2-氟-5-硝基苯硼酸频哪醇酯 | 425378-68-3

• 物质功能分类: 无机化工 - 无机盐 - 硼化物、硼酸盐和过硼酸盐
• 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-氟-5-硝基苯硼酸频哪醇酯
• 中文别名: 2-氟-5-硝基苯基硼酸频那醇酯；2-氟-5-硝基苯硼酸频呐醇酯
• 英文名称: 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 425378-68-3
• 化学式: C₁₂H₁₅BFNO₄
• 分子量: 267.065
• InChiKey: FXEVKZIXXGDLFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Fluoro-5-nitrophenylboronic acid, pinacol ester
Product Name:
Synonyms: 2-(2-Fluoro-5-nitrophenyl)-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.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P302+P352: IF ON SKIN: Wash with soap and water
P321: Specific treatment (see on this label)
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Fluoro-5-nitrophenylboronic acid, pinacol ester
Ingredient name:
CAS number: 425378-68-3

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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, refrigerated.

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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: C12H15BFNO4
Molecular weight: 267.1

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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, nitrogen oxides, hydrogen fluoride.

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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

应用

2-氟-5-硝基苯硼酸频哪醇酯是一种酯类有机物，作为有机中间体，可用于进行Suzuki反应。

制备

将2-溴-1-氟-4-硝基苯（13.2g，60mmol）、4,4,4',4',5,5,5',5'-八甲基-2,2'-联(1,3,2-二噁硼戊环)（22.8g，90mmol）、[1,1'-双(二苯基膦基)二茂铁]二氯化钯（880mg，12mmol）和乙酸钾（17.6g，180mmol）溶于1,4-二氧六环（180mL），置换氮气后加热至90℃搅拌过夜。使用LC/MS检测反应完全度。

向反应液中加入水（150mL），用乙酸乙酯（200mL）萃取，有机相用饱和食盐水（150mL*2）洗涤，再用无水硫酸钠干燥后浓缩。通过硅胶制备色谱分离纯化（石油醚：乙酸乙酯=10:1），最终得到2-氟-5-硝基苯硼酸频哪醇酯（14.0g，产率87.3%）。

反应信息

• 作为反应物：
  描述：

  2-氟-5-硝基苯硼酸频哪醇酯 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 氢溴酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 29.25h， 生成 2-(5-溴-2-氟苯基)-3-氟苯甲腈
  参考文献：
  名称：

  Discovery of Imidazo[1,2-b][1,2,4]triazines as GABA_A α2/3 Subtype Selective Agonists for the Treatment of Anxiety

  摘要：

  The identification of a series of imidazo[1,2-b][1,2,4]triazines with high affinity and functional selectivity for the GABA(A) alpha 3-containing receptor subtype is described, leading to the identification of a clinical candidate, 11. Compound 11 shows good bioavailability and half-life in preclinical species, and it is a nonsedating anxiolytic in both rat and squirrel monkey behavioral models.

  DOI：

  10.1021/jm051200u
• 作为产物：
  描述：

  对氟硝基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 溴 、 potassium acetate 、 铁粉 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 生成 2-氟-5-硝基苯硼酸频哪醇酯
  参考文献：
  名称：

  一种2-氟-5-硝基苯甲醚的合成方法

  摘要：

  本发明公开了一种2‑氟‑5‑硝基苯甲醚的合成方法，包括：步骤1，利用3‑溴‑4‑氟硝基苯和联硼酸频哪醇酯发生偶联反应，生成2‑氟‑5‑硝基苯硼酸频哪醇酯；步骤2，利用2‑氟‑5‑硝基苯硼酸频哪醇酯和高碘酸钠发生氧化水解反应，生成2‑氟‑5‑硝基苯硼酸；步骤3，利用2‑氟‑5‑硝基苯硼酸和双氧水发生氧化反应，生成2‑氟‑5‑硝基苯酚；步骤4，利用2‑氟‑5‑硝基苯酚和硫酸二甲酯发生甲基化反应，得到2‑氟‑5‑硝基苯甲醚。本发明2‑氟‑5‑硝基苯甲醚的合成方法，不但提供了一种在芳香环上引入羟基的新思路，而且产品具有较高的纯度和收率；此外，各步骤属于操作常规，所用设备常规，且原料便宜易得，适合工业化扩大生产。

