2-溴甲基-4-三氟甲氧基苯硼酸频那醇酯 | 957066-13-6

• 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-溴甲基-4-三氟甲氧基苯硼酸频那醇酯
• 英文名称: 2-bromomethyl-4-trifluoromethoxyphenylboronic acid pinacol ester
• 英文别名: 2-(2-(Bromomethyl)-4-(trifluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[2-(bromomethyl)-4-(trifluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 957066-13-6
• 化学式: C₁₄H₁₇BBrF₃O₃
• 分子量: 380.997
• InChiKey: CJXUOEJTOXQAMB-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2931900090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromomethyl-4-trifluoromethoxyphenylboronic acid, pinacol ester
Synonyms: 2-(2-(Bromomethyl)-4-(trifluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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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-Bromomethyl-4-trifluoromethoxyphenylboronic acid, pinacol ester
CAS number: 957066-13-6

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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: C14H17BBrF3O3
Molecular weight: 381.0

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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-mercaptopyrimidine-5-carboxylic acid (4-fluorophenyl)amide 、 2-溴甲基-4-三氟甲氧基苯硼酸频那醇酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 N-(4-fluorophenyl)-2-({[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethoxy)phenyl]methyl}sulfanyl)pyrimidine-5-carboxamide
  参考文献：
  名称：

  去势抵抗性前列腺癌的有效组合免疫疗法

  摘要：

  接受雄激素剥夺疗法治疗的晚期前列腺癌患者中有很大一部分会复发，并不断进展为致命的转移性去势抵抗性前列腺癌 (mCRPC)。使用针对细胞毒性 T 淋巴细胞相关蛋白 4 (CTLA4) 或程序性细胞死亡 1/程序性细胞死亡 1 配体 1 (PD1/PD-L1) 的抗体进行免疫检查点阻断，可在各种重要的患者亚群中产生持久的治疗反应癌症类型。然而，mCRPC 对免疫检查点阻断显示出压倒性的从头抗性，促使人们寻找克服这种抗性的靶向疗法。已知髓源性抑制细胞 (MDSCs) 在肿瘤免疫逃避中发挥重要作用。循环 MDSC 的丰度与前列腺癌患者的前列腺特异性抗原水平和转移相关。前列腺癌小鼠模型显示 MDSCs (CD11b+Gr1+) 促进肿瘤的发生和进展。这些观察结果促使我们假设 mCRPC 中强大的免疫治疗反应可能是由免疫检查点阻断剂与中和 MDSC 但保留 T 细胞功能的靶向剂的联合作用引起的。在这里，我们开发了一种新型的

  DOI：

  10.1038/nature21676
• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 4,4,5,5-四甲基-2-(2-甲基-4-(三氟甲氧基)苯基)-1,3,2-二噁硼戊环 以 乙腈 为溶剂， 反应 0.17h， 以93%的产率得到2-溴甲基-4-三氟甲氧基苯硼酸频那醇酯
  参考文献：
  名称：

  使用N-溴代琥珀酰亚胺进行化学生产的连续光溴化反应的评估

  摘要：

  使用N在苄基和苯基上进行连续光溴化反应-溴代琥珀酰亚胺作为制备规模的玻璃板反应器中的溴源。该流动反应器系统能够独立地控制光强度，波长和反应温度，因此对反应施加了卓越的控制水平。简短的合成2-溴甲基-4-三氟甲氧基苯基硼酸频哪醇酯的优化研究使用405 nm的LED（发光二极管）阵列和乙腈作为溶剂，在20°C和10分钟的停留时间下获得了最佳条件。本研究评估了这种易于操作的溴化系统在连续流玻璃板反应器内部进行化学生产的规模化潜力。结合使用膜分离器的在线连续流液-液萃取和分离系统，

  DOI：

  10.1071/ch20372

文献信息

• Pyridine- and Pyrimidinecarboxamides as CXCR2 Modulators
  申请人：Maeda Dean Y.

  公开号：US20100210593A1

  公开（公告）日：2010-08-19

  There is disclosed pyridine- and pyrimidinecarboxamide compounds useful as pharmaceutical agents, synthesis processes, and pharmaceutical compositions which include pyridine- and pyrimidinecarboxamides compounds. More specifically, there is disclosed a genus of CXCR2 inhibitor compounds that are useful for treating a variety of inflammatory and neoplastic disorders.

  披露了作为药物剂的吡啶和嘧啶羧酰胺化合物，合成过程以及包括吡啶和嘧啶羧酰胺化合物的药物组合物。更具体地，披露了一类CXCR2抑制剂化合物，可用于治疗各种炎症和肿瘤性疾病。
• THIOPYRIMIDINECARBOXAMIDES AS CXCR1/2 MODULATORS
  申请人：Syntrix Biosystems, Inc.

  公开号：US20150038461A1

  公开（公告）日：2015-02-05

  There is disclosed a pyrimidinecarboxamide compound useful as a pharmaceutical agent, synthetic processes, and pharmaceutical compositions which include the pyrimidinecarboxamide compound. More specifically, there is disclosed a CXCR1/2 inhibitor useful for treating a variety of inflammatory and neoplastic disorders.

  本发明公开了一种嘧啶羧酰胺化合物，可用作制药剂，合成过程以及包括该嘧啶羧酰胺化合物的制药组合物。更具体地，本发明公开了一种CXCR1 / 2抑制剂，可用于治疗各种炎症和肿瘤性疾病。
• ２−［５−［Ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸
  申请人：シントリックス・バイオシステムズ・インコーポレイテッドＳＹＮＴＲＩＸ ＢＩＯＳＹＳＴＥＭＳ， ＩＮＣ．

  公开号：JP2019135244A

  公开（公告）日：2019-08-15

  【課題】医薬として有用なピリミジンカルボキシアミド化合物の提供。【解決手段】式ＳＸ−６８２で示される化合物。【選択図】なし

  【问题】提供作为药物有用的嘧啶羧酰胺化合物。【解决方法】化合物如式SX-682所示。【选择图】无。
• [EN] 2- [5- [N- (4 -FLUOROPHENYL) CARBAMOYL] PYRIMIDIN- 2 - YLSULFANYLMETHYL] -4- (TRIFLUOROMET HOXY) PHENYL] BORONIC ACID<br/>[FR] ACIDE 2-[5-[N-(4-FLUOROPHÉNYL)CARBAMOYL]PYRIDIN-2-YLSULFANYLMÉTHYL]-4-(TRIFLUOROMÉTHOXY)-PHÉNYL]BORONIQUE
  申请人：SYNTRIX BIOSYSTEMS INC

  公开号：WO2015016938A1

  公开（公告）日：2015-02-05

  There is disclosed a pyrimidinecarboxamide compound useful as a pharmaceutical agent, synthetic processes, and pharmaceutical compositions which include the pyrimidinecarboxamide compound. More specifically, there is disclosed a CXCRl/2 inhibitor useful for treating a variety of inflammatory and neoplastic disorders.

  本发明公开了一种嘧啶羧酰胺类化合物，可用作药物代理，合成工艺和包括嘧啶羧酰胺类化合物的制药组合物。更具体地，本发明公开了一种CXCRl / 2抑制剂，可用于治疗各种炎症和肿瘤性疾病。
• PYRIDINECARBOXAMIDES AS CXCR2 MODULATORS
  申请人：Syntrix Biosystems, Inc.

  公开号：EP2942346B1

  公开（公告）日：2020-05-06