3-(2,6-二氯苯基)-5-甲基异噁唑-4-羧酸甲酯 | 4402-83-9

• 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: 3-(2,6-二氯苯基)-5-甲基异噁唑-4-羧酸甲酯
• 英文名称: methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate
• 英文别名: SPB 06193；methyl 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 4402-83-9
• 化学式: C₁₂H₉Cl₂NO₃
• 分子量: 286.114
• InChiKey: YPCASVCAZYPZOI-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  382.4±42.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）、氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090

SDS

Name:	Methyl 3-(2 6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	4402-83-9

Section 1 - Chemical Product MSDS Name:Methyl 3-(2 6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4402-83-9	Methyl 3-(2,6-dichlorophenyl)-5-methyl	97%	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.
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:
Not available.

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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.
Ingestion:
Get medical aid. 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 4402-83-9: 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: white crystalline solid
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 115 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: C12H9Cl2NO3
Molecular Weight: 286

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, oxidizing agents, bases.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4402-83-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 4402-83-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4402-83-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4402-83-9 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：

  3-(2,6-二氯苯基)-5-甲基异噁唑-4-羧酸甲酯 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid anilide
  参考文献：
  名称：

  1120. 6-氨基青霉烯酸的衍生物。第八部分 3-O-氯代苯基-5-甲基-4-异恶唑基烯基林的进一步类似物

  摘要：

  DOI：

  10.1039/jr9650005976
• 作为产物：
  描述：

  (E)-2,6-二氯苯甲醛肟 在 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-(2,6-二氯苯基)-5-甲基异噁唑-4-羧酸甲酯
  参考文献：
  名称：

  新型非甾体类法呢素X受体（FXR）拮抗剂的设计，合成和生物学评估：FXR拮抗作用的分子基础

  摘要：

  法尼醇X受体（FXR）在胆固醇，脂质和葡萄糖代谢的调节中起着重要作用。近来，已经报道了关于FXR拮抗作用的分子基础的一些研究。然而，这些研究均未使用具有非甾体支架的FXR拮抗剂。基于我们先前报道的具有三取代异恶唑支架的FXR拮抗剂，设计了一种新型非甾体FXR配体，并用作结构修饰的先导。总共设计并合成了39种新的三取代异恶唑衍生物，其药理学特征从激动剂到拮抗剂再到FXR。值得注意的是，化合物5s（4'-[（3-3 -[[3-（2-氯苯基）-5-（2-噻吩基）异恶唑-4-基]甲氧基} -1 H-吡唑-1-基）甲基]联苯-2-羧酸），含一个噻吩基取代的异恶唑环，显示针对FXR具有良好的细胞效力（IC最好拮抗活性50 = 12.2±0.2μ中号）。最终，该化合物在分子动力学模拟分析中用作探针。我们的结果使我们能够提出FXR拮抗作用的重要分子基础，这与先前报道的拮抗机制是一致的。此外，发现H12上的

  DOI：

  10.1002/cmdc.201500136

文献信息

• Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp ®
  作者：Christopher J. Easton、Graham A. Heath、C. Merrîcc M. Hughes、Connie K. Y. Lee、G. Paul Savage、Gregory W. Simpson、Edward R. T. Tiekink、George J. Vuckovic、Richard D. Webster

  DOI：10.1039/b008081k

  日期：——

  Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N–O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp®. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

  4位带有吸电子基团的异恶唑在电化学和酵母催化下发生N–O键断裂。电解过程更为高效，并且对于酰基和烷氧羰基取代的异恶唑，它能生成草剂Grasp®所特有的烯醇化双羰基亚胺结构功能。通过使用卤素作为立体辅助控制反应区域化学的氰氧基团环加成反应，可以获得4位和5位取代的异恶唑的区域异构体。化合物11和19b的晶体数据已给出。
• IL17 AND IFN-GAMMA INHIBITION FOR THE TREATMENT OF AUTOIMMUNE INFLAMMATION
  申请人：LEBAN Johann

  公开号：US20120196861A1

  公开（公告）日：2012-08-02

  The present invention relates to compounds of the general formula (I), and the pharmaceutically acceptable salt or solvate thereof, as anti-inflammatory and immunomodulatory agents.

