3-(4-氟苯基)-5-甲基-4-异恶唑羧酸 | 1736-21-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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-(4-氟苯基)-5-甲基-4-异恶唑羧酸
• 中文别名: 3-(4-氟苯基)-5-甲基-异噁唑-4-甲酸；3-(4-氟苯基)-5-甲基-4-异噁唑羧酸；3-(4-氟苯基)-5-甲基异恶唑-4-羧酸
• 英文名称: 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylic acid
• 英文别名: 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid
• CAS: 1736-21-6
• 化学式: C₁₁H₈FNO₃
• mdl: MFCD03407356
• 分子量: 221.188
• InChiKey: PDEGBONVUJDOFN-UHFFFAOYSA-N

物化性质

• 熔点：
  198-202 °C
• 沸点：
  361.6±37.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  0-10°C；请避免加热。

SDS

Name:	3-(4-Fluorophenyl)-5-methyl-4-isoxazolecarboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	1736-21-6

Section 1 - Chemical Product MSDS Name:3-(4-Fluorophenyl)-5-methyl-4-isoxazolecarboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1736-21-6	3-(4-Fluorophenyl)-5-methyl-4-isoxazol	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# 1736-21-6: 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
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 202 - 203 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: C11H8FNO3
Molecular Weight: 221.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1736-21-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(4-Fluorophenyl)-5-methyl-4-isoxazolecarboxylic acid - 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# 1736-21-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1736-21-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1736-21-6 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：

  3-(4-氟苯基)-5-甲基-4-异恶唑羧酸 在 sodium tetrahydroborate 、 lithium hydroxide monohydrate 、 水 、 sodium hydride 、 N,N'-羰基二咪唑 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 67.5h， 生成 巴米沙尼
  参考文献：
  名称：

  (1aR,12bS)-8-cyclohexyl-11-fluoro-N-((1-methylcyclopropyl)sulfonyl)-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,2b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide for use in treating HCV

  摘要：

  该发明涉及一种包含该化合物及/或其药用盐的给药单元，以及包括该给药单元的包装。

  公开号：

  EP2792360A1
• 作为产物：
  描述：

  Methyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate 在 盐酸 、 溶剂黄146 作用下， 反应 72.0h， 生成 3-(4-氟苯基)-5-甲基-4-异恶唑羧酸
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives

  摘要：

  A series of unique 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides have been prepared which exhibit, in both greenhouse and field studies, significant preemergent and postemergent herbicidal activity in the grams per hectare range against broadleaf and narrowleaf weeds. The key step in the formation of the fully substituted isoxazole ring 2 is 1,3 dipolar cycloaddition of a haloalkyl-substituted acetylenic ester and a nitrile oxide intermediate. The 3-aryl-5-(halo alkyl)-4-isoxazolecarboxylate esters 2 are converted to isoxazole-4-carboxamide herbicides 5 and 6, secondary amides 7, and amino acid derivatives 8. Greatest activity was observed with compounds having a combination of three substituents: a substituted phenyl ring in the 3-position, a primary or secondary carboxamide in the 4-position, and a difluorochloromethyl group in the, 5-position of the isoxazole ring.

  DOI：

  10.1021/jf00049a040

文献信息

• Isoxazolecarboxamide derivatives
  申请人：Recordati, S.A., Chemical and Pharmacueticals Company

  公开号：US06365591B1

  公开（公告）日：2002-04-02

  The invention relates to novel N-(substituted phenyl)-N′-[&ohgr;-(3-substituted phenyl-4-isoxazolecarbonylamino)alkyl]piperazines, their N-oxides, and pharmaceutically acceptable salts thereof. The compounds are endowed with enhanced selectivity for alpha1-adrenergic receptors and a low activity in lowering blood pressure. The compounds are useful in the treatment of obstructive syndromes of the lower urinary tract, including benign prostatic hyperplasia (BPH), and in the treatment of lower urinary tract symptoms (LUTS) and neurogenic lower urinary tract dysfunction (NLUTD), and other conditions.

