2,6-二甲氧基-3-硝基吡啶 | 18677-41-3

• 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1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2,6-二甲氧基-3-硝基吡啶
• 中文别名: 26二甲氧3硝基吡啶
• 英文名称: 2,6-Dimethoxy-3-nitropyridin
• 英文别名: 2,6-dimethoxy-3-nitropyridine
• CAS: 18677-41-3
• 化学式: C₇H₈N₂O₄
• mdl: MFCD00832858
• 分子量: 184.152
• InChiKey: HZVWNFPJKCNELX-UHFFFAOYSA-N

物化性质

• 熔点：
  87-90
• 沸点：
  293.2±35.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,6-Dimethoxy-3-nitropyridine
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: 2,6-Dimethoxy-3-nitropyridine
CAS number: 18677-41-3

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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: C7H8N2O4
Molecular weight: 184.1

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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.

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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

用途

2,6-二甲氧基-3-硝基吡啶是一种医药中间体，在相关文献中报道可用于制备具有噻唑并吡啶结构的MALT1抑制剂。

制备

2,6-二甲氧基-3-硝基吡啶可用于合成一种名为1-(5-氯-2,4-二甲氧基苯基)-3-(7-(1-甲氧乙基)-2-甲基噻唑并[5,4-b]吡啶-6-基)脲的化合物，该化合物是一种MALT1抑制剂。

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基-3-硝基吡啶 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以33%的产率得到3-chloro-2,6-dimethoxy-5-nitropyridine
  参考文献：
  名称：

  [EN] SUBSTITUTED THIAZOLO-PYRIDINE COMPOUNDS AS MALT1 INHIBITORS
  [FR] COMPOSÉS DE THIAZOLO-PYRIDINE SUBSTITUÉS EN TANT QU'INHIBITEURS DE MALT1

  摘要：

  揭示了通式（I）中R1-R3的化合物，其中R1-R3的定义如本文所述，用作MALT1抑制剂治疗自身免疫和炎症性疾病或紊乱。还揭示了合成这些化合物的方法。还揭示了含有本发明化合物的药物组合物以及通过给予本发明化合物治疗患有自身免疫或炎症性疾病或紊乱的患者的方法，例如癌症。

  公开号：

  WO2018020474A1
• 作为产物：
  描述：

  6-溴-2-甲氧基-3-硝基吡啶 、 sodium methylate 生成 2,6-二甲氧基-3-硝基吡啶
  参考文献：
  名称：

  MARTANI A.; FRAVOLINI A.; SCHIAFFELLA F.; ORZALESI G.; SELLERI R.; VOLPAT+, BOLL. CHIM. FARM. , 1975, 114, NO 10, 590-597

  摘要：

  DOI：

文献信息

• Cobalt‐Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One‐Pot Synthesis of Aldimines and Amides
  作者：Kristina A. Gudun、Raikhan Zakarina、Medet Segizbayev、Davit Hayrapetyan、Ainur Slamova、Andrey Y. Khalimon

  DOI：10.1002/adsc.202101043

  日期：2022.2

  The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h−1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin

  使用与双[(2-二苯基膦基)苯基]醚 (dpephos) 连接的可商购且台式稳定的 Co(acac) 2与 HBPin 选择性室温硼氢化硝基化合物（TOF 高达 4615 h -1），耐受卤化物、羟基、氨基、醚、酯、内酯、酰胺和杂芳族官能团。这些反应提供了直接获得各种原位N-硼胺 RN(H)BPin的途径用醛和羧酸处理产生一系列醛亚胺和仲羧酰胺，而不需要脱水和/或偶联剂。以顺序一锅法将这些转化结合起来，可以从容易获得且廉价的硝基化合物直接和选择性地合成醛亚胺和仲羧酰胺。
• Ortho-selectivity in the nucleophilic aromatic substitution (SNAr) reactions of 3-substituted, 2,6-dichloropyridines with alkali metal alkoxides
  作者：Jeremy L. Yap、Kellie Hom、Steven Fletcher

  DOI：10.1016/j.tetlet.2011.06.007

  日期：2011.8

  basicities favour substitution of the chlorine ortho to the 3-substituent by alkali metal alkoxides. We present convincing evidence that coordination of the alkali metal counter-ion to the 3-substituent (nitro, ester, amide) is the origin of the ortho-selectivity to give a cyclic, six-membered transition state. Excellent ortho-selectivities (⩾98:2) for secondary and tertiary alkoxides were realized with

  3-取代的2,6-二氯吡啶已被广泛用于多种生物学靶标的小分子抑制剂的合成中。因此，氯的区域选择性置换是令人关注的。通过进行广泛的溶剂研究，我们发现低氢键碱性的非极性非质子溶剂有利于用碱金属醇盐将邻氯取代为3-取代基。我们提供令人信服的证据，表明碱金属抗衡离子与3-取代基（硝基，酯，酰胺）的配位是邻位选择性产生环状六元过渡态的起源。优秀的邻钠抗衡离子可实现仲和叔醇盐的选择性（⩾98：2），而反应性较高的伯醇盐则需要更硬，更路易斯的酸性锂抗衡离子。
• Reductive Arylation of Nitroarenes with Chloroarenes: Reducing Conditions Enable New Reactivity from Palladium Catalysts
  作者：Brett D. Akana-Schneider、Daniel J. Weix

  DOI：10.1021/jacs.3c04647

  日期：2023.7.26

  N-arylation proceeds via a novel association-reductive palladation sequence followed by reductive elimination to yield an intermediate 1,1,2-triarylhydrazine. Arylation of this intermediate by the same catalyst via a traditional amine arylation sequence forms a transient tetraarylhydrazine, unlocking reductive N–N bond cleavage to liberate the desired product. The resulting reaction allows for the synthesis

  钯催化的 C-N 键形成反应是现代合成有机化学的关键工具。尽管催化剂设计取得了进步，可以使用各种芳基（拟）卤化物，但必要的苯胺偶联配偶体通常是在硝基芳烃的离散还原步骤中合成的。理想的合成顺序将避免该步骤的必要性，同时保持钯催化的可靠反应性。在此，我们描述了还原条件如何实现新的化学步骤和经过充分研究的钯催化剂的反应性，从而产生新的、有用的转化：硝基芳烃与氯芳烃的还原芳基化形成二芳基胺。机理实验表明，在还原条件下，BrettPhos-钯配合物通过两种不同的机制催化典型惰性偶氮芳烃（通过硝基芳烃原位还原产生）的双N -芳基化。最初的N -芳基化通过新颖的缔合还原钯化序列进行，然后进行还原消除，产生中间体 1,1,2-三芳基肼。使用相同的催化剂，通过传统的胺芳基化序列对该中间体进行芳基化，形成瞬态四芳基肼，解锁还原性 N-N 键断裂，释放所需产物。由此产生的反应可以高产率合成带有各种具有合成价值的官能团和杂芳基核心的二芳基胺。
• SUBSTITUTED THIAZOLO-PYRIDINE COMPOUNDS AS MALT1 INHIBITORS
  申请人：Lupin Limited

  公开号：EP3490995A1

  公开（公告）日：2019-06-05
• US4529800A
  申请人：——

  公开号：US4529800A

  公开（公告）日：1985-07-16