2,6-二溴异烟酸甲酯 | 119308-57-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 2,6-二溴异烟酸甲酯
• 中文别名: 2,6-二溴-4-羧酸甲酯吡啶
• 英文名称: methyl 2,6-dibromoisonicotinate
• 英文别名: 2,6-dibromo-4-(methoxycarbonyl)pyridine；methyl 2,6-dibromopyridine-4-carboxylate
• CAS: 119308-57-5
• 化学式: C₇H₅Br₂NO₂
• 分子量: 294.93
• InChiKey: XGHFPTMUVIDZNF-UHFFFAOYSA-N

物化性质

• 熔点：
  86.8-88.2 °C(Solv: hexane (110-54-3))
• 沸点：
  320.9±37.0 °C(Predicted)
• 密度：
  1.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 2,6-dibromopyridine-4-carboxylate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2,6-dibromopyridine-4-carboxylate
CAS number: 119308-57-5

---

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.
Store in closed vessels, refrigerated.
Storage:

---

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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H5Br2NO2
Molecular weight: 294.9

---

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.

---

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：

  2,6-二溴异烟酸甲酯 在 sodium methylate 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 以691 g的产率得到2-溴-6-甲氧基-4-吡啶羧酸甲酯
  参考文献：
  名称：

  新型局部抗雄激素上油系统的工艺开发和结晶

  摘要：

  描述了一种获得新的局部抗雄激素的（S）-N-（2-溴-6-甲氧基吡啶-4-基）-2-羟基-2,4-二甲基戊酰胺1的有效途径。目标化合物已由公斤规模生产，从citrazinic acid的总收率达25％（HPLC纯度为98.8％，ee > 99％ee）。使用临时保护基团促进氨基吡啶4和α-羟基酸6之间的关键酰胺偶联，以促进酰氯的形成。氨基吡啶4由市售的citrazinic acid通过溴化磷（V）溴化二溴化物，然后用单核苷S N制备而成。Ar与甲醇钠反应，最后进行霍夫曼重排。使用对映选择性氰基硅烷化，然后用（S）-α-甲基苄基胺进行盐拆分，得到对映纯α-羟基酸6。化合物1的绝对构型是通过反常散射确定的，API的最终结晶是在晶种温度低于单晶温度下进行晶种注入后得到的，其结晶粉末呈“沙漠玫瑰”形团簇。

  DOI：

  10.1021/acs.oprd.6b00392
• 作为产物：
  描述：

  柠嗪酸 在 三溴氧磷 作用下， 反应 17.0h， 生成 2,6-二溴异烟酸甲酯
  参考文献：
  名称：

  胰蛋白酶和凝血酶结合过程中蛋白质诱导的配体质子化变化：是否暗示两种蛋白质的选择性决定因素不同？

  摘要：

  胰蛋白酶和凝血酶是结构相似的丝氨酸蛋白酶，可识别不同的底物。凝血酶在Arg后裂解，而胰蛋白酶在Lys / Arg后裂解。两者都通过S1口袋底部的Asp189识别基本的基板头基。通过晶体学和等温滴定热法（ITC），我们研究了一系列d -Phe / d-DiPhe-Pro-（氨基）吡啶。相同的配体对显示相同的结合姿势。出人意料的是，一种配体在P1处以质子化状态的胰蛋白酶和未质子化状态的凝血酶结合，并残留溶剂化方式不同。虽然胰蛋白酶结合是由有序的水分子介导的，但在凝血酶中，水却分散在三个水合位点上。尽管具有高度相似的S1口袋，我们的结果表明Asp189的不同静电性质可能有助于选择性的决定因素。凝血酶与胰蛋白酶中不存在的Asp189旁的特定Na +离子结合。凝血酶中S1边缘的带电Glu192进一步削弱了整个S1袋的静电特性，而胰蛋白酶中的不带电Gln192代替了该电荷。

  DOI：

  10.1021/acs.jmedchem.9b02061

文献信息

• [EN] BIPYRIDYLAMINOPYRIDINES AS SYK INHIBITORS<br/>[FR] BIPYRIDYLAMINOPYRIDINES EN TANT QU'INHIBITEURS DE SYK
  申请人：MERCK SHARP & DOHME

  公开号：WO2012154518A1

  公开（公告）日：2012-11-15

  The present invention provides novel pyrimidine amines of formula I which are potent inhibitors of spleen tyrosine kinase, or are prodrugs thereof, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD and rheumatoid arthritis and cancer.

