1-溴-2-萘甲醛 | 3378-82-3

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-溴-2-萘甲醛
• 中文别名: 1-溴-2-萘醛
• 英文名称: 1-bromo-2-naphthaldehyde
• 英文别名: 1-bromonaphthalene-2-carbaldehyde；1-bromo-2-formylnaphthalene；1-bromo-2-naphthalenecarboxaldehyde
• CAS: 3378-82-3
• 化学式: C₁₁H₇BrO
• 分子量: 235.08
• InChiKey: CYGUXEZVBLMVRV-UHFFFAOYSA-N

物化性质

• 熔点：
  118°C
• 沸点：
  347℃
• 密度：
  1.552
• 闪点：
  120℃
• 溶解度：
  溶于甲醇
• 稳定性/保质期：

  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8℃，避光、通风干燥处，密封保存。

SDS

1-Bromo-2-naphthaldehyde Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 1-Bromo-2-naphthaldehyde

Revision number: 1

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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-Bromo-2-naphthaldehyde
Percent: >96.0%(GC)
CAS Number: 3378-82-3
Chemical Formula: C11H7BrO

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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.
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.
1-Bromo-2-naphthaldehyde

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Section 4. FIRST AID MEASURES
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.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
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 under inert gas.
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
Solid
Physical state (20°C):
Form: crystal - powder
Color: Very pale yellow - Pale yellow
Odor: No data available
pH: No data available
Melting point/freezing point:118 °C
1-Bromo-2-naphthaldehyde

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
No data available
Lower:
Upper: No data available
No data available
Density:
Solubility: Soluble in : Methanol

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Conditions to avoid: Air-sensitive
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
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-Bromo-2-naphthaldehyde

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-溴-2-萘甲醛 在 potassium permanganate 、 溴 、 铁粉 、 铜 作用下， 以 四氯化碳 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.34h， 生成 dimethyl 1,1'-bis(4-bromo-2-naphthoate)
  参考文献：
  名称：

  三重 Diels-Alder 反应的对映选择性催化：范围和机制研究

  摘要：

  手性敏化剂 1,1'-双（2,4-二氰基萘）和 1,1'-双（2,10-二氰基蒽）的辐照催化反式-β-甲基苯乙烯与 1,3-环己二烯形成[4+2]环加合物endo-trans-6-methyl-5-phenylbicyclo[2.2.2]oct-2-ene。当敏化剂具有光学活性并在乙醚或甲苯溶液中低温照射时，对映选择性形成[4+2]环加合物

  DOI：

  10.1021/ja00050a011
• 作为产物：
  描述：

  2-甲基萘 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 N₄(CH₂)6 、 溴 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 二硫化碳 、 四氯化碳 为溶剂， 反应 3.0h， 生成 1-溴-2-萘甲醛
  参考文献：
  名称：

  一种新颖的包合物设计：通过联萘铰链和附加的配位基团选择性地包含不带电的分子。1,1'-联萘-2,2'-二羧酸主体/羟基客体包裹体的X射线晶体结构和结合模式

  摘要：

  Etude de cinq clathrates du compose du titre (1) avec des alcools differents: 1.2 MeOH (P2 1 /n, Z=4), 1.2 EtOH (C2/c, Z=4), 1.2 (PrOH-2) (C2/ c, Z=4), 1.(RuOH-2) (P2 1 /n, Z=4), 1.乙二醇(P2 1 /n, Z=4)。关系

  DOI：

  10.1021/ja00323a039

文献信息

• Carbonyl-Directed Addition of <i>N</i>-Alkylhydroxylamines to Unactivated Alkynes: Regio- and Stereoselective Synthesis of Ketonitrones
  作者：Yilin Liu、Xiangqing Feng、Yanyun Liu、Hongwei Lin、Yuanxiang Li、Yingying Gong、Lei Cao、Liping Chen

  DOI：10.1021/acs.orglett.8b03522

  日期：2019.1.18

  A variety of ketonitrones were synthesized in moderate to excellent yields with high chemo-, regio-, and stereoselectivity by using carbonyl-directed addition of N-alkylhydroxylamines to unactivated alkynes under mild conditions. The product diverisity could be controlled by the use of different bases, and EtN(n-Pr)2 could promote the formation of ketonitrones while using EtONa as base led to indanone-derived

