5-溴-1,3-二氟-2-硝基苯 | 147808-42-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 5-溴-1,3-二氟-2-硝基苯
• 中文别名: 1,3-二氟-2-硝基-5-溴苯；2,6-二氟-4-溴硝基苯；3,5-二氟-4-硝基溴苯；4-溴-2,6-二氟硝基苯
• 英文名称: 5-bromo-1,3-difluoro-2-nitrobenzene
• 英文别名: 2,6-difluoro-4-bromonitrobenzene；4-bromo-2,6-difluoronitrobenzene
• CAS: 147808-42-2
• 化学式: C₆H₂BrF₂NO₂
• 分子量: 237.988
• InChiKey: ABAGKHWCTWMUDH-UHFFFAOYSA-N

物化性质

• 沸点：
  266 °C
• 密度：
  1.890
• 闪点：
  114 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2904909090
• 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、密封、干燥保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-1,3-difluoro-2-nitrobenzene
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: 5-Bromo-1,3-difluoro-2-nitrobenzene
CAS number: 147808-42-2

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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: C6H2BrF2NO2
Molecular weight: 238.0

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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, nitrogen oxides, 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

应用

5-溴-1,3-二氟-2-硝基苯主要用于有机合成和医药化学领域，常作为药物分子和生物活性分子合成的中间体。其溴原子在钯催化下可以与芳基硼酸或硼酸酯进行Suzuki偶联反应。

制备

将4-溴-2,6-二氟苯胺（60.0 g，0.274 mol）溶解于乙酸（600 mL）中，随后加入过硼酸钠（89 g，0.548 mol）的乙酸溶液（800 mL）。反应混合物在65-70℃下搅拌反应2小时后，转移至65℃继续搅拌3小时。接下来，在4小时内逐渐添加额外的过硼酸钠（89 g，0.548 mol），并在同一温度下再搅拌14小时。

反应结束后，将冷反应混合物加入冰水中，用乙酸乙酯-正己烷（1:1）萃取产物，并合并提取液。有机层依次用水、10% 碳酸钾溶液和10% 硫酸氢钾溶液洗涤，然后通过无水MgSO4干燥。过滤混合物并浓缩滤液，最后在乙酸乙酯-正己烷混合溶液中重结晶提纯残余物，即可获得产物5-溴-1,3-二氟-2-硝基苯。

反应信息

• 作为反应物：
  描述：

  5-溴-1,3-二氟-2-硝基苯 在 吡啶 、 甲醇 、 potassium tert-butylate 、 sodium methylate 、 potassium carbonate 、 氯化铵 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.83h， 生成 5-[2-(benzyloxy)-4-bromo-6-fluorophenyl]-1λ⁶,2,5-thiadiazolidine-1,1,3-trione
  参考文献：
  名称：

  [EN] PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF
  [FR] INHIBITEURS DE PROTÉINE TYROSINE PHOSPHATASE ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本文提供了用于抑制蛋白酪氨酸磷酸酶的化合物、组合物和方法，例如蛋白酪氨酸磷酸酶非受体型2（PTPN2）和/或蛋白酪氨酸磷酸酶非受体型1（PTPN1），以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病、紊乱和状况的方法，例如癌症或代谢性疾病。

  公开号：

  WO2020186199A1
• 作为产物：
  描述：

  4-溴-2,6-二氟苯胺 在 sodium peroxoborate tetrahydrate 作用下， 以 溶剂黄146 为溶剂， 以66%的产率得到5-溴-1,3-二氟-2-硝基苯
  参考文献：
  名称：

  具有强力抗菌活性的新型DNA促旋酶和拓扑异构酶IV双靶标苯并咪唑尿素抑制剂：通过明智地使用结构指导的设计和结构与活性之间的关系，实现智能设计和进化。

  摘要：

  为了克服影响所有目前使用的抗生素种类的细菌耐药性问题，发现具有新颖作用机制的新型抗菌剂是必要的。细菌DNA促旋酶和拓扑异构酶IV是氟喹诺酮类抗生素的特征明确的临床验证靶标，它们通过抑制催化亚基发挥其抗菌活性。通过与它们的ATP位点相互作用来抑制这些靶标在临床上不太成功。提出了一种新型的低分子量，与ATP位点结合的回旋酶和拓扑异构酶IV合成抑制剂的发现和表征。苯并咪唑脲是两种酶的双重靶向抑制剂，并且对引起医院和社区获得性感染的各种相关病原体具有有效的抗菌活性。描述了通过使用结构指导的设计，建模和结构-活性关系来发现和优化这种新型抗菌剂。提供了在两种啮齿动物感染模型中通过口服和静脉内给药的酶抑制，抗菌活性和体内功效的数据。

  DOI：

  10.1021/jm800318d

文献信息

• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2017012647A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds according to Formula (I), wherein R1, R3, R4, R5, L1, and Cy are as defined herein. The present invention also provides compounds, methods for the production of said compounds of the invention, pharmaceutical compositions comprising the same and their use in allergic or inflammatory conditions, autoimmune diseases, proliferative diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformations, and/or diseases associated with hypersecretion of IL6 and/or interferons. The present invention also methods for the prevention and/or treatment of the aforementioned diseases by administering a compound of the invention.

