7-氯-8-甲基喹啉 | 78941-93-2

• 物质功能分类: 化学农药原药 - 除草剂 - 除草剂中间体
• 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
• 中文名称: 7-氯-8-甲基喹啉
• 英文名称: 7-Chloro-8-methylquinoline
• CAS: 78941-93-2
• 化学式: C₁₀H₈ClN
• mdl: MFCD09743893
• 分子量: 177.633
• InChiKey: NKWDCLXGUJHNHS-UHFFFAOYSA-N

物化性质

• 熔点：
  45-48 °C
• 沸点：
  278 °C(Press: 759 Torr)
• 密度：
  1.225±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、二氯甲烷（少量）、乙酸乙酯（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Chloro-8-methylquinoline
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: 7-Chloro-8-methylquinoline
CAS number: 78941-93-2

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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: C10H8ClN
Molecular weight: 177.6

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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

制备方法与用途

化学性质
纯品为无色针状结晶，熔点48℃，沸点270℃/0.1Mpa，能溶解于乙醇、乙醚、丙酮、石油醚、苯和甲苯等有机溶剂中，而不溶于水。工业品则呈现米黄色固体状态，熔点在40～42℃之间，相对密度为1.15，含量通常在94%以上。

用途
7-氯-8-甲基喹啉是除草剂二氯喹啉酸的关键中间体。

生产方法
其制备过程是在反应釜中依次加入水、硫酸、3-氯-2-甲基苯胺和碘化钠，随后在负压条件下加热并升温。之后，分批缓慢添加甘油，并持续脱水及用碱液吸收生成的二氧化硫。完成反应后，转移至装有冷水的中和釜内降温，加入溶剂油，并使用氢氧化钠溶液进行中和、过滤与静置分离。最后，从油层中去除溶剂以获得成品。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-氯-8-甲基喹啉	5-chloro-8-methylquinoline	78941-95-4	C10H8ClN	177.633
  8-甲基喹啉	8-methylquinoline	611-32-5	C10H9N	143.188

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	7-Chloro-8-bromomethylquinoline	84163-79-1	C10H7BrClN	256.529
  ——	3,7-dichloro-8-chloromethylquinoline	84086-96-4	C10H6Cl3N	246.523
  3,7-二氯-8-(二氯甲基)喹啉	3,7-dichloro-8-dichloromethylquinoline	84086-97-5	C10H5Cl4N	280.968
  7-氯-8-喹啉羧酸	7-chloro-8-quinolinecarboxylic acid	87293-44-5	C10H6ClNO2	207.616
  8-乙基喹啉	8-ethylquinoline	19655-56-2	C11H11N	157.215
  ——	8-pentylquinoline	——	C14H17N	199.296
  7-氨基-8-甲基喹啉	7-amino-8-methylquinoline	116632-62-3	C10H10N2	158.203

反应信息

• 作为反应物：
  描述：

  7-氯-8-甲基喹啉 在 N-氯代丁二酰亚胺 、 palladium diacetate 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以70%的产率得到7-chloro-8-(nitromethyl)quinoline
  参考文献：
  名称：

  一种合成8-(硝基甲基)喹啉类化合物的方法

  摘要：

  本发明提供了一种合成8‑(硝基甲基)喹啉类化合物的方法：以8‑甲基喹啉类化合物为原料，与催化剂和硝化试剂加入有机溶剂中，密闭加热至80‑130℃反应，TLC跟踪至反应结束后，反应液后处理制得式II所示的8‑(硝基甲基)喹啉类化合物。本发明的硝化方法具有硝化位置专一性的优点，只在甲基上硝化，而没有苯环上硝化产物的生成，反应过程安全环保、底物适应性好，各种取代基都可以实现甲基硝化；直接以8‑甲基喹啉为原料，反应步骤简单，是一种合成各种含取代基的8‑(硝基甲基)喹啉类化合物的新路线。

