6-甲氧基-2-萘乙烯 | 63444-51-9

• 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 - 苯类化合物 - 萘
• 中文名称: 6-甲氧基-2-萘乙烯
• 中文别名: 6-甲氧基-2-乙烯基萘
• 英文名称: 2-methoxy-6-vinylnapthalene
• 英文别名: 2-methoxy-6-vinylnaphthalene；6-methoxy-2-vinylnaphthalene；2-vinyl-6-methoxynaphthalene；2-ethenyl-6-methoxynaphthalene；1-(6-methoxy-2-naphthyl)ethene
• CAS: 63444-51-9
• 化学式: C₁₃H₁₂O
• 分子量: 184.238
• InChiKey: DGQUMYDUFBBKPK-UHFFFAOYSA-N

物化性质

• 熔点：
  88-91 °C
• 沸点：
  278.19°C (rough estimate)
• 密度：
  1.0120 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2909309090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	6-Methoxy-2-Vinylnaphthalene Material Safety Data Sheet
Synonym:	None Known
CAS:	63444-51-9

Section 1 - Chemical Product MSDS Name:6-Methoxy-2-Vinylnaphthalene Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
63444-51-9	6-Methoxy-2-Vinylnaphthalene	ca. 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 63444-51-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H12O
Molecular Weight: 184.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Acids, acid chlorides, acetic anhydride, carbon dioxide, oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 63444-51-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Methoxy-2-Vinylnaphthalene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 63444-51-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 63444-51-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 63444-51-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：用于制备医药中间体。

反应信息

• 作为反应物：
  描述：

  6-甲氧基-2-萘乙烯 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 dicarbonylacetylacetonato rhodium (I) 、 (R,R,R)-bisdiazaphospholane 、 氢气 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 20.0~80.0 ℃ 、2.76 MPa 条件下， 反应 20.8h， 生成 萘普生
  参考文献：
  名称：

  连续的液体蒸汽反应第2部分：立式串联反应器中铑-双氮杂磷催化剂的不对称加氢甲酰化

  摘要：

  2-乙烯基-6-甲氧基萘的不对称加氢甲酰化（AHF）展示了立式串联串联活塞流反应器（PFR）的重要设计特征。AHF反应的区域和对映选择性为流式反应器中的气液混合提供了化学探针，可与搅拌良好的间歇式反应器进行比较。用流动反应器获得的结果优于分批获得的结果。因此，AHF提供了（S）-萘普生的有效的，流中对映选择性合成。

  DOI：

  10.1021/acs.oprd.5b00406
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 四(三苯基膦)钯 碘 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 73.0h， 生成 6-甲氧基-2-萘乙烯
  参考文献：
  名称：

  海藻糖衍生的配体aa和β-tredip的铑配合物催化加氢甲酰化; α-甲基芳基丙醛的高度选择性反应途径

  摘要：

  配体αα-TREDIP的铑配合物在环境条件下在苯乙烯加氢甲酰化中产生62：1的异区域选择性，而没有过量的膦，高于任何先前报道的值。将结果与用其他配体获得的结果进行比较，并扩展到抗炎药萘普生的前体2-（6-甲氧基-2-萘基）-丙醛的制备。

  DOI：

  10.1016/s0040-4020(01)88063-7

文献信息

• Electronic Effects in Asymmetric Catalysis:  Structural Studies of Precatalysts and Intermediates in Rh-Catalyzed Hydrogenation of Dimethyl Itaconate and Acetamidocinnamic Acid Derivatives Using <i>C</i>₂-Symmetric Diarylphosphinite Ligands
  作者：T. V. RajanBabu、Branko Radetich、Kamfia K. You、Timothy A. Ayers、Albert L. Casalnuovo、Joseph C. Calabrese

  DOI：10.1021/jo9901182

  日期：1999.5.1

  largely unaffected by electronic effects, which suggests that other explanations have to be sought for the electronic amplification of enantioselectivity. One possibility is a change in the diastereomeric equilibrium between the initially formed [substrate]Rh(+)[phosphinite] complexes as a function of electronic effect of the ligand. In the Rh-catalyzed hydrogenation of dimethyl itaconate, we have examined

