2-氨基-5-溴-3-碘吡啶 | 381233-96-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 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-氨基-5-溴-3-碘吡啶
• 中文别名: 2-氨基-3-碘-5-溴吡啶
• 英文名称: 2-amino-3-iodo-5-bromopyridine
• 英文别名: 5-bromo-3-iodopyridin-2-amine；2-amino-5-bromo-3-iodopyridine；5-bromo-3-iodo-2-aminopyridine；5-bromo-3-iodopyridine-2-amine
• CAS: 381233-96-1
• 化学式: C₅H₄BrIN₂
• mdl: MFCD06659000
• 分子量: 298.909
• InChiKey: XPERZSKJGNUSHI-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112°C
• 沸点：
  308.2±42.0 °C(Predicted)
• 密度：
  2.426±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, LIGHT SENSITIVE
• 安全说明：
  S26,S36/37/39,S37
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933399090
• 危险品标志：
  Xn,Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保存方法：密封、阴凉、通风且干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-5-bromo-3-iodopyridine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
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

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-5-bromo-3-iodopyridine
CAS number: 381233-96-1

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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.
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: C5H4BrIN2
Molecular weight: 298.9

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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, hydrogen Iodide.

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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

2-氨基-3-碘-5-溴吡啶的应用

2-氨基-3-碘-5-溴吡啶可用于合成酪氨酸激酶抑制剂，用于治疗癌症或防止癌细胞扩散。此外，它还可用于合成CRAC抑制剂，以治疗自身免疫疾病和炎症性疾病。

2-氨基-3-碘-5-溴吡啶的制备

在100毫升圆底单口烧瓶中加入乙酸乙酯和乙醇混合溶剂（体积比为1:2）共38毫升，其中乙酸乙酯15毫升。插入温度计并启动磁力搅拌器，随后分批加入17.4克2-氨基-5-溴吡啶及39.38克N-碘代丁二酰亚胺。在25℃下持续搅拌反应18小时。通过薄层色谱（TLC）和气相色谱（GC）检测确保2-氨基-5-溴吡啶完全反应后，使用旋转蒸发仪去除溶剂以得到粗产品。再用正己烷与乙醇的混合溶剂进行重结晶，从而获得纯净产物2-氨基-3-碘-5-溴吡啶。经过干燥处理后，该化合物的收率为80.3%，纯度经GC检测达到97.2%。

核磁共振分析结果：1H NMR（CDCl₃, 400 MHz）: δ 7.98 (s, 1H)，δ 7.66 (s, 1H)，δ 4.96 (bs, 2H)。

反应信息

• 作为反应物：
  描述：

  2-氨基-5-溴-3-碘吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 MMV390048
  参考文献：
  名称：

  MMV390048 的碳 14 放射性标记和组织分布评估

  摘要：

  抗疟化合物 MMV390048 ([14 C]-11) 通过 3 步合成用碳 14 同位素标记。它以 15.5% 的放射化学总产率从碳 14 标记的甲基碘中获得，放射化学纯度 >99%。对白化病大鼠和色素沉着大鼠单次口服 [14 C]-11 后，研究了其组织分布特征。组织分布结果显示胃肠道和排泄器官的局部暴露高，但所有其他组织的暴露低。在所有时间点，有色大鼠眼中的放射性吸收高于白化大鼠眼中。在 6 小时时，色素大鼠眼中达到的最高积累量为 0.46%。然而，与研究的其他器官相比，这些水平仍然非常低。MMV390048 ([14 C]-11) 在白化大鼠和色素沉着大鼠的皮肤中几乎没有放射性。获得的结果支持进一步开发 MMV390048 作为潜在的抗疟化合物。

  DOI：

  10.1002/jlcr.3445
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 水合硫酸 、 periodic acid dihydrate 、 碘 、 溶剂黄146 作用下， 反应 7.0h， 以70%的产率得到2-氨基-5-溴-3-碘吡啶
  参考文献：
  名称：

