3,6-二(1H-咪唑并L-1-基)哒嗪 | 177648-99-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 哒嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3,6-二(1H-咪唑并L-1-基)哒嗪
• 中文别名: 3,6-双(1H-1-咪唑)哒嗪
• 英文名称: 3,6-bis(imidazol-1-yl)pyridazine
• 英文别名: 3,6-bis(N-imidazolyl)pyridazine；3,6-Di(1H-imidazol-1-yl)pyridazine；3,6-di(imidazol-1-yl)pyridazine
• CAS: 177648-99-6
• 化学式: C₁₀H₈N₆
• mdl: MFCD09475834
• 分子量: 212.214
• InChiKey: HGHPOOTWIHFSSF-UHFFFAOYSA-N

物化性质

• 沸点：
  528.9±35.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,6-Di(1H-imidazol-1-yl)pyridazine
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: 3,6-Di(1H-imidazol-1-yl)pyridazine
CAS number: 177648-99-6

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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: C10H8N6
Molecular weight: 212.2

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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：

  3,6-二(1H-咪唑并L-1-基)哒嗪 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 29.0h， 生成 [Ni(3-(1-(2-pyridylmethyl)imidazol-2-yliden-3-yl)-6-methoxypyridazine)₂](PF₆)₂
  参考文献：
  名称：

  Pyridazine-Based N-Heterocyclic Carbene Complexes and Ruthenium-Catalyzed Oxidation Reaction of Alkenes

  摘要：

  [Ru2Cl(L)(CH3CN)(4)](PF6)(3) (1, L = 3,6-bis(N-(pyridylmethyl)imidazolylidenyl)pyridazine), [Cu3L3a](-)(PF6)(3) (2, L-a = 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl)imidazoyonyl)pyridazine), [Pd-2(allyl)(2)L](PF6)(2) (3), [Pd-2(allyl)(2)L-2(b)](PF6)(2) (4, L-b = N-pyridylmethyl-imidazole), and [NiL2c](PF6)(2) (5, L-c = 3-(N-(pyridylmethyl)imidazolylidenyl)-6-methoxylpyridazine) have been synthesized and fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction analysis. In complex 1, ligand L binds to two Ru(II) centers, forming a well-behaved Ru-2(L)Cl plane with a five-membered metallocyclic ring. Complex 2 is trinuclear, containing a triangular Cu-3 unit bonded together by three 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl)imidazolylonyl)pyridazine, where one imidazolylidene was oxidized into imidazolone. Deprotonation reaction with Ag2O in CH3CN and CH3OH resulted in C-N cleavage of the imidazolium salt, and subsequent reaction with [Pd(allyl)Cl](2) and Ni(PPh3)(2)Cl-2 gave 4 and 5, respectively. Dinuclear Ru(II)-NHC complex 1 exhibits excellent catalytic activity for the oxidation of alkenes into diketones.

  DOI：

  10.1021/om300644h
• 作为产物：
  描述：

  咪唑 、 3,6-二氯哒嗪 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 以80%的产率得到3,6-二(1H-咪唑并L-1-基)哒嗪
  参考文献：
  名称：

  基于双（咪唑/苯并咪唑-1-基）哒嗪配体的六种配合物：合成、结构和性质

  摘要：

  摘要 本文报道了六种新的 Ni(II)/Cu(II)/Zn(II) 配合物，即 [Ni(L1)4(OH)2] (1)、[Cu(L1)4(OH)2] (2), [Cu(L1)2(SiF6)]n (3), {[Cu(L2)(HCOO)2]·H2O·CH3OH}n (4), [Ni(L2)2(NO3)2 ]n (5) 和 {[Zn(L2)Cl2]·DMF}n (6) (L1 = 3,6-双(咪唑-1-基)哒嗪，L2 = 3,6-双(苯并咪唑-1- yl)哒嗪)，通过单晶 X 射线衍射、元素分析、IR、PXRD 对其进行表征。这些配合物已在界面扩散过程、加热回流或水热条件下成功构建。1和2的结构是单核配合物。复合体 3 展示了一个 6 连通的 3D 拓扑网络，其 Schlafli 符号为 (412·63)。在配合物4中，两个Cu(II)通过两个HCOO−阴离子连接形成双核结构单元，通过μ2-L2配体排列成一维梯状结构。

  DOI：

  10.1016/j.molstruc.2016.08.051

文献信息

• Cobalt(II) complexes with bis(N-imidazolyl/benzimidazolyl) pyridazine: Structures, photoluminescent and photocatalytic properties
  作者：Jin-Ping Li、Jian-Zhong Fan、Duo-Zhi Wang

