(3-溴异恶唑-5-基)甲醇 | 25742-00-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: (3-溴异恶唑-5-基)甲醇
• 中文别名: 3-溴-5-羟甲基异恶唑
• 英文名称: (3-bromoisoxazol-5-yl)methanol
• 英文别名: (3-bromo-isoxazol-5-yl)-methanol；3-bromo-5-hydroxymethylisoxazole；3-bromo-isoxazol-5-yl-methanol；(3-bromo-1,2-oxazol-5-yl)methanol
• CAS: 25742-00-1
• 化学式: C₄H₄BrNO₂
• 分子量: 177.985
• InChiKey: IPMKBMJCEWOFOB-UHFFFAOYSA-N

物化性质

• 沸点：
  93-95 °C(Press: 1 Torr)
• 密度：
  1.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-hydroxymethylisoxazole
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: 3-Bromo-5-hydroxymethylisoxazole
CAS number: 25742-00-1

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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.
Store in closed vessels, refrigerated.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H4BrNO2
Molecular weight: 178

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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, hydrogen bromide.

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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：

  (3-溴异恶唑-5-基)甲醇 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 3-溴异恶唑-5-甲酸
  参考文献：
  名称：

  6-取代的十氢异喹啉-3-羧酸AMPA受体拮抗剂的结构活性研究。2.远端酸生物等排体取代，绝对立体化学偏好和体内活性的影响。

  摘要：

  我们探索了一系列十氢异喹啉-3-羧酸中的兴奋性氨基酸拮抗剂活性，并在该系列中发现了有效的选择性AMPA拮抗剂（3SR，4aRS，6RS，8aRS）-6-（2-（1H -四唑-5-基）乙基）十氢异喹啉-3-羧酸（1）。在本文中，我们研究了该系列化合物中AMPA拮抗剂活性的构效关系。我们已经表明1具有最佳的立体化学阵列，并且AMPA拮抗剂活性对于将四唑与双环核分开的二碳间隔基而言是最大的。在本文中，我们探讨了改变远端酸的作用以及许多类似物的绝对立体化学偏好。我们研究了各种不同的酸性生物异构体，包括五元杂环酸，例如四唑，1,2,4-三唑和3-异恶唑酮；羧酸，膦酸和磺酸；和酰基磺酰胺。对大鼠皮质组织中的化合物抑制AMPA（[3H] AMPA），NMDA（[3H] CGS 19755）和海藻酸（[3H] kainic acid）受体选择性放射性配体结合的能力及其功能进行了评估抑制由AMPA（40 microM），NMDA（40

  DOI：

  10.1021/jm950913h
• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 2-丙炔-1-醇 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 以68%的产率得到(3-溴异恶唑-5-基)甲醇
  参考文献：
  名称：

  通过功能化卤素肟的区域选择性反应合成5-（氟烷基）异恶唑结构单元。

  摘要：

  报道了从官能化的卤代肟开始合成5-氟烷基取代的异恶唑的综合研究。开发了无罐的CF3取代烯烃和带有酯，溴，氯甲基和受保护氨基的卤代肟的无金属[3 + 2]环加成反应，用于制备5-三氟甲基异恶唑。以区域选择性的方式以高达130g的规模以良好或优异的产率获得了目标3，5-二取代的衍生物。通过相应的5-羟甲基或5-甲酰基衍生物的后期脱氧氟化分别合成5-氟甲基-异氟唑和5-二氟甲基异恶唑，然后通过无金属环合肟和炔丙醇来制备5-氟甲基异恶唑。发现在5-溴甲基衍生物中基于亲核取代的替代方法对于制备5-氟甲基异恶唑更方便。将异恶唑-5-甲醛与Ruppert-Prakash试剂的反应用于制备（β，β，β-三氟-α-羟乙基）异恶唑。通过多链制备侧链官能化的单，二和三氟甲基异恶唑，例如，ABT-418和ESI-09的氟化类似物，表明了所描述方法的实用性。

  DOI：

  10.1021/acs.joc.9b02264

文献信息

• [EN] AZAINDAZOLE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS AZAINDAZOLE EN TANT QU'ANTAGONISTES DES RÉCEPTEURS CCR1
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010036632A1

  公开（公告）日：2010-04-01

  Disclosed are compounds of the formula (I), useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of CCR1 including autoimmune diseases, such as rheumatoid arthritis and multiple sclerosis. Also disclosed are methods of making and methods of using same.

  公开的是化合物的公式（I），用于治疗通过CCR1活性介导或维持的多种疾病和疾病，包括自身免疫性疾病，如风湿性关节炎和多发性硬化症。还公开了制备方法和使用方法。
• The Chemistry of Pseudomonic Acid. Part 14. Synthesis and In Vivo Biological Activity of Heterocyclyl Substituted Oxazole Derivatives.
  作者：N. J. P. BROOM、J. S. ELDER、P. C. T. HANNAN、J. E. PONS、P. J. O''HANLON、G. WALKER、J. WILSON、P. WOODALL

  DOI：10.7164/antibiotics.48.1336

  日期：——

  heterocyclyl substituted oxazole. Derivatives in which the heterocycle was thiophene, furan, pyridine, or isoxazole showed good antibacterial potency and were further evaluated in vivo. Both pharmacokinetic parameters and oral activity against an experimental intraperitoneal sepsis were superior to results obtained from previously described pseudomonic acid A derivatives.

  已制备了含有杂环基取代的恶唑的假单酸A的半合成类似物。杂环为噻吩，呋喃，吡啶或异恶唑的衍生物显示出良好的抗菌效力，并在体内进行了进一步评估。药代动力学参数和针对实验性腹膜内脓毒症的口服活性均优于从先前描述的假单酸A衍生物获得的结果。
• 1,3-Dipolar cycloaddition synthesis of 3-bromo-5-substituted isoxazoles, useful intermediates for the preparation of pharmacologically active compounds
  作者：D. Chiarino、M. Napoletano、A. Sala

  DOI：10.1002/jhet.5570240109

  日期：1987.1

  monosubstituted acetylenic derivatives 4 to give 3-bromo-5-substituted isoxazoles 5 in high yield. The experimental conditions necessary to overcome difficulties such as the low reactivity of acetylenic dipolarophiles and the high tendency to dimerization of bromonitrile oxide 2, are discussed; the regioselectivity of this 1,3-dipolar cycloaddition is also studied. The obtained improvements in the synthesis of

  Bromonitrile氧化物2，从容易获得的二溴甲醛肟生成1，与单取代的炔属衍生物进行反应4，得到3-溴-5-异恶唑取代的5以高收率。讨论了克服困难的条件，例如乙炔双极性亲和剂的低反应性和溴代腈氧化物2的二聚化趋势高。还研究了这种1，3-偶极环加成反应的区域选择性。据报道在某些药理活性化合物的合成中获得的改进。
• 一类作为吲哚胺2,3-双加氧酶抑制剂的螺环类化合物
  申请人：齐鲁制药有限公司

  公开号：CN114685341A

  公开（公告）日：2022-07-01

  本发明提供了具有螺环结构的可作为吲哚胺2，3‑双加氧酶(IDO)抑制剂的化合物，含有所述化合物的药物组合物，利用所述化合物制备治疗增殖性疾病、感染性疾病、免疫相关疾病和/或炎性疾病的药物的应用。
• Cabiddu,S.; Solinas,V., Gazzetta Chimica Italiana, 1969, vol. 99, p. 1107 - 1114
  作者：Cabiddu,S.、Solinas,V.

  DOI：——

  日期：——