3-溴-5-苯基异噁唑 | 10557-74-1

• 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-5-苯基异噁唑
• 中文别名: 3-溴-5-苯基异恶唑
• 英文名称: 3-bromo-5-phenylisoxazole
• 英文别名: 3-bromo-5-phenyl-isoxazole；3-Brom-5-phenyl-isoxazol；3-Bromo-5-fenilisossazolo；3-Brom-5-phenylisoxazol；3-Bromo-5-phenyl-1,2-oxazole
• CAS: 10557-74-1
• 化学式: C₉H₆BrNO
• 分子量: 224.057
• InChiKey: SMWZGZIZOHNWBH-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73℃
• 沸点：
  120-121 °C(Press: 1 Torr)
• 密度：
  1.524±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  2

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-phenyl-1,2-oxazole
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-phenyl-1,2-oxazole
CAS number: 10557-74-1

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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: C9H6BrNO
Molecular weight: 224.1

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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-5-苯基异噁唑 在 magnesium 作用下， 生成 5-苯基异噁唑
  参考文献：
  名称：

  Cabiddu,S.; Solinas,V., Gazzetta Chimica Italiana, 1969, vol. 99, p. 1107 - 1114

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙炔 在 ammonium hydroxide 、 盐酸羟胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 3-溴-5-苯基异噁唑
  参考文献：
  名称：

  Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper(I) Alkynes and Dihaloformaldoximes

  摘要：

  A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.

  DOI：

  10.1021/ol503008t

文献信息

• 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。
• Process for the preparation of 3,5-disubstituted isoxazoles
  申请人：Zambon S.p.A.

  公开号：US04772719A1

  公开（公告）日：1988-09-20

  A novel process for the preparation of 3-bromo- and 3-chloro-5-substituted isoxazoles is provided. Dibromo- or dichloro-formaldoxime is reacted with an excess of an 1-alkyne derivative of the formula R--C.tbd.CH where R is hydrogen, phenyl or 1-6 C alkyl optionally substituted by halogen, OH, OR', CHO, COR', COOR', CONH.sub.2, CONR'R" or NHCOR' where, in turn, R' and R", which may be the same or different, are a 1-6 C alkyl or haloalkyl, in the presence of (i) at least an equimolecular amount, with respect to the dibromo- or dichloro-formaldoxime, of an alkaline base selected from the class consisting of sodium and potassium carbonate and bicarbonate and (ii) an inert solvent in which the 1-alkyne is soluble at room temperature.

  提供了一种制备3-溴-和3-氯-5-取代异噁唑的新工艺。在（i）至少等摩尔量的碱性碳酸钠和碳酸氢钾的类别中选择碱性碱，与二溴甲酰肟或二氯甲酰肟一起，在惰性溶剂中，在室温下与化学式为R-C.tbd.CH的1-炔基衍生物的过量反应，其中R为氢，苯基或1-6 C烷基，可选地被卤素，OH，OR'，CHO，COR'，COOR'，CONH.sub.2，CONR'R"或NHCOR'取代，其中R'和R"可以相同或不同，是1-6 C烷基或卤代烷基。
• Fusco; Rossi, Chemistry and industry, 1957, p. 1650
  作者：Fusco、Rossi

  DOI：——

  日期：——
• CARR J. B.; DURHAM H. G.; HASS D. K., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 7, 934-939
  作者：CARR J. B.、 DURHAM H. G.、 HASS D. K.

  DOI：——

  日期：——
• CHIARINO D.; NAPOLETANO M.; SALA A., J. HETEROCYCL. CHEM., 24,(1987) N 1, 45-46
  作者：CHIARINO D.、 NAPOLETANO M.、 SALA A.

  DOI：——

  日期：——