  DOI：10.1016/j.jssc.2016.04.037

  日期：2016.7

  Abstract Six new Co II complexes [Co( L 1 ) 4 (OH) 2 ] (1), [Co( L 1 )(H 2 O) 4 ]·2ClO 4 } ∞ (2), [Co( L 1 )(H 2 O) 4 ]·SiF 6 } ∞ (3), [Co( L 1 ) 3 ]·2ClO 4 } ∞ (4), [Co( L 2 )Cl 2 ] ∞ (5) and [Co( L 2 ) 2 ]·SiF 6 } ∞ (6) [ L 1 =3,6-bis( N -imidazolyl) pyridazine, L 2 =3,6-bis ( N -benzimidazolyl) pyridazine] have been synthesized and characterized by elemental analysis, IR spectra and single crystal

  摘要 六种新型Co II配合物[Co( L 1 ) 4 (OH) 2 ] (1), [Co( L 1 )(H 2 O) 4 ]·2ClO 4 } ∞ (2), [Co( L 1)(H 2 O) 4 ]·SiF 6 } ∞ (3), [Co( L 1 ) 3 ]·2ClO 4 } ∞ (4), [Co( L 2 )Cl 2 ] ∞ (5)和[Co(L 2 ) 2 ]·SiF 6 } ∞ (6) [ L 1 =3,6-双(N-咪唑基)哒嗪,L 2 =3,6-双(N-苯并咪唑基)哒嗪]通过元素分析、红外光谱和单晶X射线衍射进行了合成和表征。配合物 1 具有单核结构，而配合物 2 和 3 具有一维链结构。考虑到 Co II 中心通过 L 1 配体连接，配合物 4 的 3-D 框架可以合理化为具有化学计量单节点网络的 4^12.6^3} 6-c 拓扑网络。图5显示了由具有Co II中心的中性链[Co(L
• Synthesis, structures, magnetic and electric properties of four new coordination polymers constructed with heterocyclic nitrogen ligands and multidentate organic acid
  作者：Ru-Xia Yang、Hai-Ming Lan、Peng-Yin Zhu、Li-Zhen Yang、Yu-Ming Yu、Lu-Lu Wang、Duo-Zhi Wang

  DOI：10.1016/j.ica.2019.119410

  日期：2020.6

  Abstract Four new coordination polymers based on heterocyclic nitrogen and aromatic carboxylic acids, namely [Co(L1)(2,5-TDC)(H2O)]n (1), [Co(L1)(1,3-BDC)]n (2), [Cu(L2)(1,4-NDC)]n (3), and [Mn(L2)2(2-AIOC)(H2O)]n (4) [L1 = 3,6-bis(1H-imidazol-1-yl)pyridazine, L2 = 3,6-bis(1H-benzo[d]imidazol-1-yl) pyridazine, 1,2-H2TDC = 2,5-thiophenedicarboxylic acid, 1,3-H2BDC = benzenedicarboxylic acid, 1,4-H2NDC = 1

  摘要四种基于杂环氮和芳族羧酸的新型配位聚合物，即[Co（L1）（2,5-TDC）（H2O）] n（1），[Co（L1）（1,3-BDC）] n （2），[Cu（L2）（1,4-NDC）] n（3）和[Mn（L2）2（2-AIOC）（H2O）] n（4）[L1 = 3,6-bis （1H-咪唑-1-基）哒嗪，L2 = 3,6-双（1H-苯并[d]咪唑-1-基）哒嗪，1,2-H2TDC = 2,5-噻吩二甲酸，1,3- [H2BDC ＝苯二甲酸，1，4-H2NDC ＝ 1，4-萘二甲酸，2-H2AlOC ＝ 2-氨基对苯二甲酸]已经被水-/溶剂热制备并进一步表征。图1和2显示了分别属于典型sql和sp拓扑网络的2D平面结构。3是具有pcu拓扑网的六连接3D框架，而4是通过氢键构造的3D超分子结构。磁测试表明1-3存在反铁磁行为，而4显示出亚铁磁行为。电化学测量结果表明3具有出色的循环稳定性，在2
• A series of new mixed-ligand complexes based on 3,6-bis(imidazol-1-yl)pyridazine: syntheses, structures, and catalytic activities
  作者：Sheng-Bin Zhou、Xin-Fang Wang、Ceng-Ceng Du、Duo-Zhi Wang、Dianzeng Jia

