6-溴-3-甲基-3H-咪唑并[4,5-b]吡啶 | 37805-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-溴-3-甲基-3H-咪唑并[4,5-b]吡啶
• 英文名称: 6-bromo-3-methylimidazo<4,5-b>pyridine
• 英文别名: 6-bromo-3-methyl-3H-imidazolyl(4,5-b)pyridine；6-bromo-3-methyl-3H-imidazo[4,5-b]pyridine；6-bromo-3-methyl-3H-imidazo[4,5-b]pyridine；6-Brom-3-methyl-3H-imidazo<4,5-b>pyridin；6-bromo-3-methylimidazo[4,5-b]pyridine
• CAS: 37805-78-0
• 化学式: C₇H₆BrN₃
• 分子量: 212.049
• InChiKey: AERQLDMEKUZFHF-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±45.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-3-methyl-3H-imidazo[4,5-b]pyridine
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
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

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Section 3. Composition/information on ingredients.
Ingredient name: 6-Bromo-3-methyl-3H-imidazo[4,5-b]pyridine
CAS number: 37805-78-0

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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.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H6BrN3
Molecular weight: 212.0

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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.

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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：

  6-溴-3-甲基-3H-咪唑并[4,5-b]吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 盐酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 3-甲基-3H-咪唑并[4,5-b]吡啶-6-胺
  参考文献：
  名称：

  [EN] PYRIMIDINE DERIVATIVES CAPABLE OF INHIBITING ONE OR MORE KINASES
  [FR] DÉRIVÉS DE PYRIMIDINE CAPABLES D'INHIBER UNE OU PLUSIEURS KINASES

  摘要：

  本发明的第一个方面涉及式(I)的化合物，或其药学上可接受的盐或酯，式(I)如下：其中：R1为C3-8环烷基；X为O、NR7或C3-6杂环烷基；R2为芳基、杂芳基、融合或未融合的芳基-C3-6杂环烷基或融合或未融合的杂芳基-C3-6杂环烷基，每个基可选择地由来自芳基、杂芳基、C1-6烷基、C3-7环烷基和A基的一个或多个取代基取代，其中所述C1-6烷基基可选择地由来自芳基、杂芳基、R10和A基的一个或多个取代基取代，所述杂芳基可选择地由一个或多个R10基取代；以及所述C3-6杂环烷基基可选择地包含一个或多个来自氧、硫、氮和CO的基；R3为C1-6烷基，可选择地由一个或多个来自芳基、杂芳基、-NR4R5、-OR6、-NR7(CO)R6、-NR7(CO)NR4R5、-NR7SO2R6、-NR7COOR7、-CONR4R5、C3-6杂环烷基和式(a, b, c)的取代基取代；其中R4-7和A如权利要求中所定义。进一步方面涉及所述化合物在治疗各种治疗性疾病中的使用，特别是作为一个或多个激酶的抑制剂。

  公开号：

  WO2009122180A1
• 作为产物：
  描述：

  5-溴-2-氯-3-硝基吡啶 在 tin(II) chloride dihdyrate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 18.5h， 生成 6-溴-3-甲基-3H-咪唑并[4,5-b]吡啶
  参考文献：
  名称：

  [EN] METABOTROPIC GLUTAMATE RECEPTOR MODULATORS
  [FR] MODULATEURS DES RÉCEPTEURS MÉTABOTROPIQUES DU GLUTAMATE

  摘要：

  这项发明涉及杂环衍生物及其药用可接受的盐。该发明还涉及制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病很有用。

  公开号：

  WO2011015343A1

文献信息

• Solvent-Controlled, Site-Selective <i>N</i>-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-<i>d</i>]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds
  作者：Brett C. Bookser、Michael I. Weinhouse、Aaron C. Burns、Andrew N. Valiere、Lino J. Valdez、Pawel Stanczak、Jim Na、Arnold L. Rheingold、Curtis E. Moore、Brian Dyck

  DOI：10.1021/acs.joc.8b00540

  日期：2018.6.15

  coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined

  使用NaHMDS作为碱，在THF中用碘甲烷将4-甲氧基-1 H-吡唑并[3,4- d ]嘧啶（1b）烷基化，选择性地提供了N2-甲基产物4-甲氧基-2-甲基-2 H-吡唑并[3，相对于N1-甲基产物（2b），以8/1的比例存在4- d ]嘧啶（3b）。有趣的是，在DMSO中进行反应使选择性逆转，以提供4/1的N1 / N2甲基化产物比例。产品3b的晶体结构N1和N7与钠配位表明后者可能增强N2选择性。用26个杂环测试了选择性极限，结果表明，当在THF中进行反应时，N7是控制烷基化的控制元素，对于吡唑并环而言，该环对吡唑并环反应有利于N2，对咪唑和三唑并稠合的环杂环则有利于N3。使用1个H-检测脉冲场梯度受激回波（PFG-STE）NMR确定的离子反应性复合物的分子量。该数据和DFT电荷分布计算表明，紧密离子对（CIP）或紧密离子对（TIP）控制THF中的烷基化选择性，而溶剂分离的离子对（SIPs）是DMSO中的反应性物质。
• One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
  作者：Alyn T. Davies、John M. Curto、Scott W. Bagley、Michael C. Willis

