4-碘-3-甲基-5-苯异噁唑 | 16114-53-7

• 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: 4-碘-3-甲基-5-苯异噁唑
• 英文名称: 4-iodo-3-methyl-5-phenylisoxazole
• 英文别名: 4-iodo-3-methyl-5-phenyl-isoxazole；3-Methyl-4-iod-5-phenyl-isoxazol；4-Iod-3-methyl-5-phenyl-isoxazol；3-Methyl-4-jod-5-phenylisoxazol；4-iodo-3-methyl-5-phenyl-1,2-oxazole
• CAS: 16114-53-7
• 化学式: C₁₀H₈INO
• mdl: MFCD03086126
• 分子量: 285.084
• InChiKey: RLZGZJOMCXKYIW-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 海关编码：
  2934999090
• 安全说明：
  S24/25
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Name:	4-Iodo-3-methyl-5-phenylisoxazole 97% Material Safety Data Sheet
Synonym:
CAS:	16114-53-7

Section 1 - Chemical Product MSDS Name:4-Iodo-3-methyl-5-phenylisoxazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16114-53-7	4-Iodo-3-methyl-5-phenylisoxazole	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16114-53-7: 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: yellow
Odor: odorless - slight odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 65 - 67 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: C10H8INO
Molecular Weight: 285.08

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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, hydrogen iodide, iodine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16114-53-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Iodo-3-methyl-5-phenylisoxazole - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 16114-53-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16114-53-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16114-53-7 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：

  4-碘-3-甲基-5-苯异噁唑 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  手性巯基乙酰胺在氧化应激的皮质神经元模型中显示组蛋白去乙酰化酶6的对映体选择性抑制和展示神经保护作用。

  摘要：

  基于巯基乙酰胺的配体已被设计为新型的组蛋白脱乙酰基酶（HDAC）抑制剂，可用于治疗神经退行性疾病。这些化合物的硫醇基团提供了与催化锌离子相互作用的关键结合元素，因此不同于更常用的基于异羟肟酸的锌结合基团。本文中，我们公开了一些取代的巯基乙酰胺的化学和生物学性质，目的是提高HDAC6同工型的选择性，同时保持类似于其异羟肟酸类似物的效价。发现向硫醇基团引入立体中心α对HDAC抑制剂效能具有相当大的影响。

  DOI：

  10.1002/cmdc.201100522
• 作为产物：
  描述：

  4-phenylbut-3-yn-2-one O-methyl oxime 在 N-碘代丁二酰亚胺 、 三甲基氯硅烷 作用下， 以 硝基甲烷 为溶剂， 反应 5.0h， 以86%的产率得到4-碘-3-甲基-5-苯异噁唑
  参考文献：
  名称：

  使用TMSCl-NCS在氯化环化反应中直接合成4-氯异恶唑的可 异构化（E / Z）-炔基-O-甲基肟†

  摘要：

  第一次，通过氯化环化反应，由（E / Z）-炔基-O-甲基肟直接以中等至优异的产率直接合成了4-氯异恶唑。该合成方法是在硝基甲烷溶剂中结合使用N-氯代琥珀酰亚胺（NCS）和三甲基氯硅烷（TMSCl），在其中原位生成氯（Cl 2）和盐酸（HCl）。此外，当N-溴代琥珀酰亚胺（NBS）和N分别使用-碘代琥珀酰亚胺（NIS）代替NCS。从制备炔基-O-甲基肟的步骤开始，由于（E）-异构体可在该条件下异构化和环化，因此本方法可提高制备4-卤代恶唑的总效率。

  DOI：

  10.1039/c6ra09396e

文献信息

• Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines
  作者：Wen-Bo Shen、Xin-Yu Xiao、Qing Sun、Bo Zhou、Xin-Qi Zhu、Juan-Zhu Yan、Xin Lu、Long-Wu Ye

