2-氯-6-甲氧基喹啉 | 13676-02-3

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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
• 中文名称: 2-氯-6-甲氧基喹啉
• 英文名称: 2-chloro-6-methoxyquinoline
• CAS: 13676-02-3
• 化学式: C₁₀H₈ClNO
• mdl: MFCD00799212
• 分子量: 193.633
• InChiKey: ZFEJTYQUWRVCFW-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107℃
• 沸点：
  310.5±22.0 °C(Predicted)
• 密度：
  1.267

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R41
• WGK Germany：
  3
• 海关编码：
  2933499090
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H318
• 危险性防范说明：
  P280,P305 + P351 + P338
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Chloro-6-methoxyquinoline
: BBO000233
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 13676-02-3

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Serious eye damage (Category 1), H318
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R41
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Harmful if swallowed.
Causes serious eye damage.
Precautionary statement(s)
Wear protective gloves/ eye protection/ face protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C10H8ClNO
Molecular Weight : 193,63 g/mol
CAS-No. : 13676-02-3
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Chloro-6-methoxyquinoline
CAS-No. 13676-02-3 Acute Tox. 4; Eye Dam. 1; <= 100 %
H302, H318
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Chloro-6-methoxyquinoline
CAS-No. 13676-02-3 Xn, R22 - R41 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 108 - 109 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,975
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
R41 Risk of serious damage to eyes.
Further information
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氯-6-甲氧基喹啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 DEGME 、 水 为溶剂， 反应 3.0h， 生成 3-氯-4-(6-羟基喹啉-2-基)苯甲酸
  参考文献：
  名称：

  [EN] NOVEL SUBSTITUTED BICYCLIC AROMATIC COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
  [FR] NOUVEAUX COMPOSÉS AROMATIQUES BICYCLIQUES SUBSTITUÉS EN TANT QU'INHIBITEURS DE LA S-NITROSOGLUTATHION RÉDUCTASE

  摘要：

  本发明涉及一类新颖的取代双环芳族化合物，该化合物可用作S-硝基谷胱甘肽还原酶（GSNOR）的抑制剂，包括含有此类化合物的药物组合物，以及制造和使用这些化合物的方法。

  公开号：

  WO2012083165A1
• 作为产物：
  描述：

  6-甲氧基喹啉 在 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-氯-6-甲氧基喹啉
  参考文献：
  名称：

  发现新的基于喹诺酮的二芳基酰胺作为有效的 B-RAFV600E/C-RAF 激酶抑制剂，具有良好的体外抗癌活性。

  摘要：

  癌症对靶向治疗的耐药性的出现代表了癌症治疗中的重大挑战。因此，确定新的抗癌候选物，特别是那些针对致癌突变体的候选物，是一项紧迫的医疗需求。已经进行了结构修饰运动以进一步优化我们之前报道的 2-苯胺喹啉-二芳基酰胺缀合物 VII 作为 B-RAFV600E/C-RAF 抑制剂。考虑到在末端苯基和环状二胺之间加入亚甲基桥，已经对基于喹啉的芳基酰胺进行了定制、合成和生物学评估。其中，5/6-羟基喹啉 17b 和 18a 作为最有效的成员脱颖而出，IC50 值为 0.128 µM，针对 B-RAFV600E 为 0.114 µM，针对 C-RAF 为 0.0653 µM，0.0676 µM。最重要的是，17b 对临床耐药的 B-RAFV600K 突变体具有显着的抑制效力，IC50 值为 0.0616 µM。通过分子对接和分子动力学 (MD) 研究了 17b 和 18a 的假定结合模式。此外，所有目标化合物的抗增殖活性已通过一组

  DOI：

  10.3390/ijms24043216

文献信息

• Candidate PET Radioligand Development for Neurofibrillary Tangles: Two Distinct Radioligand Binding Sites Identified in Postmortem Alzheimer’s Disease Brain
  作者：Lisheng Cai、Baoxi Qu、Bryan T. Hurtle、Sureshbabu Dadiboyena、Ramon Diaz-Arrastia、Victor W. Pike

  DOI：10.1021/acschemneuro.6b00051

  日期：2016.7.20

  [(18)F]THK-523 and [(18)F]807 are promising radioligands for imaging neurofibrillary tangles (NFTs) with positron emission tomography (PET) in neurodegenerative diseases, such as Alzheimer's disease (AD) and traumatic brain injury. Although [(18)F]THK-523 and [(18)F]T807 are considered high-affinity selective radioligands for NFTs, uncertainty has existed as to whether PET radioligands for imaging

