2-溴-4-吡啶羧酸 | 66572-56-3

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-溴-4-吡啶羧酸
• 中文别名: 2-溴异烟酸；2-溴吡啶-4-羧酸；2-溴-4-羧酸吡啶；2-溴吡啶-4-甲酸；2-溴-4-吡啶甲酸；2溴4吡啶甲酸；2-溴-4-羧基吡啶
• 英文名称: 2-bromoisonicotinic acid
• 英文别名: 2-bromopyridine-4-carboxylic acid；2-Bromisonicotinsaeure；2-bromo-4-pyridinecarboxylic acid；2-bromo-4-carboxypyridine
• CAS: 66572-56-3
• 化学式: C₆H₄BrNO₂
• mdl: MFCD01646069
• 分子量: 202.007
• InChiKey: YBTKGKVQEXAYEM-UHFFFAOYSA-N

物化性质

• 熔点：
  229-231°C
• 沸点：
  447.2±30.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933399090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  存放在密封容器中，并置于阴凉、干燥处。请确保存储位置远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromoisonicotinic acid
Synonyms: 2-Bromo-4-pyridinecarboxylic acid

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromoisonicotinic acid
CAS number: 66572-56-3

---

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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

---

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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H4BrNO2
Molecular weight: 202.0

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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 bromide.

---

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

2-溴-4-吡啶羧酸可以作为医药中间体和有机合成中间体，广泛应用于实验室研发及化工医药的生产过程中。

反应信息

• 作为反应物：
  描述：

  2-溴-4-吡啶羧酸 在 硫酸 、 potassium carbonate 作用下， 生成 ethyl 2-(dimethylamino)isonicotinate
  参考文献：
  名称：

  Synthesis of 2-[18F]-fluoroisonicotinic acid hydrazide, a potential radiotracer for tuberculosis diagnosis

  摘要：

  DOI：

  10.1002/jlcr.25804401159
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 potassium permanganate 作用下， 以 水 为溶剂， 反应 7.0h， 以35%的产率得到2-溴-4-吡啶羧酸
  参考文献：
  名称：

  吡啶-4-和5-羧酸的2-羰基肟†

  摘要：

  已经通过相应的吡啶-2-甲醛制备了一系列的吡啶-2-甲醛肟，它们都在4-或5-位被相应的羧酸的衍生物取代。

  DOI：

  10.1002/jhet.5570320248

文献信息

• Synthesis and Characterization of a Series of Bis-homoleptic Cycloruthenates with Terdentate Ligands as a Family of Panchromatic Dyes
  作者：Thomas W. Rees、JinFeng Liao、Alessandro Sinopoli、Louise Male、Giuseppe Calogero、Basile F.E. Curchod、Etienne Baranoff

  DOI：10.1021/acs.inorgchem.7b01412

  日期：2017.8.21

  A series of six homoleptic bis-cyclometalated ruthenium complexes, Ru(N^N^C)2, is reported where N^N^C is a 6-(2,4-difluoro-3-R3-phenyl)-4-R2-4′-R1-2,2′-bipyridine with R3 = −H or −CF3 and R2 and R1 = −COOEt or −CF3. An effective synthesis of the ligands and the complexes is described. The UV–visible absorption studies demonstrate that these complexes are panchromatic dyes absorbing up to 900 nm. Importantly

  报道了一系列六个均一的双环金属化钌络合物Ru（N ^ N ^ C）2，其中N ^ N ^ C是6-（2,4-二氟-3-R 3-苯基）-4- R 2 -4'-R 1 -2,2'-联吡啶，其中R 3 = -H或-CF 3且R 2和R 1 = -COOEt或-CF 3。描述了配体和配合物的有效合成。紫外可见吸收研究表明，这些络合物是吸收高达900 nm的全色染料。重要的是，吸收的开始仅取决于金属化苯基上的取代，而整个光谱的吸收强度是苯基和联吡啶部分上的取代基的函数。在电化学中观察到相同的趋势，因为氧化还原间隙仅取决于金属化苯基上的取代，而氧化和还原电势是苯基和联吡啶部分上的取代基的函数。用作染料敏化太阳能电池敏化剂的初步测试表明，染料上的锚定基团数量对器件效率有重要影响。
• [EN] CD38 INHIBITORS<br/>[FR] INHIBITEURS DE CD38
  申请人：MITOBRIDGE INC

  公开号：WO2021207186A1

  公开（公告）日：2021-10-14

  One embodiment of the invention is a compound represented by Formula I: or a pharmaceutically acceptable salt thereof. The variables in Formula I are defined herein. Compounds of Formula I are CD38 inhibitors, which can be used to treat a disease or condition in a subject that benefits from an increase in NAD+ or to treat a mitochondrial disorder in a subject.