  该发明涉及新型N-(取代苯基)-N′-[ω-(3-取代苯基-4-异噁唑甲酰胺)烷基]哌嗪，它们的N-氧化物以及其药用可接受的盐。这些化合物具有增强的α1-肾上腺素受体选择性和降低血压活性较低。这些化合物在治疗下尿路梗阻综合征，包括良性前列腺增生（BPH），以及治疗下尿路症状（LUTS）和神经源性下尿路功能障碍（NLUTD）等疾病方面具有用途。
• Monodentate Palladium Complexes Bearing Abnormal and Normal Carbene Ligands with a Formally Identical Steric Environment
  作者：Chun-Hung Ke、Bing-Chiuan Kuo、Debkumar Nandi、Hon Man Lee

  DOI：10.1021/om4004219

  日期：2013.9.9

  environment around the metal center. The corresponding ligand precursors were prepared via the key steps based on Pd-catalyzed direct C–H arylation between imidazo[1,2-a]pyridine and aryl bromides and Cu-catalyzed C–N coupling reactions between benzoimidazole and aryl bromides. The new complexes were characterized by 1D and 2D NMR spectroscopy, X-ray crystallography, and elemental analysis. The isomeric

  我们报告了一系列具有单齿异常和正常卡宾配体的新型异构Pd（II）配合物，在金属中心周围具有形式上完全相同的空间环境。相应的配体前体是通过基于咪唑并[1,2- a]之间的Pd催化的直接CH芳基化的关键步骤制备的]吡啶和芳基溴化物以及铜催化的苯并咪唑与芳基溴化物之间的C–N偶联反应。通过1D和2D NMR光谱，X射线晶体学和元素分析对新配合物进行了表征。配体的同分异构体对在其空间性质之间显示出较小的差异，这可以通过计算其掩埋体积来检查。发现异常卡宾Pd（II）配合物在催化Mizoroki–Heck偶联，直接C–H芳基化和脱羧偶联反应方面更有效，这显然可以归因于异常卡宾配体的更强的电子捐赠作用。
• Synthesis, Identification, and Structure–Activity Relationship Analysis of GATA4 and NKX2-5 Protein–Protein Interaction Modulators
  作者：Mikael Jumppanen、Sini M. Kinnunen、Mika J. Välimäki、Virpi Talman、Samuli Auno、Tanja Bruun、Gustav Boije af Gennäs、Henri Xhaard、Ingo B. Aumüller、Heikki Ruskoaho、Jari Yli-Kauhaluoma

  DOI：10.1021/acs.jmedchem.9b01086

  日期：2019.9.12

  cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective

  转录因子GATA4和NKX2-5直接相互作用并协同激活几种心脏基因和牵张诱导的心肌肥大。以前，我们将苯基异恶唑羧酰胺1确定为命中化合物，该化合物可抑制GATA4-NKX2-5转录协同作用。在此，通过合成和表征220个衍生物和与结构相关的化合物，探索了1分子结构周围的化学空间。除了协同转录激活，还评估了所选化合物对GATA4和NKX2-5转录活性的影响以及潜在的细胞毒性。结构-活性关系（SAR）分析表明，南部的芳族异恶唑取代基可调节对GATA4-NKX2-5转录协同的抑制作用。而且，对GATA4转录活性的抑制与细胞活力的降低有关。总之，综合的SAR分析和数据分析成功地确定了GATA4-NKX2-5转录协同作用的有效和选择性抑制剂，并揭示了对其重要的结构特征。
• PROCESS FOR THE PREPARATION OF ISOXAZOLYL- METHOXY NICOTINIC ACIDS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130102778A1

  公开（公告）日：2013-04-25

  The present invention relates to a process for the preparation of a compound of formula (I) wherein R 1 and R 2 are as defined herein, which is useful as an intermediate in the preparation of active pharmaceutical compounds.

  本发明涉及一种制备式(I)化合物的方法，其中R1和R2如本文所定义，该方法在制备活性药物化合物中作为中间体是有用的。
• [EN] PROCESS FOR THE PREPARATION OF ISOXAZOLYL-METHOXY-NICOTINIC ACIDS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDES ISOXAZOLYL-MÉTHOXY-NICOTINIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013057123A1

  公开（公告）日：2013-04-25

  The present invention relates to a process for the preparation of a compound of formula (I) which is useful as an intermediate in the preparation of active pharmaceutical compounds from a compound of formula (IV) wherein R1 and R2 are as defined herein,.

  本发明涉及一种用于制备式(I)化合物的方法，该方法在制备活性药物化合物时作为中间体使用，所述活性药物化合物由式(IV)化合物制备而来，其中R1和R2如本文所定义。

表征谱图