2-氨基-8-羟基喹啉 | 70125-16-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 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-氨基-8-羟基喹啉
• 中文别名: 2-氨基-8-喹啉醇
• 英文名称: 2-amino-8-quinolinol
• 英文别名: 2-amino-8-hydroxyquinoline；2-aminoquinolin-8-ol；8-hydroxy-2-aminoquinoline；8-hydroxy-quinolin-2-ylamine
• CAS: 70125-16-5
• 化学式: C₉H₈N₂O
• mdl: MFCD00168931
• 分子量: 160.175
• InChiKey: UFVLIVCXTIGACT-UHFFFAOYSA-N

物化性质

• 熔点：
  157-160 °C
• 溶解度：
  可溶于丙酮、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 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

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Amino-8-quinolinol
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. : 70125-16-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
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
Xi Irritant R36/37/38
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 Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
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
Synonyms : 2-Amino-8-hydroxyquinoline
Formula : C9H8N2O
Molecular Weight : 160,17 g/mol
CAS-No. : 70125-16-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Amino-8-quinolinol
CAS-No. 70125-16-5 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Amino-8-quinolinol
CAS-No. 70125-16-5 Xi, R36/37/38 <= 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
Carbon oxides, nitrogen oxides (NOx)
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.Normal measures for preventive fire
protection.
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)
A part 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
Safety glasses with side-shields conforming to EN166 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.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone] test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: crystalline
Colour: light brown
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 157 - 160 °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- no data available
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
no data available
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available

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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. Contact a licensed
professional waste disposal service to dispose of this material. 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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
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
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

用途

2-氨基-8-羟基喹啉是一种喹啉类衍生物，主要用于制备络合剂，并广泛应用于有机合成和制药工业。

反应信息

• 作为反应物：
  描述：

  2-氨基-8-羟基喹啉 在 PS-PPh3 、 cyanoborane 、 偶氮二甲酸二苄酯 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 8-(((3R)-1-benzylpyrrolidin-3-yl)oxy)quinolin-2-amine
  参考文献：
  名称：

  合成和评估2-氨基-8-烷氧基喹啉作为MCHr1拮抗剂。第三部分

  摘要：

  先前对2-氨基-8-烷氧基喹啉MCHr1拮抗剂的SAR研究表明，具有无环酰胺基侧链的化合物显示出优异的结合力和功能效能，但CNS渗透率可忽略不计。具有无环苄基胺侧链的相关类似物显示大大改善了中枢神经系统的暴露，但功能效力受到影响。在这份报告中，我们证明了这些苄基胺侧链的环化作用提供了结合了这类拮抗剂中效价和CNS渗透力最佳元素的化合物。化合物21举例说明了这一点，该化合物具有亚纳摩尔级的MCHr1结合亲和力，良好的功能效能和24小时内出色的CNS暴露。

  DOI：

  10.1016/j.bmcl.2004.07.035
• 作为产物：
  描述：

  8-羟基喹啉-N-氧化物 在 硫酸二甲酯 、 氨 作用下， 以 乙腈 、 水 为溶剂， 反应 3.25h， 以47%的产率得到2-氨基-8-羟基喹啉
  参考文献：
  名称：

  2-氨基-8-羟基喹啉的首次安全实用合成

  摘要：

  描述了重要结构单元 2-氨基-8-羟基喹啉 (1) 的首次安全有效合成。从廉价的大宗化学品 8-羟基喹啉 (2) 中容易获得的 N-氧化物 3 开始，通过两步一锅法以良好的总收率 (53-66%) 和纯度 (>98%) 获得目标化合物) 在没有色谱的情况下以千克为单位。

  DOI：

  10.1021/op049944p

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING ZINC MATRIX METALLOPROTEASE DEPENDENT DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS PERMETTANT DE TRAITER DES MALADIES DÉPENDANT DE MÉTALLOPROTÉASES À ZINC MATRICIELLES
  申请人：ABSOLUTE SCIENCE INC