  本发明公开了根据式（I）的化合物，其中R1、R3、R4、R5、L1和Cy如本文所定义。本发明还提供了该发明的化合物、制备该化合物的方法、包括相同化合物的药物组合物以及它们在过敏或炎症症状、自身免疫疾病、增殖性疾病、移植排斥、涉及软骨周转障碍的疾病、先天软骨畸形和/或与IL6和/或干扰素过度分泌相关的疾病中的使用。本发明还提供了通过给予该发明的化合物来预防和/或治疗上述疾病的方法。
• Design and Synthesis of a Highly Selective and <i>In Vivo</i>-Capable Inhibitor of the Second Bromodomain of the Bromodomain and Extra Terminal Domain Family of Proteins
  作者：Alex Preston、Stephen Atkinson、Paul Bamborough、Chun-wa Chung、Peter D. Craggs、Laurie Gordon、Paola Grandi、James R. J. Gray、Emma J. Jones、Matthew Lindon、Anne-Marie Michon、Darren J. Mitchell、Rab K. Prinjha、Francesco Rianjongdee、Inmaculada Rioja、Jonathan Seal、Simon Taylor、Ian Wall、Robert J. Watson、James Woolven、Emmanuel H Demont

  DOI：10.1021/acs.jmedchem.0c00605

  日期：2020.9.10

  better understand the contribution of each domain to their efficacy and improve their safety profile, selective inhibitors are required. This article discloses the profile of GSK046, also known as iBET-BD2, a highly selective inhibitor of the second bromodomains of the BET proteins that has undergone extensive pre-clinical in vitro and in vivo characterization.

  泛溴结构域和额外末端结构域（BET）抑制剂与BET蛋白质家族的八个溴结构域等价相互作用，并且在炎症或肿瘤学中的许多体外表型测定和体内临床前模型中显示出深远的功效。这些抑制剂中的许多已经发展到临床上，据报道药理学驱动的不良事件。为了更好地理解每个域对其功效的贡献并改善其安全性，需要选择性抑制剂。本文公开了GSK046（也称为iBET-BD2）的概况，它是BET蛋白第二个溴结构域的高度选择性抑制剂，已经在体外和体内进行了广泛的临床前研究 表征。
• [EN] IMIDAZO[1,2-A]PYRAZINE MODULATORS OF THE ADENOSINE A2A RECEPTOR<br/>[FR] MODULATEURS DE 5,6-BICYCLO-IMIDAZO[1,2-A]PYRAZINE DU RÉCEPTEUR A2A DE L'ADÉNOSINE
  申请人：SELVITA S A

  公开号：WO2019002606A1

  公开（公告）日：2019-01-03

  The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers, isotopologues,or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer, isotopologues,or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.

  本发明涉及式(I)的化合物及其盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物。本发明进一步涉及将该化合物或盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物用作药物的用途，以及包含该化合物的药物组合物。
• Gyrase inhibitors and uses thereof
  申请人：——

  公开号：US20040235886A1

  公开（公告）日：2004-11-25

  The present invention relates to compounds which inhibit bacterial gyrase and/or Topo IV and pharmaceutically acceptable compositions comprising said compounds. These compounds, and compositions thereof, are useful in treating bacterial infection. Accordingly, the present invention also relates to methods for treating bacterial infections in mammals.

  本发明涉及抑制细菌旋转酶和/或Topo IV的化合物以及包含该类化合物的药学上可接受的组合物。这些化合物及其组合物在治疗细菌感染方面具有用途。因此，本发明还涉及治疗哺乳动物细菌感染的方法。
• [EN] QUINOXALINONE COMPOUNDS, COMPOSITIONS, METHODS, AND KITS FOR INCREASING GENOME EDITING EFFICIENCY<br/>[FR] COMPOSÉS DE QUINOXALINONE, COMPOSITIONS, PROCÉDÉS ET KITS POUR AUGMENTER L'EFFICACITÉ D'ÉDITION DU GÉNOME
  申请人：VERTEX PHARMA

  公开号：WO2019143677A1

  公开（公告）日：2019-07-25

  Compounds, methods of editing a target genomic region(s), methods of repairing of a DNA break via a HDR pathway, methods of inhibiting or suppressing repair of a DNA break via a NHEJ pathway, and methods of modifying expression of a gene(s) or protein(s) comprise administering to one or more cells that include one or more target genomic regions, a genome editing system and a DNA protein-kinase (DNA-PK) inhibitor disclosed herein. Kits and compositions for editing a target gene comprise a genome editing system and a DNA-PK inhibitor disclosed herein.

  化合物，编辑目标基因组区域的方法，通过HDR途径修复DNA断裂的方法，通过NHEJ途径抑制或抑制修复DNA断裂的方法，以及修改基因或蛋白表达的方法包括向包括一个或多个目标基因组区域的一个或多个细胞施用本文披露的基因组编辑系统和DNA蛋白激酶（DNA-PK）抑制剂。用于编辑目标基因的试剂盒和组合物包括本文披露的基因组编辑系统和DNA-PK抑制剂。