2-碘-4-甲氧基苯基胺 | 191348-14-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-碘-4-甲氧基苯基胺
• 中文别名: 2-碘-4-甲氧基苯胺；4-氨基-3-碘苯甲醚
• 英文名称: 2-iodo-4-methoxylaniline
• 英文别名: 2-iodo-4-methoxyaniline；2-iodo-4-methoxybenzenamine；4-amino-3-iodoanisole；2-Iodo-4-methoxyphenylamine
• CAS: 191348-14-8
• 化学式: C₇H₈INO
• mdl: MFCD07776739
• 分子量: 249.051
• InChiKey: ASINPZWBVCLVDK-UHFFFAOYSA-N

物化性质

• 沸点：
  305.0±27.0 °C(Predicted)
• 密度：
  1.807±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2922299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Iodo-4-methoxyaniline
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: 2-Iodo-4-methoxyaniline
CAS number: 191348-14-8

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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: C7H8INO
Molecular weight: 249.0

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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 Iodide.

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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

制备方法与用途

2-碘-4-甲氧基苯胺在医药和印染领域均有广泛的应用，市场需求量巨大。该化合物可用于制备苯并噻唑类化合物。苯并噻唑是一类重要的有机化合物，因为其核心骨架——苯并噻唑，在医药、化工等领域具有重要应用价值。此外，由于2号位的C-H键较为活泼，利用这一特性已经发展出了许多合成2-取代苯并噻唑化合物的方法，使其成为合成此类化合物的重要原料之一。

反应信息

• 作为反应物：
  描述：

  2-碘-4-甲氧基苯基胺 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 三(三甲基硅基)硅烷 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 58.0h， 生成 褪黑素
  参考文献：
  名称：

  Efficient Route to the Pineal Hormone Melatonin by Radical-Based Indole Synthesis

  摘要：

  The hormone melatonin, which is known to have a range of important biological effects, has been prepared in a high-yielding route that features formation of the indole nucleus by radical cyclization. Mediation of the radical cyclization by tristrimethylsilylsilane (TTMSS) is more efficient than by N-ethylpiperidine hypophosphite.

  DOI：

  10.1081/scc-120024751
• 作为产物：
  描述：

  甲氧苯胺 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-碘-4-甲氧基苯基胺
  参考文献：
  名称：

  一个涉及一个锅中六个反应的新型自序列反应网络：由芳香族酮和苯胺合成取代的苯并噻唑

  摘要：

  使用简单易得的芳香族酮和苯胺作为起始原料，可以通过一个新颖的自序反应网络构建2-酰基苯并噻唑，该网络在一个罐中组装六个反应。该反应网络不仅为构建复杂分子提供了一种新颖的方法，而且为逻辑自组织合成提供了一个典型的例子。

  DOI：

  10.1021/ol400029t

文献信息

• MACROCYCLIC COMPOUNDS AND THEIR USE AS KINASE INHIBITORS
  申请人：Combs Andrew Paul

  公开号：US20090286778A1

  公开（公告）日：2009-11-19

  The present invention relates to macrocyclic compounds of Formula I: or pharmaceutically acceptable salts thereof or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are JAK/ALK inhibitors useful in the treatment of JAK/ALK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及以下化学式I的大环化合物： 或其药用可接受盐或季铵盐，其中所述成员在此提供，并且它们的组成物和使用方法，这些JAK/ALK抑制剂在治疗JAK/ALK相关疾病中有用，例如炎症和自身免疫性疾病以及癌症。
• Discovery of Aminopiperidine Indoles That Activate the Guanine Nucleotide Exchange Factor SOS1 and Modulate RAS Signaling
  作者：Jason R. Abbott、Timothy R. Hodges、R. Nathan Daniels、Pratiq A. Patel、J. Phillip Kennedy、Jennifer E. Howes、Denis T. Akan、Michael C. Burns、Jiqing Sai、Tammy Sobolik、Yugandhar Beesetty、Taekyu Lee、Olivia W. Rossanese、Jason Phan、Alex G. Waterson、Stephen W. Fesik

  DOI：10.1021/acs.jmedchem.8b00360

  日期：2018.7.26

  Deregulated RAS activity, often the result of mutation, is implicated in approximately 30% of all human cancers. Despite this statistic, no clinically successful treatment for RAS-driven tumors has yet been developed. One approach for modulating RAS activity is to target and affect the activity of proteins that interact with RAS, such as the guanine nucleotide exchange factor (GEF) son of sevenless

  RAS 活性失调通常是突变的结果，约 30% 的人类癌症与此有关。尽管有这一统计数据，但尚未开发出针对 RAS 驱动肿瘤的临床成功治疗方法。调节 RAS 活性的一种方法是靶向并影响与 RAS 相互作用的蛋白质的活性，例如七同源物 1 (SOS1) 的鸟嘌呤核苷酸交换因子 (GEF)。在这里，我们报告了吲哚系列化合物的构效关系 (SAR)。使用基于结构的设计，我们系统地探索了吲哚核、悬垂氨基酸部分以及连接这两个片段的连接单元的取代模式。一流的化合物可在体外以亚微摩尔浓度激活核苷酸交换过程，提高 HeLa 细胞中活性 RAS-GTP 的水平，并引发丝裂原激活蛋白激酶 - 细胞外调节激酶 (MAPK-ERK) 通路中的信号传导变化，导致较高化合物浓度下pERK1/2 T202/Y204蛋白水平降低。
• FUSED AMINO PYRIDINE AS HSP90 INHIBITORS
  申请人：Cai Xiong

  公开号：US20080234314A1

  公开（公告）日：2008-09-25

  The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.

  本发明涉及含有融合氨基吡啶核的HSP90抑制剂，可用作HSP90的抑制剂，以及它们在治疗HSP90相关疾病和紊乱，如癌症、自身免疫疾病或神经退行性疾病中的用途。
• Selective Construction of 2-Substituted Benzothiazoles from <i>o</i>-Iodoaniline Derivatives S₈ and <i>N</i>-Tosylhydrazones
  作者：Yubing Huang、Peiqi Zhou、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.7b03118

  日期：2018.2.16

  Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom

  已经实现了通过铜促进的[3 +1 + 1]型环化反应，由邻碘苯胺衍生物S 8和N-甲苯磺酰zone选择性构建2-取代的苯并噻唑。在该方案中，可以通过改变反应体系来调节N-甲苯磺酰hydr上的碳原子以构建苯并噻唑。此外，该转化实现了多个碳-杂原子键的构建。
• Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[<i>b</i>]thiazinones from 2-iodophenylcinnamamides and potassium sulfide
  作者：Wenjuan Liu、Hao Min、Xiaoming Zhu、Guobo Deng、Yun Liang

  DOI：10.1039/c7ob02585h

  日期：——

  An efficient and practical procedure for the synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from easily available 2-iodophenylcinnamamides and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds via electrophilic addition, followed by dehydrogenation and reduction to give 2-benzyl benzo[b]thiazinones. Furthermore, 2-benzylidenebenzo[b]thiazinones

  已经开发了一种由容易获得的2-碘苯基肉桂酰胺和硫化钾合成2-苄基和2-亚苄基取代的苯并[ b ]噻嗪酮的有效且实用的方法。在DBU的存在下，反应通过亲电加成进行，然后脱氢并还原，得到2-苄基苯并[ b ]噻嗪酮。此外，在不添加DBU的情况下，以中等至良好的产率获得了2-亚苄基苯并[ b ]噻嗪酮。