  DOI：10.1039/c6sc03924c

  日期：——

  A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the

  描述了利用钯催化从芳基和杂芳基溴化物温和有效地合成磺酰氟的方法。该方法涉及使用DABSO作为SO 2源进行钯催化的芳基溴的磺化反应，然后进行原位反应。用亲电子氟源NFSI处理所得的亚磺酸盐。该序列代表了芳基溴化物磺酰化的第一种通用方法，并为先前描述的磺酰氟合成提供了实用的一锅替代品，从而可以快速使用这些生物学上重要的分子。证明了优异的官能团耐受性，并且成功地在多种活性药物成分及其前体上实现了转化。还证明了肽衍生的磺酰氟的制备。
• [EN] ALKYNYL PHOSPHINE GOLD COMPLEXES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] COMPLEXE ALCYNYLPHOSPHINE-OR POUR TRAITER LES INFECTIONS BACTÉRIENNES
  申请人：AUSPHERIX LTD

  公开号：WO2017093544A1

  公开（公告）日：2017-06-08

  A compound of formula (I) for use in the prevention or treatment of a bacterial infection.

  一种化合物，其化学式为（I），用于预防或治疗细菌感染。
• TEMPO‐Mediated Synthesis of <i>N</i> ‐(Fluoroalkyl)imidazolones via Reaction of Imidazoles with Iodofluoroacetate
  作者：Jia‐Hao Chen、Wasim Ahmed、Ming‐Hua Li、Zhao‐Dong Li、Zi‐Ning Cui、Ri‐Yuan Tang

  DOI：10.1002/adsc.201900820

  日期：2020.1.7

  report a TEMPO‐mediated oxidative copper‐catalyzed synthesis of N‐(fluoroalkyl)imidazolones via the radical addition of imidazoles with iodofluoroacetate. A possible key intermediate involving TEMPO was observed by ESI‐MS. We also found that aerobic oxidation conditions were effective for the transformation in the presence of a copper catalyst, enabling access to a number of N‐(fluoroalkyl)imidazolones

  我们报道了通过咪唑与碘氟乙酸酯的自由基加成反应，TEMPO介导的N-（氟代烷基）咪唑啉酮的氧化铜催化合成。ESI-MS观察到可能涉及TEMPO的关键中间体。我们还发现，有氧氧化条件对于在铜催化剂存在下的转化是有效的，从而能够以中等至良好的产率获得许多N-（氟代烷基）咪唑啉酮。
• Sulfite-Induced<i>N</i>-Alkylation and Thioketonization of Azoles Enable Access to Diverse Azole Thiones
  作者：Jian-Chao Deng、Jia-Hao Chen、Jun-Rong Zhang、Ting-Ting Lu、Ri-Yuan Tang

  DOI：10.1002/adsc.201801166

  日期：2018.12.21

  base‐free N‐alkylation and thioketonization of azoles. Excellent functional group tolerance and high synthetic efficiency proved particularly advantageous for the rapid assembly of a large array of pharmaceutically‐oriented azole thiones, many of which contain synthetically and biologically useful functional groups. The direct transformation of drug molecules (such as Ketoconazole, Econazole, and Fluconazole)

  唑骨架的直接修饰使得能够接近类药物分子。为此目的，开发高度兼容的反应平台仍然具有挑战性。本文中，我们报道了亚硫酸盐作为单电子转移（SET）还原剂的用途，用于活化功能化的溴代烷烃，元素硫和咪唑啉鎓，以实现无过渡金属和无碱N的转化唑的烷基化和硫酮化。事实证明，出色的官能团耐受性和高合成效率对于快速组装大量的药用定向吡咯硫酮特别有利，其中许多含合成和生物学上有用的官能团。还成功地实现了药物分子（例如酮康唑，益康唑和氟康唑）直接转化为其相应的唑硫酮的转化。在最佳条件下，与硒的反应也顺利进行。成功的克级反应证明了该方法的良好适用性。