  一系列双环HIV-1整合酶抑制剂的设计。第1部分：脚手架的选择

  摘要：

  提出了一种基于新型双环嘧啶酮核心的HIV整合酶抑制剂。评价了核心支架的九种变异，从而优化了6：6核心，从而得到了针对野生型HIV感染T细胞的EC 50为3 nM的化合物48。

  DOI：

  10.1016/j.bmcl.2010.07.079

文献信息

• [EN] ARYL-BIPYRIDINE AMINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINE ARYL-BIPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE
  申请人：PETRA PHARMA CORP

  公开号：WO2019126733A1

  公开（公告）日：2019-06-27

  The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I): wherein A, X, Y, Z, Q, R1, R2, R3, R4, R5, and n are described herein.

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，其化学式为（I）：其中A、X、Y、Z、Q、R1、R2、R3、R4、R5和n如本文所述。
• [EN] PROTEIN KINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE KINASE ET LEUR UTILISATION
  申请人：MERCK SERONO SA

  公开号：WO2009108670A1

  公开（公告）日：2009-09-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  揭示了苯并萘啶衍生物化合物及其类似物，包括含有这些化合物的药物组合物以及制备这些化合物的方法。这些化合物在治疗对激酶信号传导抑制、调节或调控敏感的疾病中很有用。
• Pyrrolo-pyridine kinase modulators
  申请人：Arnold D. William

  公开号：US20060030583A1

  公开（公告）日：2006-02-09

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂以及利用这些新型吡咯-吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。
• [EN] TETRAHYDROBENZOFURO[2,3-C]PYRIDINE AND BETA-CARBOLINE COMPOUNDS FOR THE TREATMENT, ALLEVIATION OR PREVENTION OF DISORDERS ASSOCIATED WITH TAU AGGREGATES<br/>[FR] COMPOSÉS DE TÉTRAHYDROBENZOFURO[2,3-C]PYRIDINE ET DE BÊTA-CARBOLINE POUR LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION DE TROUBLES ASSOCIÉS À DES AGRÉGATS DE PROTÉINE TAU
  申请人：AC IMMUNE SA

  公开号：WO2019233883A1

  公开（公告）日：2019-12-12

  The present invention relates to novel compounds of formula (I) that can be employed in the treatment, alleviation or prevention of a group of disorders and abnormalities associated with Tau (Tubulin associated unit) protein aggregates including, but not limited to, Neurofibrillary Tangles (NFTs), such as Alzheimer's disease (AD).

  本发明涉及一种可以用于治疗、缓解或预防与Tau（微管相关单元）蛋白聚集相关的一组疾病和异常的新化合物（I）的公式。这些疾病和异常包括但不限于神经原纤维缠结（NFTs），如阿尔茨海默病（AD）。
• Synthesis and evaluation of the anticoccidial activity of trifluoropyrido[1,2-a]pyrimidin-2-one derivatives
  作者：Laurence Silpa、Alisson Niepceron、Fabrice Laurent、Fabien Brossier、Mélanie Pénichon、Cécile Enguehard-Gueiffier、Mohamed Abarbri、Anne Silvestre、Julien Petrignet

  DOI：10.1016/j.bmcl.2015.11.018

  日期：2016.1

  of our chemical library to discover new molecules exhibiting in vitro activity against the invasion of host cells by Eimeria tenella revealed a lead compound with an IC50 of 15μM. Structure-activity relationship studies were conducted with 34 newly synthesized compounds to identify more active molecules and enhance in vitro activity against the parasite. Four compounds were more effective in inhibiting

  筛选我们的化学文库以发现表现出抗艾美尔球虫侵袭宿主细胞的体外活性的新分子，发现了一种铅化合物，IC50为15μM。使用34种新合成的化合物进行了结构-活性关系研究，以鉴定更多活性分子并增强体外抗寄生虫活性。四种化合物在体外抑制MDBK细胞入侵方面比先导化合物更有效。