3-氟-4-碘苯胺 | 656-66-6

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氟-4-碘苯胺
• 中文别名: 4-溴-3-氟苯胺
• 英文名称: 3-fluoro-4-iodoaniline
• CAS: 656-66-6
• 化学式: C₆H₅FIN
• 分子量: 237.015
• InChiKey: KUVVJHBHRIXJKI-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  273.7±25.0 °C(Predicted)
• 密度：
  2.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 海关编码：
  2921420090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  冷藏保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluoro-4-iodoaniline
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluoro-4-iodoaniline
CAS number: 656-66-6

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H5FIN
Molecular weight: 237.0

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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 fluoride, 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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (3-Fluoro-4-iodoaniline)

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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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氟-4-碘苯胺 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 nickel(II) chloride hexahydrate 、 四甲基乙二胺 、 potassium carbonate 、 lithium trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 69.5h， 生成 (S)-methyl 3-(4-(cyclopropylbuta-1,3-diyn-1-yl)-3-fluorophenyl)oxazolidin-2-one-5-carboxylate
  参考文献：
  名称：

  LpxC抑制剂：设计，合成和生物评价恶唑烷酮作为革兰氏阴性抗菌剂。

  摘要：

  在本文中，我们报告了一种支架跳跃方法，以鉴定具有锌结合头基的新支架。结构信息用于提供基于恶唑烷酮的新型LpxC抑制剂。特别地，最有效的化合物23j显示出低的流出比，对大肠杆菌LpxC酶的纳摩尔效价和对大肠杆菌和肺炎克雷伯菌的极好的抗菌活性。计算对接用于预测23j与大肠杆菌LpxC之间的相互作用，这表明与C207和C63的相互作用有助于产生强活性。这些结果为下一代LpxC抑制剂的设计提供了新的见识。

  DOI：

  10.1021/acsmedchemlett.6b00057
• 作为产物：
  描述：

  3-氟苯胺 在 iron(III) chloride 、 N-碘代丁二酰亚胺 、 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 作用下， 反应 2.0h， 以62%的产率得到3-氟-4-碘苯胺
  参考文献：
  名称：

  铁（III）催化的N-碘代琥珀酰亚胺活化对芳烃的高度区域选择性碘化

  摘要：

  已经开发了铁（III）催化的用于芳烃的快速和高度区域选择性碘化的方法。使用由氯化铁（III）原位生成的强力路易斯酸，三氟化铁（III）和易于获得的基于三氟化物的离子液体，可以在宽范围的温和条件下活化N-碘代琥珀酰亚胺（NIS）和有效的碘化作用底物，包括生物活性化合物和分子显像剂。

  DOI：

  10.1021/acs.orglett.5b02345

文献信息

• Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions
  作者：Vishal Kandathil、Ramesh B. Dateer、B. S. Sasidhar、Shivaputra A. Patil、Siddappa A. Patil

  DOI：10.1007/s10562-018-2369-5

  日期：2018.6

  in aryl halide cyanation and Hiyama cross-coupling reactions. Also, less toxic potassium hexacyanoferrate(II) trihydrate was used as cyanide source in aryl halide cyanation and Hiyama cross-coupling was performed under fluoride free condition. Both reactions proceeded well with Pd NPs under ligand free circumstances to give good to excellent yields. The Pd NPs were recovered after each reaction and

  摘要在目前的工作中，使用黑胡椒（Piper nigrum）的水乙醇提取物从醋酸钯生物源制备钯纳米颗粒（Pd NPs），并通过各种分析技术，如 XRD、FE-SEM、EDS、TEM、ATR-IR 进行表征。 、UV-Vis 光谱、BET、TGA 和 ICP-OES 分析。将 Pd(II) 还原为 Pd(0) 是通过黑胡椒提取物中存在的各种植物化学物质的作用实现的，例如酚类、酸类、胡椒碱、胡椒基氰基乙酸乙酯、胡椒碱和 N-异丁基-十四烷-2,4-二烯酰胺. 生物合成的 Pd NPs 在芳基卤氰化和 Hiyama 交叉偶联反应中显示出优异的催化活性。此外，毒性较小的六氰基高铁酸钾 (II) 三水合物用作芳基卤氰化中的氰化物源，并且在无氟条件下进行 Hiyama 交叉偶联。在无配体的情况下，Pd NPs 的两个反应都进行得很好，以提供良好的收率。每次反应后 Pd NPs 被回收，并在芳基卤化氰化中循环最多
• Chagas Disease Drug Discovery: Multiparametric Lead Optimization against <i>Trypanosoma cruzi</i> in Acylaminobenzothiazole Series
  作者：Charlotte Fleau、Angel Padilla、Juan Miguel-Siles、Maria T. Quesada-Campos、Isabel Saiz-Nicolas、Ignacio Cotillo、Juan Cantizani Perez、Rick L. Tarleton、Maria Marco、Gilles Courtemanche

