2-(2-萘基)乙酰氯 | 37859-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(2-萘基)乙酰氯
• 英文名称: 2-naphthylacetyl chloride
• 英文别名: 2-(naphthalen-2-yl)acetyl chloride；2-(2-naphthyl)ethanoyl chloride；2-(2-naphthyl)acetyl chloride；2-naphthalen-2-ylacetyl chloride
• CAS: 37859-25-9
• 化学式: C₁₂H₉ClO
• 分子量: 204.656
• InChiKey: QEJGMKHQXSZCOS-UHFFFAOYSA-N

物化性质

• 熔点：
  61-65°C
• 沸点：
  156-158 °C(Press: 10 Torr)
• 密度：
  5 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 危险品运输编号：
  UN 3261
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P260,P264,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P321,P363,P405,P501
• 危险性描述：
  H314
• 储存条件：
  存储条件：2-8°C，建议使用惰性气体保护。

SDS

Name:	2-(2-Naphthyl)acetyl chloride tech Material Safety Data Sheet
Synonym:
CAS:	37859-25-9

Section 1 - Chemical Product MSDS Name:2-(2-Naphthyl)acetyl chloride tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
37859-25-9	2-(2-Naphthyl)acetyl chloride		unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Air sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under an inert atmosphere.

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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# 37859-25-9: Personal Protective Equipment Eyes: Not available.
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: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 61 - 65 deg C
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: C12H9ClO
Molecular Weight: 205

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to air, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases, alcohols.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 37859-25-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(2-Naphthyl)acetyl chloride - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 37859-25-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 37859-25-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 37859-25-9 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

反应信息

• 作为反应物：
  描述：

  2-(2-萘基)乙酰氯 在 三乙烯二胺 、 正丁基锂 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S)-2,3-dinaphthalen-2-yl-1,4-bis[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butane-1,4-dione
  参考文献：
  名称：

  通过手性3-（芳基乙酰基）-2-恶唑烷酮的氧化均偶联反应不对称合成旋光的2,3-二芳基琥珀酸

  摘要：

  通过用DABCO-TiCl 4或DMAP-TiCl 4处理，实现手性3-（芳基乙酰基）-2-恶唑烷酮1的氧化均偶联，并立体定向提供相应的二聚体。（4S）-和（4R）-取代的1的反应得到（S，S）-和（R，R）-二聚体。获得的二聚体容易转化为相应的2，3-二芳基琥珀酸。因此，该反应提供了用于合成光学纯的2，3-二芳基琥珀酸的有用方法。芳基上的给电子基团的对位取代不会抑制氧化偶合。然而，对位取代的吸电子基团和邻位取代基阻碍了偶联。

  DOI：

  10.1016/s0040-4020(98)83006-8
• 作为产物：
  描述：

  tert-butyl (naphthalen-2-yl)acetate 在 三氯化磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2-(2-萘基)乙酰氯
  参考文献：
  名称：

  PCl 3介导的酰氯形成对叔丁基酯进行酯交换和氨解

  摘要：

  在空气中一锅中开发了PCl 3介导的叔丁基酯向酯和酰胺的转化。生物活性分子骨架的合成和克级反应突显了这种新颖的方案。机理研究表明，这种转化涉及原位形成酰氯，然后与醇或胺反应以提供所需的产物。

  DOI：

  10.1177/1747519820987530

文献信息

• Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group
  作者：Jignesh J. Patel、Marju Laars、Wei Gan、Johnathan Board、Matthew O. Kitching、Victor Snieckus

  DOI：10.1002/anie.201805203

  日期：2018.7.20

  general synthesis of highly substituted 2‐naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z‐cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation

  演示了基于新的碳负离子反应序列的高度取代的2-萘酚的一般合成。该反应利用了锂碱的双重性质，即将容易获得的具有LiNEt 2或LiN i Pr 2的香豆素连续开环成Z肉桂酰胺，从而在原位生成一个导向基团，并通过构象自由度允许横向定向的远程金属化以进行闭环反应，得到芳基2-萘酚，收率好至极好。可以将这些转换组合起来，以提供更有效的单锅法。对远端横向金属化步骤的机械洞察力，证明了对Z的要求描述了肉桂酰胺。还报道了该方法在高度取代的3,3'-二芳基BINOL配体合成中的应用。
• Biochemical, Structural, and Biological Evaluation of Tranylcypromine Derivatives as Inhibitors of Histone Demethylases LSD1 and LSD2
  作者：Claudia Binda、Sergio Valente、Mauro Romanenghi、Simona Pilotto、Roberto Cirilli、Aristotele Karytinos、Giuseppe Ciossani、Oronza A. Botrugno、Federico Forneris、Maria Tardugno、Dale E. Edmondson、Saverio Minucci、Andrea Mattevi、Antonello Mai