  本发明涉及通式（I）的化合物，以及其药用可接受的盐或溶剂，作为抗炎和免疫调节剂。
• Design, Synthesis, and Bioevaluation of Substituted Phenyl Isoxazole Analogues as Herbicide Safeners
  作者：Ke-Liang Guo、Li-Xia Zhao、Zi-Wei Wang、Ying-Chao Gao、Juan-Juan Li、Shuang Gao、Ying Fu、Fei Ye

  DOI：10.1021/acs.jafc.0c01867

  日期：2020.9.30

  Herbicide safeners enhance herbicide detoxification in crops without affecting target weed sensitivity. To enhance crop tolerance to the toxicity-related stress caused by the herbicide acetochlor (ACT), a new class of substituted phenyl isoxazole derivatives was designed by an intermediate derivatization method as herbicide safeners. Microwave-assisted synthesis was used to prepare the phenyl isoxazole

  除草剂安全剂可增强农作物除草剂的解毒能力，而不会影响目标杂草的敏感性。为了提高农作物对除草剂乙草胺（ACT）引起的毒性相关胁迫的耐受性，通过中间衍生化方法设计了一类新型的取代苯基异恶唑衍生物作为除草剂安全剂。使用微波辅助合成制备苯基异恶唑类似物，并通过IR，1 H NMR，13 C NMR和HRMS确认所有结构。通过X射线衍射分析进一步表征化合物I-1。生物测定结果表明，大多数获得的化合物通过增加玉米生长恢复率，谷胱甘肽含量和谷胱甘肽提供了不同程度的抗ACT诱导伤害的安全性S-转移酶活性。特别地，化合物I-20显示出优异的抗ACT毒性的安全剂活性，可与市售安全剂贝诺沙星相比。进行了高斯计算，结果表明化合物I-20的亲核能力高于贝诺沙星，因此活性高于贝诺沙克。这些发现表明，苯基异恶唑衍生物具有在玉米田中进行保护性管理的巨大潜力。
• Highly Modular Flow Cell for Electroorganic Synthesis
  作者：Christoph Gütz、Andreas Stenglein、Siegfried R. Waldvogel

  DOI：10.1021/acs.oprd.7b00123

  日期：2017.5.19

  application of expensive and nonmachinable electrode materials like boron-doped diamond or glassy carbon can easily be realized in flow cells. By this geometry, the maximum surface of such valuable electrode materials is exploited. The cell size can compete with classical preparative approaches in terms of performance and productivity. The optimization of reaction parameters and an easy up-scaling to larger

  报道了高度模块化的电化学流动池及其在有机合成中的应用。这种创新的设置从多个方面促进了工作：轻松调整电极距离，快速更换电极材料以及轻松在已拆分或未拆分的电池之间切换的可能性。但是，电池的主要优点是将电极材料精确地热定位到特氟龙片中。由此，可以容易地在流通池中实现昂贵且不可加工的电极材料的应用，例如掺硼金刚石或玻璃碳。通过这种几何形状，可以利用这种有价值的电极材料的最大表面。在性能和生产率方面，细胞大小可以与传统的制备方法竞争。可以优化反应参数并轻松升级至更大的流通池。通过使用该电池，可以节省有机电转化过程中的起始原料。为了证明该特定电池的实用性，建立了精细化工和制药业重要组成部分的两次转化，其中包括有效而简单的后处理方案。
• Synthesis of 1,2,3-Triazole Substituted Isoxazoles<i>via</i>Copper (I) Catalyzed Cycloaddition
  作者：P. Venkata Ramana、A. Ram Reddy

  DOI：10.1002/jhet.837

  日期：2012.5

  containing N‐substituted 1,2,3‐triazoles (V) starting from various benzaldehydes (I) is reported. Benzaldehydes undergo oximation with hydroxylamine hydrosulfate. Later, chlorination followed by condensation with methylacetoacetate and the hydrolysis of the resulting ester afforded respective carboxylic acid (II), which on chlorination with PCl5 gave the corresponding acid chlorides (III). The coraboxylic

  据报道，从各种苯甲醛（I）开始，合成了一系列包含N-取代的1,2,3-三唑（V）的3,5-二取代的异恶唑-4-羧酸酯。苯甲醛与羟胺硫酸氢盐进行肟化反应。随后，氯化，然后与乙酰乙酸甲酯缩合，并将所得的酯水解，得到相应的羧酸（II），其在用PCl 5氯化后得到相应的酰氯（III）。炔丙基化时的钴氧酰氯（III）得到炔丙基酯（IV），点击反应这些得到标题化合物（V）。