4,4'-二氰基-2,2'-二嘧啶 | 67491-43-4

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 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: 4,4'-二氰基-2,2'-二嘧啶
• 英文名称: 4,4'-dicyano-2,2'-bipyridine
• 英文别名: 2-(4-cyanopyridin-2-yl)pyridine-4-carbonitrile
• CAS: 67491-43-4
• 化学式: C₁₂H₆N₄
• 分子量: 206.206
• InChiKey: IUMFOUVCDJGKNS-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  391.2±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于室温且在惰性气体保护下

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,4’-Dicyano-2,2’-bipyridine
Synonyms: 2-(4-Cyanopyridin-2-yl)pyridine-4-carbonitrile

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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: 4,4’-Dicyano-2,2’-bipyridine
CAS number: 67491-43-4

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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: C12H6N4
Molecular weight: 206.2

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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

反应信息

• 作为反应物：
  描述：

  4,4'-二氰基-2,2'-二嘧啶 在 氨 、 sodium methylate 、 氯化铵 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 2,2''-Bipyridine-4,4''-dicarboximidamide
  参考文献：
  名称：

  S-Adenosylmethionine decarboxylase inhibitors: new aryl and heteroaryl analogs of methylglyoxal bis(guanylhydrazone)

  摘要：

  A series of 3-acylbenzamidine (amidino)hydrazones 7a-h, the corresponding (hetero)aromatic congeners 7i-p, and 3,3'-bis-amidino-biaryls 25a-e were synthesized. The hydrazones 7a-p were prepared by conversion of the corresponding acyl nitriles 1a,c-di,n-p to the imido esters 3a,c-d,i and the amidines 5a,c-d,h-i, followed by a reaction with aminoguanidine, or vice versa. Similarly, the biaryl 3,3'-dinitriles 23a-e were converted, via the imino esters 24a-c or the imino thioesters 27d-e, to the diamidines 25a-e. These new products are conformationally constrained analogues of methylglyoxal bis(guanylhydrazone)(MGBG). They are up to 100 times more potent as inhibitors of rat liver S-adenosylmethionine decarboxylase (SAMDC) and generally low potent inhibitors of rat small intestine diamine oxidase (DAO) than MGBG. Some of these SAMDC inhibitors, eg., compounds 7a, 7e, 7i, 25a, and 25d, have shown antiproliferative effects against T24 human bladder carcinoma cells. These products, whose structure-activity relationships are discussed, are of interest as potential anticancer agents and drugs for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00053a007
• 作为产物：
  描述：

  2,2'-联吡啶-4,4'-二甲酸 在 氨 、 三氯氧磷 作用下， 反应 61.0h， 生成 4,4'-二氰基-2,2'-二嘧啶
  参考文献：
  名称：

  Bipyridinedicarbonitrile complexes of molybdenum and tungsten

  摘要：

  DOI：

  10.1016/0022-328x(88)89021-1
• 作为试剂：
  描述：

  2-溴-2-甲基丙酸乙酯 、 2-乙烯基喹啉 、 苯硼酸 在 potassium carbonate 、 4,4'-二氰基-2,2'-二嘧啶 、 nickel dichloride 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 以68 %的产率得到ethyl 2-methyl-4-phenyl-4-(quinolin-2-yl)butanoate
  参考文献：
  名称：

  镍催化烯基N-杂芳烃的三组分烷基化

  摘要：

  报道了镍催化的烯基N-杂芳烃与 α-溴代羧酸酯和芳基硼酸的三组分烷基芳基化反应。该方案提供了一种以中等至良好产率获得各种N-杂芳烃取代的二芳基烷烃的新方法。其具有反应条件温和、镍催化剂廉价、底物易得、底物范围广泛等特点。

  DOI：

  10.1021/acs.orglett.3c03474

文献信息

• ビピリジル化合物の製造方法
  申请人：国立大学法人名古屋大学

  公开号：JP2017132738A

  公开（公告）日：2017-08-03

  【課題】様々なビピリジル化合物を、工程数が少なく、緩和な条件且つ短時間の反応により得る。【解決手段】パラジウム化合物及び酸化剤の存在下に、一般式：［式中、Ｙは水素原子又は窒素原子を示す。Ｒ１は、シアノ基、ハロゲン原子、置換されていてもよいアルキル基、置換されていてもよいアルコキシ基、置換されていてもよいアリール基、置換されていてもよいヘテロアリール基、又は置換されていてもよいシリル基を示す。ｎは０〜４の整数を示す。ｎが２以上である場合、同じベンゼン環に結合する２個のＲ１が互いに結合して環を形成してもよい。］で表される化合物を反応させる。【選択図】なし

  【课题】通过较少的步骤数、温和的条件以及短时间反应获得各种不同的 bipiridine 化合物。 【解决手段】在钯化合物和氧化剂的存在下，使具有一般式：[式中，Y代表氢原子或氮原子。R1代表氰基、卤素原子、可以被取代的烷基、可以被取代的环烷氧基、可以被取代的芳基、可以被取代的杂芳基，或者可以被取代的硅基。n代表0至4的整数。当n大于或等于2时，连接到同一苯环的两个R1可以相互连接形成环。] 的化合物发生反应。 【选择图】无
• Re ^I Tricarbonyl Complexes as Coordinate Covalent Inhibitors for the SARS‐CoV‐2 Main Cysteine Protease
  作者：Johannes Karges、Mark Kalaj、Milan Gembicky、Seth M. Cohen

