2,6-二氯-3-甲基-5-硝基吡啶 | 58596-88-6

• 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: 2,6-二氯-3-甲基-5-硝基吡啶
• 中文别名: 2,6-二氯-3-硝基-5-甲基吡啶
• 英文名称: 2,6-dichloro-3-methyl-5-nitropyridine
• 英文别名: 2,6-dichloro-3-methyl-5-nitro-pyridine；2,6-dichloro-5-methyl-3-nitro-pyridine；2,6-dichloro-5-methyl-3-nitropyridine；2,6-Dichlor-3-methyl-5-nitro-pyridin
• CAS: 58596-88-6
• 化学式: C₆H₄Cl₂N₂O₂
• 分子量: 207.016
• InChiKey: XLKDPPLSOTVMFR-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  323.5±37.0 °C(Predicted)
• 密度：
  1.537

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 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

---

Section 1. Identification of the substance
Product Name: 2,6-Dichloro-3-methyl-5-nitropyridine
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2,6-Dichloro-3-methyl-5-nitropyridine
CAS number: 58596-88-6

---

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.

---

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.

---

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.

---

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.

---

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
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H4Cl2N2O2
Molecular weight: 207.0

---

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 chloride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,6-二氯-3-甲基-5-硝基吡啶 在 氨 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 0.5h， 生成 6-(2,2-difluoroethoxy)-5-methyl-3-nitro-2-pyridinamine
  参考文献：
  名称：

  [EN] IMIDAZOPYRIDINE COMPOUND
  [FR] COMPOSÉ IMIDAZOPYRIDINE

  摘要：

  由以下一般式（1）表示的化合物，或其盐或水合物：其中R1代表可被取代的C1-C6烷基或C2-C6炔基，或可被取代的苯基，R2代表氢原子或C1-C6烷基，R3代表甲基或乙基基团，R4代表C1-C6烷基，R5代表氢原子，但其中R1为未取代或取代为卤素原子的C1-C6烷基，且R2为氢原子的化合物除外。

  公开号：

  WO2005103049A1
• 作为产物：
  描述：

  2-氯-3-甲基-5-硝基吡啶 在 过氧化脲素 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 2,6-二氯-3-甲基-5-硝基吡啶
  参考文献：
  名称：

  NITROGENATED HETEROCYCLIC COMPOUND

  摘要：

  公开号：

  EP2848618B1

文献信息

• Use of EP4 receptor ligands in the treatment of IL-6 involved diseases
  申请人：——

  公开号：US20030236260A1

  公开（公告）日：2003-12-25

  Methods of treating IL-6 involved diseases with EP4 receptor ligands, including EP4 receptor antagonists. Assays to determine the effect of test compounds on PGE2-induced whole blood cells activation.

  治疗IL-6相关疾病的方法涉及EP4受体配体，包括EP4受体拮抗剂。用于确定试验化合物对PGE2诱导的全血细胞活化效果的测定。
• Flupirtine and retigabine as templates for ligand-based drug design of K_V7.2/3 activators
  作者：Abdrrahman S. Surur、Christian Bock、Kristin Beirow、Konrad Wurm、Lukas Schulig、Markus K. Kindermann、Werner Siegmund、Patrick J. Bednarski、Andreas Link

  DOI：10.1039/c9ob00511k

  日期：——

  of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically

  药物性肝损伤（DILI）和组织变色分别导致密切相关的药物氟吡汀和瑞替加滨的治疗最近中断。这些药物获得的经验强烈表明，异四聚体，电压门控钾通道2和3（K V 7.2 / 3）是有效治疗疼痛和癫痫的有效靶点。由于不良反应与作用机理无关，因此研究这些经过临床验证的药物样前导物的化学修饰似乎很有希望。在目前的逆代谢药物设计研究中，合成了一系列43种化合物，并针对K V 7.2 / 3的打开活性和功效进行了表征。活性最高的化合物22d作为K V 7.2 / 3开瓶器，具有出色的效力（EC 50 = 4 nM）和功效（154％）。在高于63μM的浓度下，有限的水溶性阻碍了毒性测试，但是该浓度对培养中的两种肝细胞系（HEP-G2和TAMH）无毒。活性稍差但更易溶的化合物25b（EC 50 = 11 nM，功效111％）与氟吡汀相比，毒性/活性比提高了三个数量级，并代表了引人注目的铅结构，可用于开发更安全的镇痛药和抗癫痫药。
• EP4 receptor inhibitors to treat rheumatoid arthritis
  申请人：——

  公开号：US20020077329A1

  公开（公告）日：2002-06-20

  The invention features a method of treating rheumatoid arthritis in a mammal comprising administering an agent that inhibits prostaglandin EP4 receptor (EP4) activity. Also featured is a method of identifying agents that selectively inhibit EP4 activity in vivo.

  该发明涉及一种治疗哺乳动物类风湿性关节炎的方法，包括给予一种抑制前列腺素EP4受体（EP4）活性的药物。还涉及一种识别在体内选择性抑制EP4活性的药物的方法。
• [EN] IMIDAZO [1,2-B] PYRIDAZINE AND IMIDAZO [4,5-B] PYRIDINE DERIVATIVES AS JAK INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZO[1,2-B]PYRIDAZINE ET D'IMIDAZO[4,5-B]PYRIDINE EN TANT QU'INHIBITEURS DES JAK
  申请人：ALMIRALL SA

  公开号：WO2012069202A1

  公开（公告）日：2012-05-31

  New imidazo[1,2-b]pyridazine and imidazo[4,5-b]pyridine derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).

  揭示了具有化学结构式（I）的新咪唑并[1,2-b]吡啶嗪和咪唑并[4,5-b]吡啶衍生物；以及它们的制备方法、包含它们的药物组合物以及它们作为Janus激酶（JAK）抑制剂在治疗中的用途。
• Sulfide Analogues of Flupirtine and Retigabine with Nanomolar K _V 7.2/K _V 7.3 Channel Opening Activity
  作者：Christian Bock、Abdrrahman S. Surur、Kristin Beirow、Markus K. Kindermann、Lukas Schulig、Anja Bodtke、Patrick J. Bednarski、Andreas Link

  DOI：10.1002/cmdc.201900112

  日期：2019.5.6

  Sulfide analogues were identified that are devoid of the risk of quinone formation, but possess potent KV 7.2/3 opening activity. For example, flupirtine analogue 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50 =1.4 nm), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

  钾通道开放剂氟吡汀和瑞替加滨已被证明是有价值的镇痛药或抗癫痫药。它们最近分别由于偶发的肝毒性和组织变色而退出治疗，这使得治疗领域没有被填补。两种药物的代谢氧化都会导致亲电子醌的形成。在长期摄入瑞替加滨后发生氟吡汀和蓝色组织变色的情况下，这些难以捉摸的，高反应性的代谢物可能引起肝损伤。我们研究了可以改变哪些结构特征，以避免芳香环的有害氧化，并使氧化向更良性代谢物的形成转移。进行了结构活性关系研究，以评估45种衍生物的KV 7.2 / 3通道开放活性。鉴定出硫化物类似物没有形成醌的风险，但具有有效的KV 7.2 / 3打开活性。例如，氟吡汀类似物3-（3,5-二氟苯基）-N-（6-（异丁硫基）-2-（吡咯烷-1-基）吡啶-3-基）丙酰胺（48）具有100倍的增强活性（ EC50 = 1.4 nm），大大提高了毒性/活性比，并具有与体外瑞替加滨相同的功效。