  本发明提供了式I的新颖嘧啶胺，它们是脾酪氨酸激酶的强效抑制剂，或者是其前药，并且可用于治疗和预防由所述酶介导的疾病，如哮喘、慢性阻塞性肺病（COPD）、类风湿性关节炎和癌症。
• Rational Approach to Plasmonic Dimers with Controlled Gap Distance, Symmetry, and Capability of Precisely Hosting Guest Molecules in Hotspot Regions
  作者：Li Tian、Chen Wang、Hongwei Zhao、Fuwei Sun、Hao Dong、Kai Feng、Peng Wang、Guokang He、Guangtao Li

  DOI：10.1021/jacs.0c13377

  日期：2021.6.16

  Plasmonic dimers not only provide a unique platform for studying fundamental plasmonic behavior and effects but also are functional materials for numerous applications. The efficient creation of well-defined dimers with flexible control of structure parameters and thus tunable optical property is the prerequisite for fully exploiting the potential of this nanostructure. Herein, based on a polymer-assisted

  等离子体二聚体不仅为研究基本等离子体行为和效应提供了独特的平台，而且还是许多应用的功能材料。通过灵活控制结构参数和可调光学特性，有效创建定义明确的二聚体是充分利用这种纳米结构潜力的先决条件。在此，基于与分子笼化学共轭的聚合物辅助自组装方法，展示了一种策略，用于构建具有受控尺寸、组成、形状、对称性和粒子间间隙分离的笼桥等离子体二聚体，以模块化和高产量方式。具有高度的自由度和可控性，该策略允许轻松访问具有小于 5 nm 间隙距离和定制光学特性的各种对称/不对称二聚体。重要的是，作为两个组成元素的连接，嵌入连接处的分子笼使组装的二聚体能够在热点区域精确和可逆地承载丰富的客体分子，为创造各种等离子体介导的应用提供了巨大的潜力。
• A robust hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex: Synthesis and its catalytic application towards Suzuki–Miyaura couplings in aqueous solvents
  作者：Tao Tu、Xike Feng、Zhixun Wang、Xiyu Liu

  DOI：10.1039/c0dt01083a

  日期：——

  A novel hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex (3) acted as a highly efficient robust recyclable molecular catalyst towards Suzuki–Miyaura coupling reactions in aqueous media and tolerated various functional groups (even heterocycles) with extremely low catalyst loading.

  新型亲水吡啶桥 双苯并咪唑基亚钯pincer配合物（3）在水性介质中可作为Suzuki-Miyaura偶联反应的高效耐用的可循环分子催化剂，并以极低的催化剂负载量耐受各种官能团（甚至是杂环）。
• [EN] 2,4'-BIPYRIDINYL COMPOUNDS AS PROTEIN KINASE D INHIBITORS USEFUL FOR THE TREATMENT OF IA HEART FAILURE AND CANCER<br/>[FR] COMPOSÉS DE 2,4'-BIPYRIDINYLE COMME INHIBITEURS DE LA PROTÉINE KINASE D UTILES POUR LE TRAITEMENT DE L'INSUFFISANCE CARDIAQUE ET DU CANCER
  申请人：NOVARTIS AG

  公开号：WO2009150230A1

  公开（公告）日：2009-12-17

  The present invention provides novel organic compounds of Formula I: methods of use, and pharmaceutical compositions thereof.

  本发明提供了式I的新型有机化合物：其使用方法和药物组合物。
• [EN] RSV INHIBITING 3-SUBSTITUTED QUINOLINE AND CINNOLINE DERIVATIVES<br/>[FR] DÉRIVÉS DE QUINOLÉINE ET DE CINNOLINE SUBSTITUÉS EN 3 INHIBANT LE VRS
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2021214136A1

  公开（公告）日：2021-10-28

  The invention concerns compounds of formula (I) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention further concerns pharmaceutical compositions comprising these compounds and the compounds for use in the treatment of respiratory syncytial virus infection.

  这项发明涉及具有抗病毒活性的式(I)化合物，特别是对呼吸道合胞病毒(RSV)复制具有抑制活性的化合物。该发明还涉及包含这些化合物的药物组合物，以及用于治疗呼吸道合胞病毒感染的化合物。