甲基2-氟苯乙酸 | 57486-67-6

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯乙酸系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基2-氟苯乙酸
• 中文别名: 2-氟苯乙酸甲酯；甲基-2-氟乙酸苯酯
• 英文名称: methyl o-fluorophenylacetate
• 英文别名: methyl 2-(2-fluorophenyl)acetate；methyl 2-fluorophenylacetate
• CAS: 57486-67-6
• 化学式: C₉H₉FO₂
• mdl: MFCD00800605
• 分子量: 168.168
• InChiKey: TWXVEZBPKFIMBB-UHFFFAOYSA-N

物化性质

• 沸点：
  210°C (rough estimate)
• 密度：
  1.1410 (estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2916399090
• 储存条件：
  存于阴凉干燥处

SDS

Name:	Methyl 2-Fluorophenylacetate Material Safety Data Sheet
Synonym:	None
CAS:	57486-67-6

Section 1 - Chemical Product MSDS Name:Methyl 2-Fluorophenylacetate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57486-67-6	Methyl 2-fluorophenylacetate	99	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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:

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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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 57486-67-6: 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: Liquid
Color: clear, colorless
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: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H9FO2
Molecular Weight: 168.06

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, fluoride fumes.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 57486-67-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 2-fluorophenylacetate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 57486-67-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 57486-67-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 57486-67-6 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：

  甲基2-氟苯乙酸 在 吡啶 、 hydrazine hydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 二甲基亚砜 、 sodium chloride 、 lithium hexamethyldisilazane 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine
  参考文献：
  名称：

  Discovery of the Soluble Guanylate Cyclase Stimulator Vericiguat (BAY 1021189) for the Treatment of Chronic Heart Failure

  摘要：

  The first-in-class soluble guanylate cyclase (sGC) stimulator riociguat was recently introduced as a novel treatment option for pulmonary hypertension. Despite its outstanding pharmacological profile, application of riociguat in other cardiovascular indications is limited by its short half-life, necessitating a three times daily dosing regimen. In our efforts to further optimize the compound class, we have uncovered interesting structure activity relationships and were able to decrease oxidative metabolism significantly. These studies resulting in the discovery of once daily sGC stimulator vericiguat (compound 24, BAY 1021189), currently in phase 3 trials for chronic heart failure, are now reported.

  DOI：

  10.1021/acs.jmedchem.7b00449
• 作为产物：
  描述：

  2-氟苯乙酸 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 甲基2-氟苯乙酸
  参考文献：
  名称：

  3-aroylbenzylpyridazinone derivatives

  摘要：

  公式I的化合物：##STR1## 其中：R.sub.10是由公式(A)、(B)或(C)表示的基团：##STR2## 其他取代基如规范中所定义；它们的药用盐是前列腺素G/H合酶的抑制剂，具有抗炎和镇痛作用。

  公开号：

  US05886178A1

文献信息

• Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors
  作者：Bichao Song、Peipei Xie、Yingzi Li、Jiping Hao、Lu Wang、Xiangyang Chen、Zhongliang Xu、Haitian Quan、Liguang Lou、Yuanzhi Xia、K. N. Houk、Weibo Yang

  DOI：10.1021/jacs.0c00078

  日期：2020.6.3

  The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadiene, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) car-bene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones

  多取代丁二烯尤其是多功能丁二烯的高效立体选择性合成是有机合成中的一大挑战。在此，我们希望报告一种独特的 Pd(0) 碳烯引发的脱羧烯化方法，该方法能够将重氮酯与乙烯基碳酸亚乙酯 (VEC)、乙烯基恶唑烷酮或乙烯基苯并恶嗪酮直接偶联，以提供醇、胺或苯胺。含有 1,3-二烯，产率中等至高，具有出色的立体选择性。该协议具有操作简单、反应条件温和、底物范围广泛和可扩展性等特点。值得注意的是，分离并表征了一种结构独特的烯丙基 Pd(II) 中间体。DFT 计算和控制实验表明，稀有的 Pd(0) 卡宾中间体可能参与该反应。此外，作为新型构件的多取代丁二烯前所未有地组装成大环化合物，有效抑制了 P-糖蛋白 (P-gp)，并以 190 倍的速度显着逆转了癌细胞的多药耐药性。
• Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C–H Activation
  作者：Xiai Luo、Yankun Xu、Genhua Xiao、Wenjuan Liu、Cheng Qian、Guobo Deng、Jianxin Song、Yun Liang、Chunming Yang