  通过在温和的条件下使用N-烷基羟胺的羰基定向加成反应，以中等至优异的产率合成了多种酮硝基酮，具有较高的化学，区域和立体选择性。可以通过使用不同的碱来控制产物的剥离性，而以EtONa为碱生成茚满酮衍生的硝酮时，EtN（n -Pr ）2可以促进酮硝酮的形成。对照实验表明，除吸电子基团以外，底物的羰基起H键受体的作用，共轭烯酮骨架具有高选择性。
• Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
  作者：Mei-Ling Tan、Shuo Tong、Sheng-Kai Hou、Jingsong You、Mei-Xiang Wang

  DOI：10.1021/acs.orglett.0c01775

  日期：2020.7.17

  catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction

  我们在本文中报道了CuI / DMEDA催化酰胺与各种二（邻-溴芳基）甲烷的N，N-二芳基化反应，以产生各种9,10-二氢ac啶衍生物。在温和条件下选择性氧化所得的9,10-二氢ac啶衍生物，得到afford啶，a啶酮和a啶鎓衍生物。铜催化的N，N-二芳基化反应与氧化芳构化反应相结合，使得能够容易地构建具有不同邻位熔融模式的氮原子嵌入的四碳烯和并五碳烯。还证明了发光特性，特别是融合模式对获得的N-多态荧光发射的影响。
• Metal-free synthesis of imidazole by BF₃·Et₂O promoted denitrogenative transannulation of <i>N</i>-sulfonyl-1,2,3-triazole
  作者：Dongdong Yang、Lihong Shan、Ze-Feng Xu、Chuan-Ying Li

  DOI：10.1039/c8ob00083b

  日期：——

  BF3·Et2O promoted metal-free denitrogenative transannulation of N-sulfonyl-1,2,3-triazole was reported. Rather than transition metals, BF3·Et2O was employed for the first time to promote the formation of α-diazoimines from N-sulfonyl-1,2,3-triazoles in nitriles, leading to the synthesis of various imidazoles. The protocol tolerates a broad range of functional groups and could also be applied to the

  据报道，BF 3 ·Et 2 O促进了N-磺酰基-1，2，3-三唑的无金属脱氮脱环。首次使用BF 3 ·Et 2 O而不是过渡金属来促进腈中N-磺酰基-1,2,3-三唑形成α-重氮亚胺，从而合成了各种咪唑。该方案可耐受各种官能团，还可用于生物活性分子的后期修饰，证明了该方案在有机合成中的潜力。提出了一个合理的机制。
• HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
  作者：Sachin Handa、Martin P. Andersson、Fabrice Gallou、John Reilly、Bruce H. Lipshutz

  DOI：10.1002/anie.201510570

  日期：2016.4.11

  complexed in a 1:1 ratio with Pd(OAc)2, enables Pd‐catalyzed cross‐couplings to be run using ≤1000 ppm of this pre‐catalyst. Applications to Suzuki–Miyaura reactions involving highly funtionalized reaction partners are demonstrated, all run using environmentally benign nanoreactors in water at ambient temperatures. Comparisons with existing state‐of‐the‐art ligands and catalysts are discussed herein.

  新的单膦配体HandaPhos已被鉴定为，当与Pd（OAc）2以1：1的比例络合时，可使用≤1000ppm的这种预催化剂进行Pd催化的交叉偶联。展示了在涉及高度官能化反应伙伴的Suzuki–Miyaura反应中的应用，所有反应均使用环境友好的纳米反应器在环境温度下的水中进行。本文讨论了与现有最​​先进的配体和催化剂的比较。
• A Highly Active Suzuki Catalyst for the Synthesis of Sterically Hindered Biaryls:  Novel Ligand Coordination
  作者：Jingjun Yin、Matthew P. Rainka、Xiao-Xiang Zhang、Stephen L. Buchwald

  DOI：10.1021/ja017082r

  日期：2002.2.1

  A catalyst system for the preparation of biaryls containing four ortho substituents via Suzuki coupling is described. The combination of a catalytic quantity of Pd2(dba)3 with either an electron-rich biarylphosphine or DPEPhos is effective using a wide range of substrates. The X-ray crystal structure of (dba)Pd(2-(9-phenanthryl)phenyl-dicyclohexylphosphine), in which the Pd is coordinated to the 9

  描述了通过 Suzuki 偶联制备含有四个邻位取代基的联芳基的催化剂体系。催化量的 Pd2(dba)3 与富电子联芳膦或 DPEPhos 的组合使用广泛的底物是有效的。还报告了 (dba) Pd(2-(9-菲基)苯基-二环己基膦)的 X 射线晶体结构，其中 Pd 与菲基的 9,10-双键配位。

表征谱图