  DOI：10.1021/acs.jmedchem.9b01429

  日期：2019.11.27

  responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure–activity relationship, allowing optimization of antiparasite activity, physicochemical

  酰基氨基苯并噻唑命中被确定为克氏锥虫复制的潜在抑制剂，锥虫是负责恰加斯病的寄生虫。我们选择化合物1进行铅优化，旨在同时提高其抗克鲁氏锥虫活性（IC 50 = 0.63μM）和其人类代谢稳定性（人类清除率= 9.57 mL / min / g）。总共合成了39种1的类似物，并在体外进行了测试。我们建立了多参数结构与活性的关系，从而可以优化抗寄生虫活性，理化参数和ADME特性。我们将化合物50鉴定为具有改进的体外抗T. cruzi活性的高级铅（IC50 = 0.079μM）和增强的代谢稳定性（人类清除率= 0.41 mL / min / g）和口服途径。在耐受性评估后，有50种药物显示出有希望的体内功效。
• p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles
  作者：Larisa Politanskaya、Evgeny Tretyakov

  DOI：10.1055/s-0036-1591504

  日期：2018.2

  conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity. A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent

  摘要 报道了一种简单有效的合成氟化氨基取代的苯乙酮的方法，收率很好。所提出方法的核心是在存在对乙磺酸（p -TSA）经过乙炔基苯胺形成阶段的情况下，将Me 3 Si–C≡C–部分转化为MeC（= O）–基团。该反应是无金属的，在温和的条件下进行，并使用容易获得的起始化合物（三甲基甲硅烷基芳基乙炔衍生物）。该反应提供了获得氨基取代的苯乙酮的途径，其可以用作合成多氟氮杂杂环的前体，具有潜在的抗癌活性。 报道了一种简单有效的合成氟化氨基取代的苯乙酮的方法，收率很好。所提出方法的核心是在存在对乙磺酸（p -TSA）经过乙炔基苯胺形成阶段的情况下，将Me 3 Si–C≡C–部分转化为MeC（= O）–基团。该反应是无金属的，在温和的条件下进行，并使用容易获得的起始化合物（三甲基甲硅烷基芳基乙炔衍生物）。该反应提供了获得氨基取代的苯乙酮的途径，其可以用作合成多氟氮杂杂环的前体，具有潜在的抗癌活性。
• Photoresponsive Halogen-Bonded Liquid Crystals: The Role of Aromatic Fluorine Substitution
  作者：Marco Saccone、Matthias Spengler、Michael Pfletscher、Kim Kuntze、Matti Virkki、Christoph Wölper、Robert Gehrke、Georg Jansen、Pierangelo Metrangolo、Arri Priimagi、Michael Giese

  DOI：10.1021/acs.chemmater.8b04197

  日期：2019.1.22

  A new strategy for controlling the liquid crystalline and photophysical properties of supramolecular mesogens assembled via halogen bonding is reported. Changing the degree of fluorination at the halogen-bond donor of the supramolecular liquid crystal allows for the fine-tuning of the halogen bond strength and thereby provides control over the temperature range of the mesophase. At least three fluorine

  报道了控制通过卤素键组装的超分子介晶的液晶和光物理性质的新策略。改变超分子液晶的卤素键供体处的氟化度允许微调卤素键强度，从而提供对中间相的温度范围的控制。必须存在至少三个氟原子以确保卤素键供体的有效极化和中间相的形成。另外，发现在促进稳定的液晶相方面，stilbazole受体优于其偶氮吡啶吡啶对应物。
• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20170064962A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的杀虫性的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫组合物，以及使用这种杀虫组合物对这些害虫进行处理的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。