3-氯-6-(3,5-二甲基-1H-吡唑-1-基)哒嗪 | 29334-67-6

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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-氯-6-(3,5-二甲基-1H-吡唑-1-基)哒嗪
• 中文别名: 3-氯-6-(3,5-二甲基-1H-吡唑)哒嗪
• 英文名称: 3-chloro-6-(3,5-dimethylpyrazol-1-yl)pyridazine
• 英文别名: 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazine
• CAS: 29334-67-6
• 化学式: C₉H₉ClN₄
• mdl: MFCD00112281
• 分子量: 208.65
• InChiKey: OVXSFTFBSBIDMM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114
• 沸点：
  380.2±42.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

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-Chloro-6-(3,5-dimethyl-1H-pyrazol-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-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazine
CAS number: 29334-67-6

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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, refrigerated.
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: C9H9ClN4
Molecular weight: 208.6

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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 chloride.

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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-氯-6-(3,5-二甲基-1H-吡唑-1-基)哒嗪 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以80%的产率得到3-chloro-6-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)pyridazine
  参考文献：
  名称：

  Synthesis, Antibacterial and Antioxidant Properties of Pyrazolylpyridazines

  摘要：

  A number of 6-chloro-3-(pyrazol-1'-yl) pyridazines were prepared from 3,6-dichloropyridazine via either reaction with hydrazine followed by reaction with appropriate reagents to develop the pyrazole or through a nucleophilic reaction with a pyrazole. Some electrophilic reactions gave the corresponding 4'-substituted pyrazolylpyridazines. All the compounds were tested for their in vitro antibacterial as well as their antioxidant properties.

  DOI：

  10.14233/ajchem.2013.14590
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 3,6-二氯哒嗪 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-氯-6-(3,5-二甲基-1H-吡唑-1-基)哒嗪
  参考文献：
  名称：

  新型哒嗪桥联 NHC/吡唑配体及其序列银 (I) 配位

  摘要：

  制备了一系列新的哒嗪桥连 NHC/吡唑配体前体 HL1-5 并对其进行了充分表征，包括通过 XRD {HL1 = 3-[3-(2,6-二异丙基苯基)-3H-咪唑鎓-1-基]-6 -(3-pyridin-2-yl-pyrazol-1-yl)-pyridazine, HL2 = 3-[3-(2,4,6-trimethylphenyl)-3H-imidazolium-1-yl]-6-(3-吡啶-2-基-吡唑-1-基)-哒嗪，HL3 = 3-[3-(2,4,6-三甲基苯基)-3H-咪唑鎓-1-基]-6-(3,5-二甲基吡唑- 1-基)-哒嗪，HL4 = 3-(3-叔丁基-3H-咪唑鎓-1-基)-6-(3,5-二甲基吡唑-1-基)-哒嗪，HL5 = 3-[3- (2,4,6-三甲基苯基)-3H-咪唑鎓-1-基]-6-(3-甲基-5-苯基吡唑-1-基)-哒嗪，X = PF6-或BF4-}。配体前体与 Ag2O

  DOI：

  10.1002/ejic.201100264

文献信息

• Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts
  作者：Chi Wai Cheung、David S. Surry、Stephen L. Buchwald

  DOI：10.1021/ol401612c

  日期：2013.7.19

  A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle

  描述了一种 Pd 催化的氨与多种芳基和杂芳基卤化物的芳基化方法，包括具有挑战性的五元杂环底物。通过使用庞大的联芳膦配体（L6、L7和L4）及其相应的氨基联苯钯环预催化剂（3a、3b和3c），在温和条件下或在室温下实现了将氨单芳基化成伯芳胺的出色选择性。由于该过程既不需要使用手套箱，也不需要高压氨，因此应广泛适用。
• Tetramethylammonium Fluoride Alcohol Adducts for S_NAr Fluorination
  作者：María T. Morales-Colón、Yi Yang See、So Jeong Lee、Peter J. H. Scott、Douglas C. Bland、Melanie S. Sanford

  DOI：10.1021/acs.orglett.1c01490

  日期：2021.6.4

  aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an

  亲核芳族氟化 (S N Ar) 是形成 C(sp 2 )-F 键的最常用方法之一。尽管最近取得了许多进展，但这些转化的长期限制是需要严格干燥的非质子条件来保持氟化物的亲核性并抑制副产物的产生。本报告通过利用四甲基氟化铵醇加合物 (Me 4 NF·ROH) 作为 S N Ar 氟化的氟化物来源解决了这一挑战。通过系统调整醇取代基 (R)，四甲基氟化铵叔戊醇 (Me 4 NF· t-AmylOH) 被确定为在温和方便的条件下（DMSO 中 80°C，无需干燥试剂或溶剂）下用于 S N Ar 氟化的廉价、实用且台式稳定的试剂。展示了超过 50 种（杂）芳基卤化物和硝基芳烃亲电子试剂的底物范围。
• SPIRO COMPOUND AND USE THEREOF
  申请人：Taniguchi Takahiko

