3-氟-2-硝基吡啶 | 54231-35-5

• 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1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 3-氟-2-硝基吡啶
• 中文别名: 2-硝基-3-氟吡啶
• 英文名称: 3-fuoro-2-nitropyridine
• 英文别名: 3-fluoro-2-nitropyridine；2-nitro-3-fluoropyridine
• CAS: 54231-35-5
• 化学式: C₅H₃FN₂O₂
• mdl: MFCD04114127
• 分子量: 142.089
• InChiKey: IJVFHCSUEBAAOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  35°C
• 沸点：
  255.8±20.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• TSCA：
  N
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储温度为0-10°C；需保存在惰性气体中；避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluoro-2-nitropyridine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H314: Causes severe skin burns and eye damage
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
P310: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluoro-2-nitropyridine
CAS number: 54231-35-5

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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.
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.

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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: C5H3FN2O2
Molecular weight: 142.1

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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, hydrogen fluoride.

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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
UN Number: UN3261 Class: 8 Packing group: II
Proper shipping name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (3-Fluoro-2-nitropyridine)

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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

3-氟-2-硝基吡啶是一种有机中间体，可通过重氮化反应从3-氨基-2-硝基吡啶制备。具体步骤如下：

将40 g（288 mmol）3-氨基-2-硝基吡啶溶于140 mL 34%氟硼酸中，并在搅拌下滴加20 g（288 mmol）亚硝酸钠的水溶液（40 mL）。滴加过程中，保持反应温度在-8℃至-2℃之间。约半小时后，将悬浮液过滤，并用35 mL 34%氟硼酸和80 mL乙醚洗涤固体产物。随后，在室温下于高真空条件下干燥12小时，得到52 g橙棕色的氟硼酸盐固体。

接着，将上述干燥的固体加热至120℃分解。然后，剩余的油状物用80 mL 10%碳酸氢钠溶液处理，并使用二氯甲烷萃取。合并的萃取液经过硫酸钠干燥、过滤并在减压下除去溶剂，最终得到目标化合物——浅黄色固体。

反应信息

• 作为反应物：
  描述：

  3-氟-2-硝基吡啶 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 3-苯氧基吡啶-2-胺
  参考文献：
  名称：

  The Studies of the Intramolecular C-F-H-N Hydrogen Bonding Using Covalently-Linked Base Pair Models of F and A

  摘要：

  1H NMR 和 X 射线研究均表明，即使在 F 和 A 的共价连接碱基对模型中，也未观察到 C-F-H-N 分子内氢键。这些结果有力地支持了 Kool 的假设。

  DOI：

  10.1055/s-2001-18103
• 作为产物：
  描述：

  3-氨基-2-硝基吡啶 在 tetrafluoroboric acid 作用下， 以 甲苯 为溶剂， 生成 3-氟-2-硝基吡啶
  参考文献：
  名称：

  Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP

  摘要：

  杂环食品诱变剂 2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶 (PHIP) 和 2-氨基-1,6-二甲基咪唑[4,5-b] 的改进合成方法] 吡啶 (DMIP) 已被报道。该路线重点介绍了 2-卤代-1-甲基-咪唑并[4,5-b]吡啶与二苯甲酮亚胺的优化钯催化 Buchwald 交叉偶联，然后进行酸水解，生成化合物 7。使用精心设计的条件，Suzuki 交叉偶联反应作为8的最后一步，使用高效催化系统在杂环核上引入芳基和甲基。

  DOI：

  10.5012/jkcs.2013.57.3.361
• 作为试剂：
  描述：

  3-氨基-2-硝基吡啶 、 氟硼酸 、 亚硝酸异戊酯 在 乙醚 、 甲苯 、 水 、 Sodium sulfate-III 、 3-氟-2-硝基吡啶 、 silica gel 、 pet ether 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以to get the crude 3-fluoro-2-nitropyridine的产率得到3-氟-2-硝基吡啶
  参考文献：
  名称：

  Hydroxyphenyl derivatives and biological applications thereof

  摘要：

  本发明涉及公式（I）的羟基苯基衍生物；以及将其用作抗菌和/或抗寄生虫剂的用途。

  公开号：

  US09309179B2

文献信息

• [EN] SUBSTITUTED HETEROCYCLIC AZA DERIVATIVES<br/>[FR] DÉRIVÉS AZA HÉTÉROCYCLIQUES SUBSTITUÉS
  申请人：GRUENENTHAL GMBH

  公开号：WO2013013817A1

  公开（公告）日：2013-01-31

  The invention relates to heterocyclic aza derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及杂环氮杂基衍生物作为辣椒素受体配体，含有这些化合物的药物组合物，以及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• Substituted Heteroaromatic Pyrazole-Containing Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
  申请人：FRANK Robert

  公开号：US20130029962A1

  公开（公告）日：2013-01-31

  Substituted heteroaromatic pyrazole-containing carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also to a method of using these compounds for treating and/or inhibiting pain and further diseases and/or disorders.

  含有杂环吡唑基的羧酰胺和脲化合物作为辣椒素受体配体，含有这些化合物的药物组合物，以及使用这些化合物治疗和/或抑制疼痛以及进一步疾病和/或疾病的方法。
• [EN] SPIROLACTAM CGRP RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DE CGRP À BASE DE SPIROLACTAME
  申请人：MERCK SHARP & DOHME

  公开号：WO2013169567A1

  公开（公告）日：2013-11-14

  The present invention is directed to spirolactam analogues which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及螺内酰胺类似物，其为CGRP受体拮抗剂，可用于治疗或预防涉及CGRP的疾病，如偏头痛。该发明还涉及包含这些化合物的药物组合物，以及在预防或治疗涉及CGRP的这类疾病中使用这些化合物和组合物。
• [EN] SUBSTITUTED CYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS CYCLIQUES SUBSTITUÉS ET PROCÉDÉS D'UTILISATION
  申请人：XI NING

  公开号：WO2013138210A1

  公开（公告）日：2013-09-19

  The present invention provides novel substituted cyclic compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

  本发明提供了新颖的取代环化合物，药用可接受的盐及其制剂，用于调节蛋白酪氨酸激酶活性，并调节细胞活动，如增殖、分化、凋亡、迁移和侵袭。该发明还提供了包括这些化合物的药用可接受的组合物，以及在治疗哺乳动物，特别是人类的增生性疾病中使用这些组合物的方法。
• [EN] NOVEL COMPOUNDS FOR MODULATION OF ROR-GAMMA ACTIVITY<br/>[FR] NOUVEAUX COMPOSÉS POUR LA MODULATION DE L'ACTIVITÉ ROR-GAMMA
  申请人：BIOGEN IDEC INC

  公开号：WO2014028669A1

  公开（公告）日：2014-02-20

  The present invention relates to aryl sulfones and related compounds that are modulators of ROR-gamma receptors. The invention also provides pharmaceutical compositions comprising these modulators, and methods of modulating ROR-gamma receptors using them. Also provided are methods of using aryl sulfones and related compounds as modulators of ROR-gamma to treat ROR-gamma mediated diseases.

  本发明涉及芳基砜和相关化合物，它们是ROR-gamma受体的调节剂。该发明还提供包含这些调节剂的药物组合物，以及使用它们调节ROR-gamma受体的方法。还提供了使用芳基砜和相关化合物作为ROR-gamma调节剂治疗ROR-gamma介导疾病的方法。