  DOI：10.1039/c7ce00394c

  日期：——

  units (SBUs). Complex 3 presents an 8-connected sqc3 3D framework based on a chair-shaped [Cu4(μ3-OH)4]4+ SBU with a Schläfli symbol of 424·64}. Complex 4 displays a 3D framework with diamondoid topology, which includes L/Ni(II)/L helical chains. Complex 5 features a 1D chain structure formed by L ligands. Complex 6 shows a dinuclear structure, which is arranged into a 1D supramolecular chain by hydrogen-bonding

  基于L的七个新的混合配体配合物[ L = 3,6-双（咪唑-1-基）哒嗪]，即[Ni（L）2（SCN）2 ] n（1），[Cu 5（L）（1,2-BDC）4（μ 3 -OH）2 ] ñ（2），[铜4（大号）2（1,3- HBDC）（1,3-BDC）（μ 3 -OH）4 ]·ClO 4 ·2.6H 2 O} n（3），[Ni（L）（1,4-BDC）H2 O]·0.25H 2 O} n（ 4），[Co（ L）（1,3,5-H 2 BTC） 2 H 2 O] n（ 5），[Cu 2（ L）（2， 6-PYDC） 2（H 2 O） 2 ]·4.4H 2 O} n（ 6）和[Co（ L）（4,4'-OBA）]·3.725H 2 O} n（ 7）[ 1,2-苯二甲酸（1,2-H 2 BDC），1,3-苯二甲酸（1,3-H 2BDC），1,4-苯二甲酸（1,4-H 2 BDC），1,3,5-苯三甲酸（1
• Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives
  作者：Gerd Steiner、Josef Gries、Dieter Lenke

  DOI：10.1021/jm00133a013

  日期：1981.1

  examined on normotensive and spontaneously hypertensive rats by comparison with dihydralazine (I). 6-Imidazol-1-yl derivatives have proved particularly active. Of these derivatives, 3-hydrazino-6-(2-methylimidazol-1-yl)pyridazine (7c) achieves 4.9 times the activity of dihydralazine when administered orally to spontaneously hypertensive rats. The LD50 values of 7c and dihydralazine are very similar.

  描述了具有抗高血压作用的新型6-杂芳基-3-肼基哒嗪的合成和药理活性。通过三种不同的合成方法将吡咯，吡唑，咪唑，三唑，四唑，噻吩，吲哚和咔唑杂环引入到哒嗪核的6位。通过与二肼苯哒嗪（I）进行比较，对降压和自发性高血压大鼠的降压作用进行了检查。已证明6-咪唑-1-基衍生物具有特别的活性。在这些衍生物中，当对自发性高血压大鼠口服时，3-肼基-6-（2-甲基咪唑-1-基）哒嗪（7c）的活性是二肼苯哒嗪的4.9倍。7c和二肼苯哒嗪的LD50值非常相似。
• Solvothermal syntheses, structures and fluorescent properties of six ZnII/CdII coordination polymers constructed from N-donor ligands and multidentate organic acid
  作者：Jun-Liang Dong、Fei Xie、Jia-Qiang Du、Ru-Xia Yang、Hai-Ming Lan、Duo-Zhi Wang

  DOI：10.1016/j.jssc.2018.11.039

  日期：2019.2

  4-tricarboxylic acid, D-CAM = (1 R,3 S)−1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid, 1,3,5-H3BTC = benzene-1,3,5-tricarboxylic acid, 4,4´-H2OBA = 4,4´-oxydibenzoic acid) were achieved by reactions of the corresponding metal salt with mixed organic ligands. Their structures were determined by single-crystal X-ray diffraction, IR spectra, elemental analysis, powder X-ray diffraction and thermogravimetric analysis

  六种新的配位聚合物（CPs）[Cd（L 1）（CHDA）]·H 2 O} n（1），[Zn 3（L 1）2（1,2,4-BTC）2（H 2 O ）4 ] n（2），[Zn（L 2）（D-CAM）（H 2 O）] n（3），[Zn 3（L 2）（1,2,4-BTC）2（H 2 O）4 ] n（4），[Cd（L 2）（1,3,5-HBTC）] n（5）和[Zn（L 2）（4,4´-BOA）]·H 2 O} n（6）（L 1 = 3,6-bis （咪唑-1-基）哒嗪，L 2 = 3,6-双（苯并咪唑-1-基）哒嗪，1,4-H 2 CHDA =（1 S，4 S）-环己烷-1,4-二羧酸，1,2,4-H 3 BTC =苯-1,2,4-三羧酸，D-CAM =（1 R，3 S）-1,2,2-三甲基环戊烷-1,3-二羧酸，1 ，3,5-H 3 BTC =苯-1,3,5-三羧酸，4,4´-H 2