  公开号：US20100069351A1

  公开（公告）日：2010-03-18

  The present invention aims to provide a novel SCD inhibitor. The present invention relate to SCD inhibitor comprising A compound represented by the formula (I) wherein R is an optionally substituted cyclic group or an optionally substituted carbamoyl group, provided that R is not an optionally substituted 7-pyrido[2,3-d]pyrimidyl group; ring A is an optionally further substituted pyridazine ring; R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 and R 14 are each independently a hydrogen atom or a substituent, or R 1 and R 11 in combination, R 2 and R 12 in combination, R 3 and R 13 in combination, or R 4 and R 14 in combination optionally form an oxo group, or R 2 and R 4 in combination optionally form a bond or an alkylene cross-linkage; m and n are each independently an integer of 0 to 2; ring B is an optionally substituted ring, provided that the two atoms constituting ring B, which are adjacent to the spiro carbon atom, are not oxygen atoms at the same time, or a salt thereof, or a prodrug thereof.

  本发明旨在提供一种新型SCD抑制剂。本发明涉及一种包括下式（I）所表示的化合物的SCD抑制剂：其中R是一个可选择取代的环基或可选择取代的氨甲酰基，但R不是一个可选择取代的7-吡啶并[2,3-d]嘧啶基团；环A是一个可选择进一步取代的吡啶并嘧啶环；R1、R2、R3、R4、R11、R12、R13和R14分别独立地是氢原子或取代基，或R1和R11的组合体，R2和R12的组合体，R3和R13的组合体，或R4和R14的组合体可选择形成氧基，或R2和R4的组合体可选择形成键或烷基交联；m和n分别独立地是0到2的整数；环B是一个可选择取代的环，但构成环B的两个与螺碳原子相邻的原子不同时为氧原子，或其盐，或其前药。
• Improved Process for the Palladium-Catalyzed C–O Cross-Coupling of Secondary Alcohols
  作者：Hong Zhang、Paula Ruiz-Castillo、Alexander W. Schuppe、Stephen L. Buchwald

  DOI：10.1021/acs.orglett.0c01668

  日期：2020.7.17

  An improved protocol for the Pd-catalyzed C–O cross-coupling of secondary alcohols is described. The use of biaryl phosphine L2 as the ligand was key to achieving efficient cross-coupling of (hetero)aryl chlorides with only a 20% molar excess of the alcohol. Additionally, we observed an unusual reactivity difference between an electron-rich aryl bromide and the analogous aryl chloride, and deuterium-labeling

  描述了一种用于Pd催化仲醇交叉偶联的改进方案。使用联芳基膦L 2作为配体是实现（杂）芳基氯与仅20摩尔摩尔过量的醇的有效交叉偶联的关键。此外，我们观察到富电子的芳基溴化物与类似的芳基氯之间存在异常的反应性差异，氘标记表明当前未确定的还原途径在解释这种差异中起重要作用。
• Synthesis of Novel 6-(3,5-Dimethyl-1H-Pyrazol-1-yl)Pyridazin-3(2H)-One Derivatives and their Preliminary Biological Evaluation
  作者：Aleksandr P. Yengoyan、Roza S. Shainova、Tiruhi A. Gomktsyan、Armen V. Karapetyan

  DOI：10.3184/174751918x15389922302823

  日期：2018.10

  Simple and accessible pathways for the synthesis of a series of novel 6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazin-3(2H)-one derivatives including compounds with a combination of a pyrazolyl-pyridazine moiety with pyrimidine, 1,3,5-triazine and 1,3,4-oxadiazole rings in the same molecules were established. The tautomeric structures of 3-oxopyridazine and 5-thioxo-1,3,4-oxadiazole rings and also the position

  合成一系列新型 6-(3,5-二甲基-1H-吡唑-1-基)哒嗪-3(2H)-one 衍生物的简单易行途径，包括具有吡唑基-哒嗪部分与嘧啶、1,3,5-三嗪和1,3,4-恶二唑环在同一分子中建立。显示了 3-oxopyridazine 和 5-thioxo-1,3,4-oxadiazole 环的互变异构结构以及它们的烷基化位置。在初步筛选时，合成的化合物显示出显着的植物生长刺激活性。选择最活跃的化合物进行更深入的研究和进一步的现场试验。