  的Rh（I）的对映选择性的催化的脱氢氨基酸衍生物的不对称氢化和衣康酸二甲酯可以通过对来自碳水化合物以及反式 - 环己烷-1,2-二醇衍生的邻位diarylphosphinites的芳香环的取代基的合适的选择来增强。例如，使用在磷处具有给电子双（3,5-二甲基苯基）基团的次膦酸盐在这些反应中提供了高ee，而吸电子芳基取代基降低了对映选择性。在本文中，我们试图从两个层面上阐明这些非凡的电子效应的起源。首先，确定了多种预催化剂（[亚膦酸酯]（2）Rh（+）[二烯烃] X（-））的晶体结构，并对其结构进行了详细研究，以检查电子效应（如果有），这些分子的基态构象。对其中六种配合物的研究表明，这些预催化剂的总体构象特征在很大程度上不受电子效应的影响，这表明对电子选择性的对映选择性必须寻求其他解释。一种可能是初始形成的[底物] Rh（+）[亚膦酸酯]配合物之间的非对映异构体平衡随配体电子效应的变化而变化
• Pd-Catalyzed Vinylation of Aryl Halides with Inexpensive Organosilicon Reagents Under Mild Conditions
  作者：Chu-Ting Yang、Jun Han、Jun Liu、Yi Li、Fan Zhang、Hai-Zhu Yu、Sheng Hu、Xiaolin Wang

  DOI：10.1002/chem.201802573

  日期：2018.7.20

  Pd‐catalyzed Hiyama vinylation reaction of non‐activated aryl chlorides and bromides under mild conditions was developed. The use of efficient vinyl donors and electron‐rich sterically hindered phosphine ligands was critical for the success of the reaction. The products of this transformation can be used for Am/Cm separation, an important challenge in nuclear fuel reprocessing. The substituent effect

  在温和条件下开发了钯催化未活化的芳基氯和溴化物的Hiyama乙烯基化反应。有效的乙烯基供体和富含电子的位阻膦配体的使用对于反应成功至关重要。这种转化的产物可用于Am / Cm分离，这是核燃料后处理中的一项重要挑战。还获得了取代基对Am / Cm分离选择性的影响，这可能有助于开发用于分离Am和Cm的新型色谱材料。
• Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
  作者：Helen Barlow、Jonas Y. Buser、Hendrik Glauninger、Carla V. Luciani、Joseph R. Martinelli、Niall Oram、Nichole Thompson‐Van Hook、Jeffery Richardson

  DOI：10.1002/adsc.201800167

  日期：2018.7.16

  moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model‐aided reaction optimization was utilized

  丁苯酯是重要且有用的结构部分，但是其制备方法通常具有许多低效的地方。这里介绍的是一种通过连续的Heck反应分两步，一锅制备不对称丁苯甲醚的方法。对于电子分化的萘基溴化物，分析了乙烯气体的第一个Heck反应与温度和压力的关系，并利用模型辅助的反应优化来定义系统。此外，reactNMR用于确定乙烯在可用于Heck反应的普通有机溶剂中的溶解度。最终，开发了优化的顺序Heck反应工艺并将其应用于多种底物，从而可以有效制备不对称的对苯二甲酸酯，包括天然抗氧化剂，紫檀二烯。
• Application of Pd Nanoparticles Supported on Mesoporous Hollow Silica Nanospheres for the Efficient and Selective Semihydrogenation of Alkynes
  作者：Oscar Verho、Haoquan Zheng、Karl P. J. Gustafson、Anuja Nagendiran、Xiaodong Zou、Jan-E. Bäckvall

  DOI：10.1002/cctc.201501112

  日期：2016.2

  Herein, the preparation of a heterogeneous catalyst consisting of 1–2 nm sized Pd nanoparticles supported on amino‐functionalized mesoporous hollow silica nanospheres and its use for the semihydrogenation of mono‐ and disubstituted alkynes is reported. By utilizing this Pd nanocatalyst together with the green poisoning agent DMSO, high yields of the desired alkenes could be achieved, while suppressing

  在本文中，报道了由负载在氨基官能化介孔空心二氧化硅纳米球上的1-2 nm大小的Pd纳米颗粒组成的非均相催化剂的制备及其在单和双取代炔烃的半氢化反应中的应用。通过将此Pd纳米催化剂与绿色中毒剂DMSO一起使用，可以实现所需烯烃的高收率，同时抑制了烷烃过度还原的程度。令我们高兴的是，Pd纳米催化剂对炔烃部分表现出卓越的化学选择性，从而可以在其他可还原的官能团（例如卤素，羰基和硝基）存在下进行转化。
• Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent
  作者：Xiao-Ping Wang、Jin-Hong Lin、Cheng-Pan Zhang、Ji-Chang Xiao、Xing Zheng

  DOI：10.3762/bjoc.9.299

  日期：——

  An efficient method for the copper-catalyzed trifluoromethylation of terminal alkenes with an electrophilic trifluoromethylating reagent has been developed. The reactions proceeded smoothly to give trifluoromethylated alkenes in good to excellent yields. The results provided a versatile approach for the construction of Cvinyl-CF3 bonds without using prefunctionalized substrates.

  已经开发了一种使用亲电三氟甲基化试剂对末端烯烃进行铜催化三氟甲基化的有效方法。反应顺利进行，以良好到极好的产率得到三氟甲基化烯烃。结果提供了一种无需使用预官能化底物即可构建 Cvinyl-CF3 键的通用方法。