1-(异喹啉基)-2-萘胺 | 664302-70-9

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 1-(异喹啉基)-2-萘胺
• 中文别名: 1-(2-氨基-1-萘基)异喹啉
• 英文名称: 1-(2-amino-1-naphthyl)isoquinoline
• 英文别名: 1-(isoquinolin-1-yl)naphthalen-2-amine；1-isoquinolin-1-ylnaphthalen-2-amine
• CAS: 664302-70-9
• 化学式: C₁₉H₁₄N₂
• 分子量: 270.334
• InChiKey: OYLNFFGFQUEPML-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  454.2±30.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

SDS

1-(2-Amino-1-naphthyl)isoquinoline
SAFETY DATA SHEET

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Section 1. IDENTIFICATION OF THE SUBSTANCE OR MIXTURE AND OF THE SUPPLIER
Product name: 1-(2-Amino-1-naphthyl)isoquinoline

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
Pictograms or hazard symbols
Signal word Warning
Hazard statement Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): 1-(2-Amino-1-naphthyl)isoquinoline
Percent: >98.0%(T)
CAS Number: 664302-70-9
Synonyms: 1-(Isoquinolinyl)-2-naphthylamine
Chemical Formula: C19H14N2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1-(2-Amino-1-naphthyl)isoquinoline

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: crystal - powder
Color: White - Pale yellow
Odor: No data available
pH: No data available
1-(2-Amino-1-naphthyl)isoquinoline

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Melting point/freezing point:No data available
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
No data available
Upper:
Density: No data available
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not Listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
1-(2-Amino-1-naphthyl)isoquinoline

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 1-(异喹啉基)-2-萘胺 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到(E)-2-(((1-(isoquinolin-1-yl)naphthalen-2-yl)imino)methyl)-4-methoxyphenol
  参考文献：
  名称：

  具有萘基-异喹啉基团的N-水杨亚基苯胺衍生物的晶体结构和热致变色和荧光性质

  摘要：

  摘要 N-水杨基苯胺（SA）是一种经典的有机铬化合物，在光照射下表现出光致变色，在冷却时表现出热致变色。在本文中，我报告了新型 SA 衍生物 N-salicylidene-1-isoquinoline-2-naphthylamine (SN1-4) 的合成及其晶体结构和光致变色、热致变色和发光特性。尽管取代基不同，晶体中SN1-4的分子构象非常相似。由于 H…H 位阻排斥，萘环和异喹啉环在很大程度上相互扭曲。相比之下，苯酚和萘基环共面，二面角小于 10°。平面分子构象在这些衍生物中诱导了热致变色特性，并且还使它们非光致变色。而且，

  DOI：

  10.1016/j.molstruc.2020.129603
• 作为产物：
  描述：

  1-isoquinolin-1-yl-N-[(1S)-1-phenylethyl]naphthalen-2-amine 在 aluminum tri-bromide 、 乙硫醇 、 水 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到1-(异喹啉基)-2-萘胺
  参考文献：
  名称：

  对映体富集的轴向手性β-二酮亚胺的制备：（-）-和（+）-IAN胺的合成。

  摘要：

  描述了由异喹啉和2-氨基萘（IAN胺）组成的对映体富集的β-二酮亚胺的制备，从而为合成基于非外消旋的β-二酮亚胺和吡啶的手性催化剂提供了新的机会。

  DOI：

  10.1021/ol800728b

文献信息

• Synthesis of IAN-type N,N-Ligands via Dynamic Kinetic Asymmetric Buchwald–Hartwig Amination
  作者：Pedro Ramírez-López、Abel Ros、Antonio Romero-Arenas、Javier Iglesias-Sigüenza、Rosario Fernández、José M. Lassaletta

  DOI：10.1021/jacs.6b07972

  日期：2016.9.21

  nonaflates with aryl/alkyl primary amines using QUINAP as the ligand provides the corresponding axially chiral heterobiaryl amines with excellent yields and enantioselectivities. Reactivity and structural studies of neutral and cationic oxidative addition intermediates support a dynamic kinetic asymmetric amination mechanism based on the labilization of the stereogenic axis in the latter and suggest that

  使用 QUINAP 作为配体，Pd(0) 催化的外消旋杂二芳基溴化物、三氟甲磺酸酯或九氟甲磺酸酯与芳基/烷基伯胺的偶联提供了相应的轴向手性杂二芳基胺，具有优异的产率和对映选择性。中性和阳离子氧化加成中间体的反应性和结构研究支持基于后者立体轴不稳定的动态动力学不对称胺化机制，并表明胺与 Pd 中心的配位是立体决定步骤。
• Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
  作者：Aniruddha Biswas、Subarna Pan、Rajarshi Samanta

  DOI：10.1021/acs.orglett.2c00127

  日期：2022.3.4

  was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods

  开发了一种有效且直接的方法，用于在廉价的 Cu(II) 催化下使用容易获得的N-氧化物和重氮萘醌合成杂二芳基化合物。所开发的方法以简单的方式提供了 QUINOX 和相关同类物。以高位点选择性实现了范围广泛的重要杂二芳基化合物。合成的萘酚被转化为特权相关的 P,N 配体。合适的拆分方法可以直接提供相应的轴向手性杂二芳基化合物。
• A Preparation of Enantiomerically Enriched Axially Chiral β-Diketimines: Synthesis of (−)- and (+)-IAN Amine
  作者：Sarah B. Luesse、Carla M. Counceller、Jeremy C. Wilt、Brittany R. Perkins、Jeffrey N. Johnston

  DOI：10.1021/ol800728b

  日期：2008.6.1

  The preparation of an enantiomerically enriched beta-diketimine composed of isoquinoline and 2-aminonaphthalene (IAN amine) is described, thereby offering new opportunities in the synthesis of nonracemic beta-diketimine- and pyridine-based chiral catalysts.

  描述了由异喹啉和2-氨基萘（IAN胺）组成的对映体富集的β-二酮亚胺的制备，从而为合成基于非外消旋的β-二酮亚胺和吡啶的手性催化剂提供了新的机会。
• Crystal structures and thermochromic and fluorescence properties of N-salicylideneaniline derivatives having a naphthyl-isoquinoline group
  作者：Haruki Sugiyama

  DOI：10.1016/j.molstruc.2020.129603

  日期：2021.4

  thermochromism upon cooling. In this paper, I report the synthesis of novel SA derivatives, N-salicylidene-1-isoquinoline-2-naphthylamine (SN1-4), and their crystal structures and photochromic, thermochromic, and luminescence properties. The molecular conformations of SN1-4 in the crystals were very similar despite the different substituent groups. The naphthalene and isoquinoline rings were largely twisted

  摘要 N-水杨基苯胺（SA）是一种经典的有机铬化合物，在光照射下表现出光致变色，在冷却时表现出热致变色。在本文中，我报告了新型 SA 衍生物 N-salicylidene-1-isoquinoline-2-naphthylamine (SN1-4) 的合成及其晶体结构和光致变色、热致变色和发光特性。尽管取代基不同，晶体中SN1-4的分子构象非常相似。由于 H…H 位阻排斥，萘环和异喹啉环在很大程度上相互扭曲。相比之下，苯酚和萘基环共面，二面角小于 10°。平面分子构象在这些衍生物中诱导了热致变色特性，并且还使它们非光致变色。而且，