  [（18）F] THK-523和[（18F）] 807是有前途的放射性配体，可用于在神经退行性疾病（例如阿尔茨海默氏病（AD）和颅脑损伤）中用正电子发射断层扫描（PET）成像神经原纤维缠结（NFT）。尽管[（18）F] THK-523和[（18）F] T807被认为是NFT的高亲和选择性放射性配体，但用于成像NFT的PET放射性配体是否结合同一分子位点仍存在不确定性，因为体外检测缺乏与NFT结合的配体。我们用tri标记了THK-523和T807，以作为参考放射性配体用于体外结合试验，其中AD脑匀浆用于新合成的配体。使用这些放射性配体，我们确定了两个不同的小分子结合位点，一个位点对THK-523具有高亲和力，另一个位点对T807具有高亲和力。此外，[（3）H] PIB的结合测定证实，这两个新发现的结合位点也不同于硫黄素-T结合位点，在该位点上，用于成像β-淀粉样蛋白斑的所有当前临床上有用的P
• Regioselective Chlorination of Quinoline<i>N</i>-Oxides and Isoquinoline<i>N</i>-Oxides Using PPh₃/Cl₃CCN
  作者：Kai Qiao、Li Wan、Xiaoning Sun、Kai Zhang、Ning Zhu、Xin Li、Kai Guo

  DOI：10.1002/ejoc.201501567

  日期：2016.3

  A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition,

  已经开发了一种用于杂环 N-氧化物的区域选择性 C2-氯化的新方法。以PPh3/Cl3CCN为氯化试剂，以令人满意的收率顺利地获得了所需的N-杂环氯化物。反应以高效和选择性的方式在广泛的底物上进行，表现出优异的官能团耐受性。此外，该氯化反应可用于修饰有吸引力的配体和药物的 N-杂环支架。
• [EN] SOLID FORMS OF AN S-NITROSOGLUTATHIONE REDUCTASE INHIBITOR<br/>[FR] FORMES SOLIDES D'UN INHIBITEUR DE S-NITROSOGLUTATHIONE RÉDUCTASE
  申请人：NIVALIS THERAPEUTICS INC

  公开号：WO2017044766A1

  公开（公告）日：2017-03-16

  The present invention provides solid forms and compositions thereof, which are useful as an inhibitor of S-nitrosoglutathione reductase and which exhibit desirable characteristics for the same.

  本发明提供了固体形态及其组合物，它们可用作S-亚硝基谷胱甘肽还原酶的抑制剂，并展现出对此目的所需的有益特性。
• TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE
  申请人：Hutchinson John Howard

  公开号：US20070173508A1

  公开（公告）日：2007-07-26

  Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.

  本文描述了含有这些化合物的化合物和药物组合物，这些化合物抑制5-脂氧合酶（5-LO）的活性。本文还描述了使用这种5-LO抑制剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他依赖或介导白三烯的状况、疾病或紊乱。
• Imaging agents for detecting neurological disorders
  申请人：Gangadharmath Umesh B.

  公开号：US20100239496A1

  公开（公告）日：2010-09-23

  Imaging agents of formula (I) and methods for detecting neurological disorders comprising administering to a patient in need compounds of formula (I) capable of binding to tau proteins and β-amyloid peptides are presented herein. The invention also relates to methods of imaging Aβ and tau aggregates comprising introducing a detectable quantity of pharmaceutical formulation comprising a radiolabeled compound of formula (I) and detecting the labeled compound associated with amyloid deposits and/or tau proteins in a patient. These methods and compositions enable preclinical diagnosis and monitoring progression of AD and other neurological disorders.

  本文提供了一种公式（I）的成像剂和检测神经系统疾病的方法，包括向需要的患者施用能够结合tau蛋白和β-淀粉样肽的公式（I）化合物。该发明还涉及成像Aβ和tau聚集物的方法，包括引入含有公式（I）放射标记化合物的制剂的可检测量，并检测与淀粉样沉积物和/或tau蛋白相关的标记化合物在患者体内的情况。这些方法和组合物使得能够进行临床前诊断和监测阿尔茨海默病和其他神经系统疾病的进展。