  DOI：10.1002/anie.202016768

  日期：2021.5.3

  syndrome—coronavirus 2 (SARS‐CoV‐2) has impacted the quality of life and cost hundreds‐of‐thousands of lives worldwide. Based on its global spread and mortality, there is an urgent need for novel treatments which can combat this disease. To date, the 3‐chymotrypsin‐like protease (3CLpro), which is also known as the main protease, is considered among the most important pharmacological targets. The vast majority

  自爆发以来，严重急性呼吸系统综合症冠状病毒 2 (SARS-CoV-2) 影响了生活质量，并导致全世界数十万人丧生。鉴于其在全球的传播和死亡率，迫切需要能够对抗这种疾病的新疗法。迄今为止，3-胰凝乳蛋白酶样蛋白酶（3CL pro ）也被称为主要蛋白酶，被认为是最重要的药理学靶点之一。绝大多数研究的 3CL前体抑制剂都是有机非共价结合剂。在此，建议使用无机配位共价结合剂来减弱蛋白酶的活性。 Re 三羰基复合物被鉴定为 3CL pro的协调共价酶抑制。初步研究表明 3CL pro对几种人类蛋白酶具有选择性抑制作用。这项研究首次展示了金属配合物作为 3CL半胱氨酸蛋白酶抑制剂的例子。
• STEREOSELECTIVE PROCESS FOR PREPARING SUBSTITUTED POLYCYCLIC PYRIDONE DERIVATIVES
  申请人：Shionogi & Co., Ltd.

  公开号：US20200247818A1

  公开（公告）日：2020-08-06

  The present invention provides industrially suitable processes for preparing intermediates in the production of substituted polycyclic pyridone derivatives having a cap-dependent endonuclease inhibitory activity. In the process as shown below, wherein each symbol is as defined in the specification, an optically active substituted tricyclic pyridone derivative of the formula (VII) is obtained in high yield and high enantioselectivity by subjecting a compound of the formula (III) or (VI) to intramolecular cyclization with controlling stereochemistry to obtain a compound of the formula (IV) having a removable functional group on an asymmetric carbon, and then removing the functional group thereof.

  本发明提供了在制备具有依赖CAP末端核酸酶抑制活性的取代多环吡啶酮衍生物的生产中的工业适用过程。在下面所示的过程中，其中每个符号如规范中定义，通过将式（III）或（VI）的化合物经过控制立体化学的分子内环化得到具有可移除手性碳上的可移除官能团的式（IV）的化合物，然后去除其官能团，以高产率和高对映选择性获得式（VII）的手性取代三环吡啶酮衍生物。
• A Systematic Study of the Effects of Complex Structure on Aryl Iodide Oxidative Addition at Bipyridyl‐Ligated Gold(I) Centers
  作者：Jamie A. Cadge、John F. Bower、Christopher A. Russell

  DOI：10.1002/anie.202108744

  日期：2021.11.15

  An assessment of the effects of complex structure on the oxidative addition mechanism of aryl iodides at bipyridyl-ligated AuI-centers is described. It is shown that the hemilability of the bipy ligand and the electropositivity of the Au-center are important factors, leading to facile oxidative addition with electron-poor ligands and electron-rich aryl iodides. These unusual observations contrast established

  描述了复杂结构对联吡啶连接的金中心处芳基碘化物氧化加成机制的影响的评估。结果表明，联吡啶配体的半稳定性和Au中心的正电性是重要因素，导致贫电子配体和富电子芳基碘化物易于氧化加成。这些不寻常的观察结果与已建立的钯基系统形成鲜明对比。
• Synthesis of Ligands Based on 4 <i>H</i> ‐Imidazoles and Pyridine Subunits: Selective Complexation and Bathochromically Absorbing Complexes
  作者：Jörg Blumhoff、Rainer Beckert、Sven Rau、Sebastian Losse、Martin Matschke、Wolfgang Günther、Helmar Görls

  DOI：10.1002/ejic.200800914

  日期：2009.5

  New multifunctional ligands based on the combination of 4H-imidazoles with pyridine subunits have been synthesised. The long wavelength absorptions originating fromthe merocyanine-chromophore can be shifted towards the near infrared (NIR) region by introduction of additionalauxochromic groups. Due to different complexation spheres these hybrid-ligands form the requirements for the construction of heterobimetallic

  已经合成了基于 4H-咪唑与吡啶亚基组合的新型多功能配体。源自部花青发色团的长波长吸收可以通过引入额外的辅助变色基团向近红外 (NIR) 区域移动。由于不同的络合球体，这些杂化配体形成了构建异双金属配合物的要求。此外，杂化配体是氧化还原活性化合物，显示出两个分离的完全可逆还原。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)