  DOI：10.1002/anie.201610042

  日期：2017.1.9

  Platinum‐catalyzed formal [5+2] and [4+2] annulations of isoxazoles with heterosubstituted alkynes enabled the atom‐economical synthesis of valuable 1,3‐oxazepines and 2,5‐dihydropyridines, respectively. Importantly, this Pt catalysis not only led to unique reactivity dramatically divergent from that observed under Au catalysis, but also proceeded via unprecedented α‐imino platinum carbene intermediates

  铂催化异恶唑与杂取代炔烃的正式[5 + 2]和[4 + 2]环空反应分别实现了经济的合成有价值的1,3-氧杂氮杂和2,5-二氢吡啶。重要的是，这种Pt催化不仅导致与Au催化下观察到的独特反应性显着不同，而且还通过前所未有的α-亚氨基铂卡宾中间体进行了反应。
• Palladium-Catalyzed Cross-Coupling Reaction of Haloazoles with Phenylsulfonylacetonitrile
  作者：Takao Sakamoto、Yoshinori Kondo、Takashi Suginome、Setsuya Ohba、Hiroshi Yamanaka

  DOI：10.1055/s-1992-26163

  日期：——

  Condensation of halo-substituted 1,3-azoles (1,3-oxazoles, 1,3-thiazoles and imidazoles) with phenylsulfonylacetonitrile under basic conditions was promoted by catalytic action of tetrakis(triphenylphosphine)palladium(0) to give α-phenylsulfonyl-1,3-azoleacetonitriles. The adaptability of halogen atoms for the cross-coupling reaction was investigated. The reaction of 4-halo-1,2-azoles was also examined.

  在四(三苯基膦)钯(0)的催化作用下，经由卤代1,3-唑（1,3-噁唑、1,3-噻唑及咪唑）与苯磺酰丙腈在碱性条件下的缩合反应，合成了α-苯磺酰基-1,3-唑乙腈类化合物。探讨了卤素原子在交叉耦合反应中的适应性，并对4-卤代1,2-唑的反应进行了研究。
• The Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization:  An Efficient Synthesis of Valdecoxib
  作者：Jesse P. Waldo、Richard C. Larock

  DOI：10.1021/jo701942e

  日期：2007.12.1

  A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.

  大量官能取代的 2-alkyn-1-one O-甲基肟在温和的反应条件下在 ICl 存在下环化，以中等至极好的收率得到相应的 4-碘异恶唑。所得的 4-碘异恶唑经过各种钯催化反应生成 3,4,5-三取代的异恶唑，包括伐地考昔。
• Design, Synthesis, and Biological Evaluation of Nucleozin Sulfonyl Piperazine Derivatives as Anti-influenza A Virus inhibitors
  作者：Jun Chen、Shuchen Pei、Junlin Chen、Jinhua Yang、Lin Lai、Xiang Huang、Mingxin Xu

  DOI：10.2174/1570178619666220919102545

  日期：2022.9.19

  antivirals. In this study, a series of sulfonyl piperazine nucleozin derivatives were designed and synthesized, and their in vitro anti-influenza activity was evaluated. Many of these compounds exhibited moderate to good anti-influenza activity against influenza A. Among these, 6d, 6g, 6h, 6i, and 6j exhibited better activity than ribavirin. 2,3-dichlorobenzene substituted analogue 6i displayed the most remarkable

  甲型流感病毒通过重组和耐药突变体的产生引起了世界范围内的流行和大流行，这导致迫切需要开发新型抗病毒药物。本研究设计合成了一系列磺酰基哌嗪核苷衍生物，并对其体外抗流感活性进行了评价。许多这些化合物对甲型流感病毒表现出中等至良好的抗流感活性。其中，6d、6g、6h、6i 和 6j 表现出比利巴韦林更好的活性。2,3-二氯苯取代的类似物6i显示出最显着的体外抗甲型流感活性。所有衍生物对MDCK细胞均无明显的细胞生长抑制作用。
• Synthesis of 4-isoxazoleboronic acids: A new route to 4-isoxazolones
  作者：Augusto Cogoli、Paolo Grünanger

  DOI：10.1016/s0022-328x(00)92400-8

  日期：1967.7