5-(4-氟苯基)-2-甲基-3-呋喃羧酸乙酯 | 111787-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-(4-氟苯基)-2-甲基-3-呋喃羧酸乙酯
• 中文别名: 乙基5-(4-氟苯基)-2-甲基-3-糠酸酯
• 英文名称: ethyl 5-(4-fluorophenyl)-2-methylfuran-3-carboxylate
• 英文别名: Ethyl 5-(4-fluorophenyl)-2-methyl-3-furoate
• CAS: 111787-83-8
• 化学式: C₁₄H₁₃FO₃
• 分子量: 248.254
• InChiKey: XUYCJNMLONEKAS-UHFFFAOYSA-N

物化性质

• 沸点：
  154 °C
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  4

SDS

Name:	Ethyl 5-(4-fluorophenyl)-2-methyl-3-furoate Material Safety Data Sheet
Synonym:	None Known
CAS:	111787-83-8

Section 1 - Chemical Product MSDS Name:Ethyl 5-(4-fluorophenyl)-2-methyl-3-furoate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
111787-83-8	Ethyl 5-(4-fluorophenyl)-2-methyl-3-fu	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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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.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 111787-83-8: 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: Low melting solid
Color: Green
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 154 - 158 deg C @3mm Hg
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: C14H13FO3
Molecular Weight: 248.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong bases, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 111787-83-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 5-(4-fluorophenyl)-2-methyl-3-furoate - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
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.
WGK (Water Danger/Protection)
CAS# 111787-83-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 111787-83-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 111787-83-8 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：

  5-(4-氟苯基)-2-甲基-3-呋喃羧酸乙酯 在 lithium aluminium tetrahydride 、 三溴化磷 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 50.0h， 生成 1-[[5-(4-fluorophenyl)-2-methylfuran-3-yl]methyl]-4-methylimidazole
  参考文献：
  名称：

  Porretta; Scalzo; Chimenti, Farmaco, Edizione Scientifica, 1987, vol. 42, # 5, p. 629 - 639

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基-4-(4-氟苯基)-4-氧代丁酸乙酯 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到5-(4-氟苯基)-2-甲基-3-呋喃羧酸乙酯
  参考文献：
  名称：

  Porretta; Scalzo; Chimenti, Farmaco, Edizione Scientifica, 1987, vol. 42, # 5, p. 629 - 639

  摘要：

  DOI：

文献信息

• Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: a direct synthesis of trisubstituted furans
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2014.07.086

  日期：2014.9

  method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to wide substrate scope. Moreover, this synthesis employs cheap Cu(MeCN)4PF6 as the catalyst and no additional ligand is needed. Similar reaction has also been

  基于Cu（I）催化的末端炔烃与β-酮α-重氮酸酯的反应，已经开发了一种三取代呋喃的合成方法。该合成2,3,5-三取代呋喃的方法操作简单，适用于广泛的底物范围。此外，该合成采用廉价的Cu（MeCN）4 PF 6作为催化剂，不需要其他配体。类似的反应也已用于（E）-2-重氮-3-（甲氧基亚氨基）丁酸乙酯，用于合成2,3,5-三取代的N-甲氧基吡咯，但效果有限。
• Copper-Mediated [3 + 2] Oxidative Cyclization Reaction of <i>N</i>-Tosylhydrazones and β-Ketoesters: Synthesis of 2,3,5-Trisubstituted Furans
  作者：Yubing Huang、Xianwei Li、Yue Yu、Chuanle Zhu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b00568

  日期：2016.6.17

  The first attempt utilizing N-tosylhydrazones as two-carbon synthons has been successfully achieved, which underwent a copper-mediated [3 + 2] oxidative cyclization reaction to afford 2,3,5-trisubstituted furans in moderate to good yields. The features of this method include inexpensive metal catalyst, readily available substrates, high regioselectivity and convenient operation. The studies provide

  已成功实现了使用N-甲苯磺酰hydr作为二碳合成子的首次尝试，该尝试进行了铜介导的[3 + 2]氧化环化反应，以中等至良好的收率提供了2,3,5-三取代的呋喃。该方法的特征包括廉价的金属催化剂，易于获得的底物，高区域选择性和方便的操作。这些研究为进一步探索N-甲苯磺酰hydr的强大而多样的反应能力提供了重要的途径。
• Synthesis of polysubstituted furans from aryl gem-dibromoethenes
  作者：Wensheng Zhang、Wenjing Xu

  DOI：10.1007/s10593-017-2100-2

  日期：2017.5

  Synthesis of 2,3,5-trisubstituted furans can be performed at 120°C in DMF using aryl gem-dibromoethenes and ethyl acetoacetate as the starting substrates under the assistance of Ag2CO3–Cs2CO3–KOAc system. The structures of the products were confirmed by IR, 1H, 13C NMR spectroscopy and elemental analysis.

  2,3,5-三取代呋喃的合成可以在DMF中于120°C下进行，使用Ag 2 CO 3 -Cs 2 CO 3 -KOAc体系辅助的芳基宝石-二溴乙烯和乙酰乙酸乙酯作为起始底物。产物的结构通过IR，1 H，13 C NMR光谱和元素分析确认。
• Tuning radical reactivity using iodine in oxidative C(sp³)–H/C(sp)–H cross-coupling: an easy way toward the synthesis of furans and indolizines
  作者：Shan Tang、Kun Liu、Yue Long、Xiaotian Qi、Yu Lan、Aiwen Lei

  DOI：10.1039/c5cc01825k

  日期：——

  Molecular iodine was found to be an effective redox catalyst for the oxidative cross-coupling of carbonyl compounds with terminal alkynes.

  分子碘被发现是一种有效的氧化还原催化剂，可用于羰基化合物与末端炔烃的氧化交叉偶联反应。
• Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, and Thiophenes
  作者：Wei Wen Tan、Naohiko Yoshikai

  DOI：10.1021/acs.joc.6b00904

  日期：2016.7.1

  We report herein copper(II)-catalyzed cyclization reactions of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones to afford 2-siloxy-2,3-dihydrofuran derivatives or 2,3,5-trisubstituted furans, respectively, under mild conditions. The former cyclization products serve as versatile 1,4-diketone surrogates, allowing facile preparation of 2,3,5-trisubstituted furans

  我们在本文中报道了铜（II）催化的甲基酮衍生的甲硅烷基烯醇醚与α-重氮-β-酮酸酯或α-二氮酮的环化反应，从而提供2-siloxy-2,3-dihydrofuran衍生物或2,3,5-三取代的呋喃，分别在温和的条件下。以前的环化产品可以用作通用的1,4-二酮替代物，从而可以轻松制备2,3,5-三取代的呋喃，吡咯和噻吩。