5-(4-氟苯基)异恶唑 | 138716-37-7

• 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: 5-(4-氟苯基)异恶唑
• 中文别名: 5-(4-氟苯基)异噁唑
• 英文名称: 5-(4-fluorophenyl)isoxazole
• 英文别名: 5-(4-fluorophenyl)-1,2-oxazole
• CAS: 138716-37-7
• 化学式: C₉H₆FNO
• 分子量: 163.151
• InChiKey: JZCBQTRPILCIBC-UHFFFAOYSA-N

物化性质

• 熔点：
  53-56°C
• 沸点：
  275.8±15.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规定使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 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：
  26
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-(4-Fluorophenyl)isoxazole
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-(4-Fluorophenyl)isoxazole
CAS number: 138716-37-7

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H6FNO
Molecular weight: 163.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen fluoride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(4-氟苯基)异恶唑 在 potassium hydroxide 、 肼 作用下， 以 乙醇 、 水 、 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.0h， 以92%的产率得到3-(4-氟苯基)-1H-吡唑-5-胺
  参考文献：
  名称：

  由异恶唑合成氨基吡唑：原位NMR分析制备方法的比较

  摘要：

  摘要 提出并比较了由异恶唑合成氨基吡唑的一步法和两步法。基于原位NMR监测，这两个过程均通过酮腈进行。在一步法中，肼用于将异恶唑与未分离的酮腈中间体开放，并形成氨基吡唑。该两步法涉及通过用氢氧化物使质子脱氢以生成乙腈，然后加入乙酸和肼以形成氨基吡唑，从而使异恶唑开环。 提出并比较了由异恶唑合成氨基吡唑的一步法和两步法。基于原位NMR监测，这两个过程均通过酮腈进行。在一步法中，肼用于将异恶唑与未分离的酮腈中间体开放，并形成氨基吡唑。该两步法涉及通过用氢氧化物使质子脱氢以生成乙腈，然后加入乙酸和肼以形成氨基吡唑，从而使异恶唑开环。

  DOI：

  10.1055/s-0035-1561861
• 作为产物：
  描述：

  3-(4-fluorophenyl)-3-oxopropanal 在 盐酸羟胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 生成 5-(4-氟苯基)异恶唑
  参考文献：
  名称：

  Identification and optimisation of 5-amino-7-aryldihydro-1,4-diazepines as 5-HT2A ligands

  摘要：

  A several series of low molecular weight 5-HT2A leads were identified from an analysis of HTS data, the exploration of SAR and optimization of one series using parallel synthesis are described, affording compound 22 (5-HT2A IC50 1.1 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.108

文献信息

• Harnessing Stereospecific <i>Z</i>-Enamides through Silver-Free Cp*Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles
  作者：Suvankar Debbarma、Sourav Sekhar Bera、Modhu Sudan Maji

  DOI：10.1021/acs.orglett.8b04130

  日期：2019.2.1

  The stereospecific synthesis of Z-enamides is described in this paper. For the first time, isoxazoles have been employed as electrophiles in C–H functionalization to afford thermodynamically less stable Z-enamides utilizing salicylaldehydes in an atom- and step-economic fashion. The stereochemistry of enamides might originate from the relative disposition of atoms present in isoxazole and the intramolecular

  本文描述了Z-烯酰胺的立体有择合成。首次将异恶唑用作C–H功能化过程中的亲电子试剂，从而以原子经济和分步经济的方式利用水杨醛提供热力学上较不稳定的Z-酰胺。烯酰胺的立体化学可能源自异恶唑中存在的原子的相对位置和分子内氢键。由于多种结构上和电子上不同的水杨醛和异恶唑能有效反应，因此该反应显示出极好的范围。
• Reaction of β-dimethylaminovinyl ketones with hydroxylamine: A simple and useful method for synthesis of 3- and 5-substituted isoxazoles
  作者：Fernanda A. Rosa、Pablo Machado、Helio G. Bonacorso、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1002/jhet.5570450337

  日期：2008.5

  The regioselective synthesis of 3- and 5-substituted-isoxazoles from the reaction of β-dimethyl-aminovinyl ketones [R-C(O)CHCH-NMe2, where R Ph, MeO-4-C6H4, F-4-C6H4, Cl-4-C6H4, Br-4-C6H4, O2N-4-C6H4, fur-2-yl, thien-2-yl, pyrrol-2-yl, Et and CCl3] and hydroxylamine hydrochloride varying only the reaction conditions (with and without the addition of pyridine) is reported.

  由β-二甲基氨基乙烯基酮[RC（O）CH CH-NMe 2，其中R Ph，MeO-4-C 6 H 4，F-4- C 6 H 4，Cl-4-C 6 H 4，Br-4-C 6 H 4，O 2 N-4-C 6 H 4，呋喃-2-基，噻吩-2-基，吡咯-2-报道了仅改变反应条件（添加和不添加吡啶）的烷基，Et和CCl 3 ]和盐酸羟胺。
• TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN₃
  作者：Yan He、Yu-yang Xie、Ying-chun Wang、Xiao-min Bin、Da-chao Hu、Heng-shan Wang、Ying-ming Pan

  DOI：10.1039/c6ra11099a

  日期：——

  A novel and efficient TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN3 via a radical mechanism process is described. This methodology provides an easy access to a variety of useful 5-substituted isoxazoles from simple and readily available propargylic ketones and TMSN3 in good to excellent yields. A plausible reaction mechanism for this process is proposed.

  描述了一种新颖有效的TEMPO催化通过自由基机理过程从炔丙基酮和TMSN 3 合成5-取代异恶唑的方法。这种方法可以轻松简便地从简单易得的炔丙基酮和TMSN 3中获得各种有用的5-取代的异恶唑，收率良好。提出了该过程的合理反应机理。
• A novel synthesis of 5-substituted isoxazoles from propargylic amines and N -hydroxyphthalimide
  作者：Yicheng Zhang、Wei Chen、Xueshun Jia

  DOI：10.1016/j.tetlet.2018.04.062

  日期：2018.5

  A mild and efficient method for the synthesis of 5-substituted isoxazoles through cyclization of propargylic amines with N-hydroxyphthalimide (NHPI) under metal-free conditions was developed.

  开发了一种温和有效的方法，该方法通过在无金属条件下用N-羟基邻苯二甲酰亚胺（NHPI）环化炔丙基胺来合成5-取代的异恶唑。
• 一种叠氮和炔酮化合物合成异噁唑类化合物 的制备方法
  申请人：广西师范大学

  公开号：CN105924405B

  公开（公告）日：2018-05-01

  本发明公开了一种叠氮和炔酮化合物合成异噁唑类化合物的方法，包括步骤为：1）加入30 mol%的催化剂，10当量的水及5~10倍量的极性溶剂，通入空气或是敞口，在室温下搅拌24 h；2）再加入20当量的三苯基膦，在室温下继续搅拌反应2 h，TLC跟踪反应；3）待反应完全后，将反应物倒入10~30mL水中；4）然后用20~30mL二氯甲烷萃取，通过饱和食盐水（10~20 mL）洗涤三次，之后用无水Na2SO4干燥，过滤，减压除去溶剂，经快速硅胶柱层析纯化得产物。本方法实验所需操作简单，原料易得，反应步骤少，产量高，具有很好的应用价值，适合于医药、农药方面的应用，有良好的应用前景。