8-hydrazino-quinoline dihydrochloride | 91004-61-4

• 物质功能分类: 有机原料 - 肼或胲的有机衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-hydrazino-quinoline dihydrochloride
• 英文别名: 8-hydrazinoquinoline dihydrochloride；8-quinolylhydrazine dihydrochloride；8-hydrazino-quinoline; dihydrochloride；2-(Quinolin-8-yl)hydrazin-1-ium chloride；quinolin-1-ium-8-ylhydrazine;chloride
• CAS: 91004-61-4
• 化学式: C₉H₉N₃*2ClH
• 分子量: 232.112
• InChiKey: IBUQWIREEMZFJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  13
• 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：
  50.9
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Hydrazinoquinoline DiHCl
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: 8-Hydrazinoquinoline DiHCl
CAS number: 91004-61-4

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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, 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: C9H9N3.2ClH
Molecular weight: 232.1

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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：

  8-hydrazino-quinoline dihydrochloride 在 palladium on activated charcoal 硫酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.75h， 生成 11H-pyrido[2,3-a]carbazole
  参考文献：
  名称：

  Synthesis of 11H-pyridocarbazoles and derivatives. Comparison of their DNA binding and antitumor activity with those of 6H- and 7H-pyridocarbazoles

  摘要：

  The 8-methoxy- and 8-hydroxy-11H-pyrido[2,3-a]-, -[3,4-a]-, -[4,3-a]-, and [3,2-a]carbazoles were synthesized as potential DNA intercalating antitumor drugs. The structure of these compounds was confirmed by 1H NMR study including NOE experiments. The DNA binding properties of substituted and unsubstituted (8-H) heterocycles were determined by using their hydrochlorides or methiodides. These derivatives are able to bind to DNA with an affinity varying from 2.0 X 10(4) to 1.0 X 10(6) M-1, but most of them are unable to intercalate in contrast with the behavior of 6H- and 7H-pyridocarbazole analogues. The cytotoxicity of 11H-pyridocarbazoles, measured on L1210 cells in vitro, is much lower than those of 6H- and 7H-pyridocarbazole analogues.

  DOI：

  10.1021/jm00159a028

文献信息

• The synthesis of 4-(3,3-dimethyl-3<i>H</i>-pyrrolo[2,3-<i>f</i>]quinolin-2-yl)pyrazoles and 4-(3,3-dimethyl-3<i>H</i>-pyrrolo[3,2-<i>h</i>]quinolin-2-yl)pyrazoles
  作者：A. Rashidi、A. Afghan、Mehdi M. Baradarani、John A. Joule

  DOI：10.1002/jhet.18

  日期：2009.5

  3-methyl-butan-2-one into pyrido-indolenines 2,3,3-trimethyl-3H-pyrrolo[2,3-f]quinoline and 2,3,3-trimethyl-3H-pyrrolo[3,2-h]quinoline , respectively. Exposure of the indolenines to the Vilsmeier reagent produced aminomethylene-malondialdehydes and , which reacted with hydrazine or arylhydrazines to give 4-(3H-pyrrolo[2,3-f]quinolin-2-yl)- and 4-(3H-pyrrolo[3,2-h]quinolin-2-yl)-pyrazoles, and . J. Heterocyclic

  5-羟基喹啉和通过Fischer合成将8-肼基喹啉转化为3-甲基丁烷-2-酮成吡啶吲哚2,3,3-三甲基-3 H-吡咯并[2,3- f ]喹啉 和 2,3,3-三甲基-3 H-吡咯并[3,2- h ]喹啉 ， 分别。将吲哚肾上腺素暴露于Vilsmeier试剂产生的氨基亚甲基-丙二醛 和 ，其与肼或芳基肼反应，得到4-（3 H-吡咯并[2,3 - f ]喹啉-2-基）-和4-（3 H-吡咯并[3,2 - h ]喹啉-2-基）-吡唑类 和 。J. Heterocyclic Chem。，46，428（2009）。
• 2,6-Diformyl-4-tert-butylphenol bis(8-quinolylhydrazone) and its transition metal complexes: Physicochemical study and quantum-chemical simulation
  作者：L. D. Popov、S. I. Levchenkov、I. N. Shcherbakov、Yu. P. Tupolova、V. A. Kogan

  DOI：10.1134/s1070363208010167

  日期：2008.1

  2,6-Diformyl-4-tert-butylphenol bis(8-quinolylhydrazone) and its transition metal complexes of the compositions [Cu2(H2L)Cl]Cl2, [Ni2(H2L)Cl3], and [Mn2(H2L)Cl3], where H2L is the monodeprotonated form of the hydrazone, are prepared. The conformations of the bis-hydrazone, geometries of the complexes, and parameters of exchange coupling between the ferromagnetic centers are evaluated by quantum-chemical calculations. The calculation results are compared with the results of the physicochemical study of the compounds. Factors affecting the stability of various forms of the ligand and complexes are discussed.

  制备了2,6-二醛基-4-叔丁基苯酚双（8-喹啉腙）及其过渡金属配合物[Cu2(H2L)Cl]Cl2、[Ni2(H2L)Cl3]和[Mn2(H2L)Cl3]，其中H2L是腙的单质子化形式。通过量子化学计算评估了双腙的构象、配合物的几何形状以及铁磁中心之间的交换偶合参数。将计算结果与化合物的物理化学研究结果进行了比较。讨论了影响配体和配合物各种形式稳定性的因素。
• Grazia Ferlin; Chiarelotto; Baccichetti, Il Farmaco, 1992, vol. 47, # 12, p. 1513 - 1528
  作者：Grazia Ferlin、Chiarelotto、Baccichetti、Carlassare、Toniolo、Bordin

  DOI：——

  日期：——
• Buu-Hoi,N.P.; Saint-Ruf,G., Israel Journal of Chemistry, 1963, vol. 1, p. 369 - 373
  作者：Buu-Hoi,N.P.、Saint-Ruf,G.

  DOI：——

  日期：——
• Protolytic properties of 8-quinolylhydrazones of substituted salicylaldehydes and physicochemical properties of their copper(II) complexes
  作者：L. D. Popov、S. I. Levchenkov、I. N. Shcherbakov、V. A. Kogan

  DOI：10.1134/s1070363207070225

  日期：2007.7

  Acid-base properties of hydrazones derived from 8-hydrazinoquinoline and substituted salicylaldehydes were studied. Under the experimental conditions, only the first step of ionization of the hydrazones is realized. The ionization constants were calculated quantum-chemically. Copper(II) complexes of these hydrazones, (HL)Cu(X)(CH3OH)(n), were isolated (HL- is the monodeprotonated form of hydrazones, and X- is the acid residue). According to the data of elemental analysis, IR spectroscopy, conductometry, and magnetochemistry, the majority of the complexes have a binuclear structure. The copper(II) ions in the dimeric complex show antiferromagnetic exchange coupling. The ionization constants of the hydrazones and the exchange parameters strongly depend on the substituent in the salicylaldehyde moiety.