  公开号：WO2009045761A1

  公开（公告）日：2009-04-09

  The present invention provides compounds and methods for treating zinc matrix metalloprotease dependent diseases. In certain embodiments, the compounds of the present invention have the following formulas:

  本发明提供了用于治疗锌基质金属蛋白酶依赖性疾病的化合物和方法。在某些实施例中，本发明的化合物具有以下公式：
• Cathepsin B inhibitors: Further exploration of the nitroxoline core
  作者：Izidor Sosič、Ana Mitrović、Hrvoje Ćurić、Damijan Knez、Helena Brodnik Žugelj、Bogdan Štefane、Janko Kos、Stanislav Gobec

  DOI：10.1016/j.bmcl.2018.02.042

  日期：2018.4

  their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline

  人组织蛋白酶B是一种半胱氨酸蛋白酶，具有许多看家功能，例如溶酶体内的细胞内蛋白水解。它增加的活性和表达与包括癌症在内的许多病理过程密切相关。我们在这里介绍设计​​和合成作为组织蛋白酶B抑制剂的新的硝基氧代林衍生物。这些衍生物可通过省略吡啶部分或修饰硝基氧代林的2、7和8位来制备。评估了所有化合物抑制组织蛋白酶B的内肽酶和外肽酶活性的能力。对于最有希望的抑制剂，确定了减少细胞外和细胞内胶原IV降解的能力，然后在基于细胞的体外进行了评估肿瘤侵袭模型。所提供的数据表明，我们进一步确定了氮氧杂环丁烷衍生物抑制组织蛋白酶B的结构要求，并提供了可能导致非肽类化合物对抗肿瘤进展的其他知识。
• N-acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020055631A1

  公开（公告）日：2002-05-09

  N-Benzoyl arylsulfonamides having the formula 1 are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-Xl抑制剂，有助于促进细胞凋亡。还公开了BCL-Xl抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• N-Acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020086887A1

  公开（公告）日：2002-07-04

  N-Benzoyl arylsulfonamides having the formula 1 Are BCL-X1 inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-X1 inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-X1抑制剂，有助于促进细胞凋亡。还公开了BCL-X1抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• Synthesis, structural characterization and leishmanicidal activity evaluation of ferrocenyl N-heterocyclic compounds
  作者：Susana Quintal、Tânia S. Morais、Cristina P. Matos、M. Paula Robalo、M. Fátima M. Piedade、Maria J. Villa de Brito、M. Helena Garcia、Mónica Marques、Carla Maia、Lenea Campino、João Madureira

  DOI：10.1016/j.jorganchem.2013.07.044

  日期：2013.11

  against the human caucasian histiocytic lymphoma U-937 cell line was analyzed for the same set of compounds. All of them show activity against promastigote forms of L. infantum parasites at relatively high concentration (64–269 μM). Among the complexes that showed a better ratio between the toxic and the therapeutic dose, 3, 9 and 12 were selected for further studies in infected macrophages. Such compounds

  与通式FCC（O）L新二茂铁衍生物[FC =（η 5 -C 5 H ^ 5）的Fe（η 5 -C 5 H ^ 4）]，其中L是氨基喹啉或hydroxyaminoquinoline，已为评价合成它们的杀菌特性。设计这些化合物时，将二茂铁通过酰胺或酯桥与喹啉偶联。二茂铁基成分旨在在体内后充当喹啉载体和ROS生产者氧化成Fe（III），同时降低偶联喹啉的正常细胞毒性。选择桥是基于其已知的能力在吞噬溶酶体中被富含蛋白酶/酯酶的介质水解，噬菌体是细胞内利什曼原虫寄生虫的靶标。 新化合物包括N-（喹啉-3-基）二茂铁酰胺（4），N-（喹啉-5-基）二茂铁酰胺（5），N-（喹啉-6-基）二茂铁酰胺（6），N-（2 -甲基-喹啉-4-基）二茂铁酰胺（7），N-（2-甲基喹啉-6-基）二茂铁酰胺（8），N-（6-甲氧基喹啉-8-基）二茂铁酰胺（9），2-氨基-喹啉-8-二茂铁酸酯（10）和2-氨基喹啉-4-