  公开号：

  CN116768729A

文献信息

• 一类咪唑并吡嗪类化合物及其药物组合物和用途
  申请人：中国药科大学

  公开号：CN105254635A

  公开（公告）日：2016-01-20

  咪唑并吡嗪类衍生物、其制备方法及其作为药物的用途，本发明提供式(I)所表示的化合物及其生理学可接受的盐，其中各符号如说明书中所定义。该类化合物可以结合具有bromodomain结构域的蛋白从而调节下游的信号通路，发挥特定功能，可用于治疗与bromodomain结构域蛋白相关的多种疾病。该类化合物可干扰具有bromodomain结构域的Brd4与乙酰化组蛋白的结合，进而下调癌基因和其他相关靶基因的转录，因此可以成为肿瘤的有效治疗药物。
• 吡啶类N-氧化衍生物及其制备方法和应用
  申请人：上海翰森生物医药科技有限公司

  公开号：CN110041253B

  公开（公告）日：2022-03-29

  本发明涉及吡啶类N‑氧化衍生物及其制备方法和应用。特别地，本发明涉及通式(I)所示的化合物、其制备方法及含有该化合物的药物组合物，及其作为BRD4抑制剂在治疗癌症、炎症、慢性肝病、糖尿病、心血管疾病和AIDS等相关疾病的用途，其中通式(I)中的各取代基与说明书中的定义相同。
• [EN] IMIDAZO-PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIDINE UTILISES EN TANT QUE LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2003099816A1

  公开（公告）日：2003-12-04

  A class of 8-fluoro-3-phenylimidazo[1,2-a]pyridine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group, or by a pyrrolidinonyl group, which is directly attached or bridged by an oxygen atom or by a -NH- or -OCH2- linkage, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类8-氟-3-苯基咪唑并[1,2-a]吡啶衍生物，通过苯环的间位被一个可选择取代的芳基或杂环芳基团，或者通过一个吡咯烷基团取代，该吡咯烷基团直接连接或通过氧原子或-NH-或-OCH2-键连接，作为GABAA受体的选择性配体，特别是对其α2和/或α3和/或α5亚基具有高亲和力，因此在治疗和/或预防中枢神经系统的不良状况，包括焦虑、惊厥和认知障碍方面具有益处。
• [EN] INHIBITORS OF TRANSCRIPTIONAL ENHANCED ASSOCIATE DOMAIN (TEAD) AND USES THEREOF<br/>[FR] INHIBITEURS DU DOMAINE ASSOCIÉ D'ACTIVATION TRANSCRIPTIONNEL (TEAD) ET UTILISATIONS
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2021247634A1

  公开（公告）日：2021-12-09

  Provided herein are compounds of Formula (I''), Formula (I'), Formula (I), Formula (II'), and Formula (II), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. Also provided are methods, uses, and kits involving the disclosed compounds and pharmaceutical compositions thereof for treating and/or preventing diseases (e.g., proliferative diseases (e.g., cancers), inflammatory diseases (e.g., fibrosis), autoimmune diseases (e.g., sclerosis)) in a subject. Provided are methods of inhibiting the activity of a transcription factor (e.g., TEAD, such as TEAD1, TEAD2, TEAD3, TEAD4) and/or inhibiting the transcription of a gene (e.g., a gene controlled or regulated by a transcription factor (e.g., TEAD)) in a subject.

  本文提供了式(I'')、式(I')、式(I)、式(II')和式(II)的化合物，以及这些化合物的药学上可接受的盐、溶剂化合物、水合物、多晶形态、共晶体、互变异构体、立体异构体、同位素标记衍生物和前药。还提供了涉及所述化合物及其药物组合物的治疗和/或预防疾病（如增殖性疾病（如癌症）、炎症性疾病（如纤维化）、自身免疫疾病（如硬化症））的方法、用途和试剂盒。提供了在受试者中抑制转录因子活性（如TEAD，如TEAD1、TEAD2、TEAD3、TEAD4）和/或抑制基因转录（如由转录因子（如TEAD）控制或调节的基因）的方法。
• [EN] 4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS<br/>[FR] DÉRIVÉS DE 4-PHÉNYL-N-(PHÉNYL)THIAZOL-2-AMINE ET COMPOSÉS ASSOCIÉS UTILISÉS COMME AGONISTES DU RÉCEPTEUR D'HYDROCARBURE ARYLE (AHR) POUR LE TRAITEMENT, PAR EX., DE TROUBLE LIÉS À L'ANGIOGENÈSE OU INFLAMMATOIRES
  申请人：IKENA ONCOLOGY INC

  公开号：WO2021127301A1

  公开（公告）日：2021-06-24

  4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

  4-苯基-N-(苯基)噻唑-2-胺和4-(吡啶-3-基)-N-(苯基)噻唑-2-胺衍生物以及相应的噻二唑、噻吩、噁唑、噁二唑、咪唑和三唑衍生物和相关化合物作为芳香烃受体（AHR）激动剂，用于治疗涉及血管生成的疾病，例如视网膜病变、银屑病、类风湿性关节炎、肥胖和癌症，或炎症性疾病。