  DOI：10.1021/acs.orglett.8b00982

  日期：2018.5.18

  with two aryl iodides for the synthesis of spirooxindole has been achieved. The reaction underwent the process of triple C–H activation and four C–C bond formations based on the double trapping of transient spirocyclic palladacycles which are obtained through remote C–H activation.

  已经实现了新颖的钯催化的N-（2-碘芳基）丙烯酰胺与两个芳基碘化物的串联反应，用于合成螺并吲哚。该反应经历了三重C–H活化和四个C–C键形成的过程，该过程基于通过远程C–H活化获得的瞬时螺环式Palladacycles的双重捕获。
• Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis
  作者：Kaining Zhang、Liang Chang、Qing An、Xin Wang、Zhiwei Zuo

  DOI：10.1021/jacs.9b05932

  日期：2019.7.3

  functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional

  脱羟甲基化是将醇原料直接转化为少一个碳原子的烷基合成子，是一种利用醇材料的普遍性和稳健性的非常规且未充分探索的策略。在温和且氧化还原中性的反应条件下，利用廉价的铈催化剂，提供了光催化脱羟甲基化平台。通过配体到金属的电荷转移催化，醇官能团已可靠地转移到亲核自由基中，同时失去一分子甲醛。有趣的是，我们发现铈催化剂可以显着促进脱羟甲基化过程，并且碎片自由基的稳定作用也起着重要作用。这种操作简单的方案能够直接利用伯醇作为非常规烷基亲核试剂，用于自由基介导的 1,4-共轭加成与迈克尔受体。广泛的醇类，从简单的乙醇到复杂的核苷和类固醇，已成功应用于这种片段偶联转化。此外，该催化系统的模块化已在多种自由基介导的转化中得到证实，包括氢化、胺化、烯基化和氧化。
• [EN] ALKALOID AMINOESTER DERIVATIVES AND MEDICINAL COMPOSITION THEREOF<br/>[FR] DÉRIVÉS AMINOESTÉRIFIÉS D'ALCALOÏDES ET COMPOSITION MÉDICINALE LES INCLUANT
  申请人：CHIESI FARMA SPA

  公开号：WO2010072338A1

  公开（公告）日：2010-07-01

  The present invention relates to alkaloid aminoester derivatives acting as muscarinic receptor antagonists, to methods of preparing such derivatives, to compositions comprising them and therapeutic use thereof.

  本发明涉及作为毒蕈碱受体拮抗剂的生物碱氨基酸酯衍生物，制备此类衍生物的方法，包含它们的组合物以及它们的治疗用途。
• Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates
  作者：Longzhu Bao、Shuangshuang Wang、Di Song、Jingjing Wang、Xiufang Cao、Shaoyong Ke

  DOI：10.3390/molecules24071304

  日期：——

  A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

  一系列新颖的3-芳基-4-羟基-2(5H) 呋喃酮-丙烯酸酯混合物是基于天然丁内酯和丙烯酸酯骨架设计和合成的。所制备化合物的结构经过1H-NMR、13C-NMR和电喷雾电离质谱（ESI-MS）表征，对目标化合物对十二种植物病原真菌的生物活性进行了研究。初步的体外抗真菌活性筛选显示，大多数目标化合物在浓度为100 mg·L−1时对各种病原真菌有中等抑制作用，并表现出广谱抗真菌活性。进一步研究还表明，化合物7e和7k在较低浓度下仍对油菜植物上的茶树萎凋病、软腐病和赤霉病菌有一定的抑制活性，可作为进一步研究的次级引物进行优化。