  该发明的一个实施例是由化学式I表示的化合物：或其药用可接受的盐。化学式I中的变量在此处定义。化学式I的化合物是CD38抑制剂，可用于治疗需要增加NAD+的受试者的疾病或病况，或用于治疗受试者的线粒体疾病。
• Extended Structure–Activity Relationship and Pharmacokinetic Investigation of (4-Quinolinoyl)glycyl-2-cyanopyrrolidine Inhibitors of Fibroblast Activation Protein (FAP)
  作者：Koen Jansen、Leen Heirbaut、Robert Verkerk、Jonathan D. Cheng、Jurgen Joossens、Paul Cos、Louis Maes、Anne-Marie Lambeir、Ingrid De Meester、Koen Augustyns、Pieter Van der Veken

  DOI：10.1021/jm500031w

  日期：2014.4.10

  (2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure–activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP)

  成纤维细胞活化蛋白（FAP）是一种与二肽基肽酶IV（DPPIV）相关的丝氨酸蛋白酶。它已令人信服地与涉及细胞外基质重塑的多种疾病状态联系在一起。FAP抑制已被研究作为这些疾病中的几种的治疗选择，迄今为止，大多数注意力都集中在肿瘤学应用上。我们之前发现了N -4-喹啉基-Gly-（2 S）-cyanoPro支架可能是高效和选择性FAP抑制剂的一种可能。在本研究中，我们将详细探讨围绕该核心支架的结构与活性之间的关系。我们报告了广泛优化的化合物，这些化合物对相关的二肽基肽酶（DPPs）DPPIV，DPP9，DPPII和脯氨酰寡肽酶（PREP）表现出低纳摩尔抑制力和高选择性。发现所选化合物的log  D值，血浆稳定性和微粒体稳定性非常令人满意。选定抑制剂在小鼠体内的药代动力学评估表明，其口服生物利用度高，血浆半衰期高，并且具有体内选择性和完全抑制FAP的潜力。
• [EN] PYRAZOLE INHIBITORS OF THE TRANSFORMING GROWTH FACTOR<br/>[FR] DERIVES DE PYRAZOLE AGISSANT COMME DES INHIBITEURS DU FACTEUR DE CROISSANCE TRANSFORMANT
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004016606A1

  公开（公告）日：2004-02-26

  The invention relates to novel pyrazole derivatives of formula (I), which are inhibitors of the transforming growth factor, ('TGF')-ß signalling pathway, in particular, the phosphorylation of smad2 or smad3 by the TGF-β type I or activin-like kinase ('ALK')-5 receptor, methods for their preparation and their use in medicine, specifically in the treatment and prevention of a disease state mediated by this pathway.

  本发明涉及新型吡唑衍生物，其化学式为(I)，它们是转化生长因子('TGF')-β信号通路的抑制剂，特别是TGF-β I型或激活素样激酶('ALK')-5受体介导的smad2或smad3的磷酸化，以及这些衍生物的制备方法和在医学上的应用，特别是在治疗和预防由该通路介导的疾病状态。
• A New Flow Methodology for the Expedient Synthesis of Drug‐Like 3‐Aminoindolizines
  作者：Paul P. Lange、Andrew R. Bogdan、Keith James

  DOI：10.1002/adsc.201200316

  日期：2012.9.17

  A flow‐based synthesis of diversely functionalized indolizines and their aza‐analogues is described. These drug‐like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2‐bromopyridines and alkynes, employing a simple catalyst system together with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as base. The use of flow technology allows a straightforward

  描述了基于流量的功能多样的吲哚嗪及其氮杂类似物的合成。这些类药物杂环是通过串联的Sonogashira /环异构化序列生成的，从广泛使用的2-溴吡啶和炔烃开始，采用简单的催化剂体系以及1,8-二氮杂双环[5.4.0] undec-7-ene（DBU）作为基础。流动技术的使用允许直接，快速地获得各种新型化合物，并实现从毫克级到克级的线性放大，而不会降低收率。