在MOR时具有比吗啡更好或可比的吗啡效价和功效值，保留了其DOR拮抗剂特性，并显示出代谢稳定性提高了10倍。