  DOI：10.1021/ja101557k

  日期：2010.5.19

  demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically

  LSD1 和 LSD2 组蛋白去甲基化酶涉及许多生理和病理过程，从肿瘤发生到疱疹病毒感染。这里介绍了一项全面的结构、生化和细胞研究，以探索这些酶在表观遗传疗法中的潜力。这种方法使用反苯环丙胺作为设计新型去甲基酶抑制剂的化学支架。这种药物是一种经过临床验证的抗抑郁药，已知靶向单胺氧化酶 A 和 B。这两种黄素酶在结构上与 LSD1 和 LSD2 相关。反苯环丙胺抑制的机理和晶体学研究表明，根据对映体形式，FAD 辅因子缺乏选择性和不同的共价修饰。这些发现在药理学上是相关的，因为反苯环丙胺目前作为外消旋混合物给药。合成了大量反苯环丙胺类似物并筛选了抑制活性。我们发现 LSD 和 MAO 酶的共同进化起源，尽管它们的功能和底物特异性无关，但反映在相关的配体结合特性上。鉴定了一些具有部分酶选择性的化合物。这些新抑制剂之一的生物活性是用选择的急性早幼粒细胞白血病细胞模型评估的，因为其发病机制包括几种
• Novel Deoxyxylulosephosphate-Reductoisomerase Inhibitors: Fosmidomycin Derivatives with Spacious Acyl Residues
  作者：Regina Ortmann、Jochen Wiesner、Katrin Silber、Gerhard Klebe、Hassan Jomaa、Martin Schlitzer

  DOI：10.1002/ardp.200700149

  日期：2007.9

  enzyme of the mevalonate‐independent pathway of the isoprenoid biosynthesis. Using fosmidomycin as a specific inhibitor of Dxr, this enzyme was previously validated as target for the treatment of malaria and bacterial infections. The replacement of the formyl residue of fosmidomycin by spacious acyl residues yielded inhibitors active in the micromolar range. As predicted by flexible docking, evidence was

  1 - 脱氧 - D - 木酮糖 - 5 - 磷酸还原异构酶 (Dxr) 代表类异戊二烯生物合成的非甲羟戊酸途径的必需酶。使用 fosmidomycin 作为 Dxr 的特异性抑制剂，这种酶以前被验证为治疗疟疾和细菌感染的靶点。fosmidomycin 的甲酰基残基被宽敞的酰基残基取代产生了在微摩尔范围内有活性的抑制剂。正如柔性对接所预测的那样，获得了在酰基残基中适当放置的羰基与位于酶的柔性催化环中的 Met214 的主链 NH 之间形成氢键的证据。
• Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS₂ to form 2-thineyl vinyl sulfide
  作者：Weihong Fei、Ping Xu、Jie Hou、Weijun Yao

  DOI：10.1039/d0cc05070a

  日期：——

  have developed a DPPE-catalyzed three molecular two component tandem reaction of γ-substituted allenoate and CS2 to construct 2-thineyl vinyl sulfide through phosphine catalyzed [3+2] cyclization followed by Michael addition. The synthetic value of the 2-thineyl vinyl sulfide was demonstrated by a concise synthesis of an anti-glaucoma agent.

  我们已经开发了DPPE催化的γ-取代的脲基甲酸酯和CS 2的三分子两组分串联反应，通过膦催化的[3 + 2]环化反应和随后的Michael加成反应来构建2-硫代乙烯基乙硫醚。通过精确合成抗青光眼剂证明了2-亚硫基乙烯基硫的合成值。
• Trapping Intermediates in an [8 + 2] Cycloaddition Reaction with the Help of DFT Calculations
  作者：Marta L. Lage、Israel Fernández、Miguel A. Sierra、M. Rosario Torres

  DOI：10.1021/ol200910z

  日期：2011.6.3

  DFT calculations predict that the [8 + 2] cycloaddition reaction between ketenes and 8-azaheptafulvenes occurs stepwise through antiaromatic zwitterionic intermediates. With adequate modifications of both the electronic properties of the ketene and the reaction conditions, these elusive intermediates have been successfully trapped and fully characterized (X-ray), thus confirming the predicted stepwise

  DFT计算预测，烯酮与8-azaheptafulvenes之间的[8 + 2]环加成反应是通过抗芳香族两性离子中间体逐步发生的。通过对乙烯酮的电子性质和反应条件进行适当的修改，这些难以捉摸的中间体已被成功捕获并完全表征（X射线），从而证实了预测的逐步转化性质。