  公开号：

  CN104860880B
• 作为产物：
  描述：

  8-甲基喹啉 在 silver sulfate 氯 作用下， 以 硫酸 为溶剂， 反应 56.0h， 生成 7-氯-8-甲基喹啉
  参考文献：
  名称：

  8-甲基喹啉的芳族氯化和碘化。5-卤代8-甲基喹啉的苄基溴化

  摘要：

  DOI：

  10.1007/bf00505763

文献信息

• Ru(<scp>ii</scp>)-catalyzed amidation reactions of 8-methylquinolines with azides via C(sp³)–H activation
  作者：Bingxian Liu、Bin Li、Baiquan Wang

  DOI：10.1039/c5cc06230f

  日期：——

  The Ru(II)-catalyzed amidation reactions of 8-methylquinolines with azides have been developed. It is the first example of [(p-cymene)RuCl2]2-catalyzed C(sp3)-H bond intermolecular amidation reaction which give quinolin-8-ylmethanamines under mild reaction conditions...

  已经开发了Ru（II）催化的8-甲基喹啉与叠氮化物的酰胺化反应。这是[（对-异丙基）RuCl2] 2-催化的C（sp3）-H键分子间酰胺化反应的第一个例子，该反应在温和的反应条件下产生了喹啉-8-基甲胺。
• Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
  作者：Shanghua Xia、Lu Gan、Kailiang Wang、Zheng Li、Dawei Ma

  DOI：10.1021/jacs.6b08114

  日期：2016.10.19

  powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively

  Cu(acac)2 和 N,N'-双(4-羟基-2,6-二甲基苯基)草酰胺 (BHMPO) 的组合为（杂）芳基卤化物的羟基化提供了强大的催化系统。各种带有给电子或吸电子基团的（杂）芳基氯化物在 130 °C 下均能很好地进行，以良好到极好的产率提供相应的酚类和羟基化杂芳烃。当使用反应性更强的（杂）芳基溴化物和碘化物时，羟基化反应在相对较低的温度（分别为 80 和 60 °C）下在低催化负载（0.5 mol% Cu）下完成。
• Rh(<scp>iii</scp>)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds
  作者：Bidhan Ghosh、Rajarshi Samanta

  DOI：10.1039/c9cc02391g

  日期：——

  A straightforward Rh(III)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)–H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective

  开发了一种简单的Rh（III）催化的一般策略，即使用重氮萘-2（1 H）-ones /醌二叠氮化物将萘酚/苯酚部分引入8-甲基喹啉的C（sp 3）-H键。所开发的方法进一步扩展到8-甲酰基喹啉的芳基化反应，以完成二芳基酮衍生物。该方法简单，相对快速，并且具有广泛的范围和功能基团耐受性，具有化学和区域选择性。通过克规模的合成和生物活性分子的建设建立了合成实用程序。
• Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C–H Activation
  作者：Yuqin Jiang、Pengfei Li、Jie Zhao、Bingxian Liu、Xingwei Li

  DOI：10.1021/acs.orglett.0c02618

  日期：2020.10.2

  The rhodium(III)-catalyzed coupling of C–H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C–H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol

  铑（III）催化的C–H底物与碘鎓碘化物的偶联已经实现了各种环状骨架的有效合成，其中碘鎓碘化物已被认为是有效且出色的卡宾前体。该反应系统适用于在轻度和氧化还原中性条件下的sp 2和sp 3 C–H底物。在克规模的反应中，催化剂的负载量可以低至0.5mol％。代表性产品在纳摩尔水平下对人癌细胞具有细胞毒性。
• Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp³)−H and C(sp²)−H under Rhodium(III) Catalysis
  作者：Songjie Yu、Guodong Tang、Yingzi Li、Xukai Zhou、Yu Lan、Xingwei Li

  DOI：10.1002/anie.201602224

  日期：2016.7.18

  nitrogenation suffered from simple amidation/amination with limited atom‐economy and is mostly limited to C(sp2)−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp2)−H and C(sp3)−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the

  以前的直接CH H氮化反应受简单的酰胺化/胺化作用和原子经济的限制，并且大多限于C（sp 2）-H底物。在这项工作中，将蒽醌设计为在铑（III）催化下同时用于C（sp 2）-H和C（sp 3）-H键的新型双功能胺化试剂，从而提供了拴接到亲电羰基的亲核苯胺。已经分离出三登酸盐铑（III）配合物作为催化剂的静止状态，DFT研究确定了亚硝基物质的中间体。