5-氨基-3-甲基异恶唑-4-甲酸乙酯 | 25786-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-3-甲基异恶唑-4-甲酸乙酯
• 中文别名: 3-甲基-5-氨基-4-异噁唑羧酸乙酯；5-氨基-3-甲基异噁唑-4-羧酸乙酯
• 英文名称: 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester
• 英文别名: ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate；ethyl 5-amino-3-methyl-4-isoxazole carboxylate；ethyl 5-amino-3-methyl-isoxazole-4-carboxylate；5-amino-3-methyl-4-ethoxycarbonylisoxazole；5-amino-3-methyl-isoxazole-4-carboxylic acid ethyl ester；5-Amino-3-methyl-isoxazol-4-carbonsaeure-aethylester
• CAS: 25786-72-5
• 化学式: C₇H₁₀N₂O₃
• mdl: MFCD03820571
• 分子量: 170.168
• InChiKey: ULIKRPZEQZFBPS-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  287.0±35.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-3-methyl-isoxazole-4-carboxylic acid ethyl ester
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Amino-3-methyl-isoxazole-4-carboxylic acid ethyl ester
CAS number: 25786-72-5

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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.

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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.

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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.

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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.
Storage: Store in closed vessels, under −20◦C.

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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.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H10N2O3
Molecular weight: 170.2

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氨基-3-甲基异恶唑-4-甲酸乙酯 在 盐酸 、 sodium nitrite 、 次磷酸 作用下， 以 水 为溶剂， 反应 1.25h， 以27%的产率得到3-甲基异唑-4-甲酸乙酯
  参考文献：
  名称：

  Ryng; Szostak, Polish Journal of Chemistry, 2009, vol. 83, # 5, p. 887 - 893

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基乙酰乙酸乙酯 在 吡啶 、 盐酸 、 乙醇 、 羟胺 作用下， 生成 5-氨基-3-甲基异恶唑-4-甲酸乙酯
  参考文献：
  名称：

  异恶唑酮。第六部分 5-氨基异恶唑的氢化。嘧啶的新合成

  摘要：

  DOI：

  10.1039/jr9540000665

文献信息

• Base-induced ring cleavage of 4-functionalized-3-unsubstituted isoxazoles. Synthesis of 5-aminoazoles and 4-cyanoazoles
  作者：A. Alberola、L. F. Antolin、A. M. Gonzalez、M. A. Laguna、F. J. Pulido

  DOI：10.1002/jhet.5570230414

  日期：1986.7

  The base-induced ring cleavage of 4-nitro-(Ia), 4-ethoxycarbonyl- (Ib) and 4-acetyl-5-methylisoxazole (Ic) and the conversion of the resulting β-cyanoenolates and β-enaminonitriles into 5-aminoazoles and 4-cyanoazoles was studied.

  4-硝基-（Ia），4-乙氧基羰基-（Ib）和4-乙酰基-5-甲基异恶唑（Ic）的碱诱导的环裂解以及所得的β-氰基烯酸酯和β-烯腈转化为5-氨基唑并研究了4-氰基唑。
• [EN] SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE NADPH OXYDASE
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018203298A1

  公开（公告）日：2018-11-08

  The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

  本申请涉及取代的融合杂环芳基和杂环化合物，用作烟酰胺腺嘌呤二核苷酸磷酸酶抑制剂（NADPH氧化酶抑制剂），其制备方法，包含这些化合物的药物组合物，以及这些化合物或组合物在治疗或预防由NADPH氧化酶介导的各种疾病、症状和/或障碍中的用途。 (分子式I)
• [EN] PESTICIDALLY ACTIVE PYRIDYL- AND PYRIMIDYL- SUBSTITUTED THIAZOLE AND THIADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE THIAZOLE ET DE THIADIAZOLE SUBSTITUÉS PAR PYRIDYLE ET PYRIMIDYLE, ACTIFS EN TANT QUE PESTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013156431A1

  公开（公告）日：2013-10-24

  Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula (I) can be used as agrochemical active ingredients and can be prepared in a manner known per se.

  式（I）的化合物，其中取代基如权利要求1中定义的那样，以及式（I）的所有立体异构体和互变异构体形式的农药可接受盐可以用作农药活性成分，并且可以按照已知的方法制备。
• Keggin Heteropolyacid Catalyzed Synthesis of Isoxazolo- [5,4-d]pyrimidine-4,6(5H,7H)-diones at Room Temperature
  作者：Fatemeh F. Bamoharram、Mina Roshani、Majid M. Heravi、Masoumeh Mahdavi、Ali Javid、Jalal Sh. Emampour

  DOI：10.1002/cjoc.201090180

  日期：——

  Isoxazolo[5,4‐d]pyrimidine‐4,6(5H,7H)diones 2a–2f have been synthesized from the reaction of ethyl 5‐amino‐3‐methyl‐4‐isoxazole carboxylate (1) with aryl isocyanates in the presence of Keggin heteropolyacid H3[PW12O40] as a green solid acid catalyst at room temperature in a one‐pot process in good yields.

  异恶唑并[5,4 - d ]嘧啶-4,6（5 H，7 H）二酮2a - 2f是由5-氨基-3-甲基-4-甲基异恶唑羧酸乙酯（1）与异氰酸芳基酯反应合成的在Keggin杂多酸H 3 [PW 12 O 40 ]作为绿色固体酸催化剂的存在下，在室温下通过一锅法获得高收率。
• 5-Amino-3-methyl-Isoxazole-4-carboxylic Acid as a Novel Unnatural Amino Acid in the Solid Phase Synthesis of α/β-Mixed Peptides
  作者：Urszula Bąchor、Agnieszka Lizak、Remigiusz Bąchor、Marcin Mączyński

  DOI：10.3390/molecules27175612

  日期：——

  The hybrid peptides consisting of α and β-amino acids show great promise as peptidomimetics that can be used as therapeutic agents. Therefore, the development of new unnatural amino acids and the methods of their incorporation into the peptide chain is an important task. Here, we described our investigation of the possibility of 5-amino-3-methyl-isoxazole-4-carboxylic acid (AMIA) application in the

  由α和β-氨基酸组成的杂合肽作为可用作治疗剂的肽模拟物显示出巨大的前景。因此，开发新的非天然氨基酸及其掺入肽链的方法是一项重要任务。在这里，我们描述了我们对 5-氨基-3-甲基-异恶唑-4-羧酸 (AMIA) 在固相肽合成中的应用可能性的调查。这种具有多种生物活性的新型非天然 β-氨基酸使用不同的反应条件（包括经典和超声搅拌固相合成）成功地与树脂结合的肽偶联。所有合成的化合物均通过串联质谱进行表征。