4-碘苯乙酸 | 1798-06-7

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酸
• 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: 4-碘苯乙酸
• 中文别名: 增产灵1号；对碘苯乙酸；4-碘苯基乙酸
• 英文名称: (4-iodophenyl)acetic acid
• 英文别名: 2-(4-iodophenyl)acetic acid；p-iodophenylacetic acid；4-Iodophenylacetic acid
• CAS: 1798-06-7
• 化学式: C₈H₇IO₂
• mdl: MFCD00082985
• 分子量: 262.047
• InChiKey: FJSHTWVDFAUNCO-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136°C
• 沸点：
  323.7±17.0 °C(Predicted)
• 密度：
  1.885±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  对光敏感，可与氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, LIGHT SENSITIVE
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  紧密封存于阴凉、干燥且避光的环境中，并远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Iodophenylacetic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
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.
4-Iodophenylacetic acid
Ingredient name:
CAS number: 1798-06-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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: C8H7IO2
Molecular weight: 262.0

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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, 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

4-碘苯乙酸是一种在合成其他化合物时用作类似物的化合物。研究表明，该化合物能有效对抗实体瘤，如前列腺癌和膀胱癌。此外，它还能通过与磷脂酰乙醇胺和磷脂酰胆碱脂质形成氢键来与膜表面相互作用。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  对碘苯乙酸甲酯	methyl 4-iodophenylacetate	63349-52-0	C9H9IO2	276.074
  苯乙酸	phenylacetic acid	103-82-2	C8H8O2	136.15
  对氨基苯乙酸	4-aminophenylacetic acid	1197-55-3	C8H9NO2	151.165
  4-碘苯基乙腈,	4-iodophenylacetonitrile	51628-12-7	C8H6IN	243.047

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  对碘苯乙酸甲酯	methyl 4-iodophenylacetate	63349-52-0	C9H9IO2	276.074
  4-碘苯乙醇	4-iodophenethyl alcohol	52914-23-5	C8H9IO	248.063
  4-碘苯乙酸乙酯	ethyl (4-iodophenyl)acetate	15250-46-1	C10H11IO2	290.101
  1-(4-碘苯基)丙烷-2-酮	1-(4-iodophenyl)-2-propanone	21906-36-5	C9H9IO	260.074
  2-(4-碘苯基)乙酰胺	4-iodophenylacetamide	84863-81-0	C8H8INO	261.062
  ——	2-(4-iodo-phenyl)-propionic acid methyl ester	41073-25-0	C10H11IO2	290.101
  2-(4-碘苯基)乙胺	4-iodophenethylamine	73918-57-7	C8H10IN	247.079
  对羟基苯乙酸	4-hydroxyphenylacetate	156-38-7	C8H8O3	152.15
  ——	2-(4-undecylphenyl)acetic acid	——	C19H30O2	290.446
  对氨基乙酸苯甲酯	methyl p-aminophenylacetate	39552-81-3	C9H11NO2	165.192

反应信息

• 作为反应物：
  描述：

  4-碘苯乙酸 在 copper(I) oxide 、 1-D-O-Methyl-chiro-inositol 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以84%的产率得到对羟基苯乙酸
  参考文献：
  名称：

  铜和1-（-）-邻苯二酚在空气中催化芳基卤化物的羟基化和胺化

  摘要：

  1 -（-）-木瓜醇，一种从橡胶工业废水中获得的天然产物，被用作铜催化的羟基卤化和芳基卤化物胺化的有效配体，以选择性地在水中或95％的乙醇中生成酚和芳基胺。另外，在空气中以100g的规模验证了2-氯-4-羟基苯甲酸的羟基化。

  DOI：

  10.1016/j.tetlet.2020.152222
• 作为产物：
  描述：

  苯乙酸 在 碘 、 硝酸 、 溶剂黄146 作用下， 生成 4-碘苯乙酸
  参考文献：
  名称：

  Datta; Chatterjee, Journal of the American Chemical Society, 1919, vol. 41, p. 295

  摘要：

  DOI：

文献信息

• Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
  作者：Amanda F. Silva、Marco A. S. Afonso、Rodrigo A. Cormanich、Igor D. Jurberg

  DOI：10.1002/chem.201905812

  日期：2020.5.4

  visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates

  据报道可见光促进的光化学方案用于芳基重氮乙酸酯与硼酸的偶联。与没有光照的相同方案相比，这种光化学反应显示出极大的增强。除少数情况外，在黑暗（热过程）中的室温耦合通常不起作用。如果这样做的话，很可能还涉及到游离卡宾作为关键中间体。可替代地，光化学反应显示出广泛的范围，可以在空气中进行并且耐受各种各样的官能团。反应进化监测，DFT计算和控制实验已用于评估这种复杂机制的主要方面。具有生物活性的分子阿迪芬，苯那西嗪和阿普生已经被制备为合成应用的实例。
• Piperazine and homopiperazine compounds
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20030153556A1

  公开（公告）日：2003-08-14

  Compounds are provided having a piperazine or homopiperazine ring which are useful in the treatment of thrombosis.

  提供了具有哌嗪或同源哌嗪环的化合物，这些化合物在治疗血栓症方面很有用。
• Azabicycloalkane compounds
  申请人：——

  公开号：US20040242622A1

  公开（公告）日：2004-12-02

  This invention provides compounds of formula I: 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The compounds of this invention possess both &bgr; 2 adrenergic receptor agonist and muscarinic receptor antagonist activity. Such compounds are useful for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

  这项发明提供了式I的化合物： 其中R1、R2、R3、R4、R5、R6和R7如规范中所定义，或其药用可接受盐、溶剂或立体异构体。本发明的化合物具有β2肾上腺素受体激动剂和肌碱受体拮抗剂活性。这些化合物对治疗肺部疾病，如慢性阻塞性肺病和哮喘，是有用的。
• Zirconium catalyzed amide formation without water scavenging
  作者：Helena Lundberg、Fredrik Tinnis、Hans Adolfsson

  DOI：10.1002/aoc.5062

  日期：2019.9

  A scalable homogeneous metal‐catalyzed protocol for direct amidation of carboxylic acids is presented. The use of 2–10 mol% of the commercially available Zr(Cp)2(OTf)2·THF results in high yields of amides at moderate temperature, using an operationally convenient reaction protocol that circumvents the use of water scavenging techniques.

  提出了一种可扩展的均质金属催化方案，用于羧酸的直接酰胺化。使用2-10 mol％的市售Zr（Cp）2（OTf）2 ·THF可以在中等温度下获得高产率的酰胺，这是通过操作方便的反应规程来规避水清除技术的使用。
• Para-aryl or heterocyclic substituted phenyl glucokinase activators
  申请人：——

  公开号：US20020002190A1

  公开（公告）日：2002-01-03

  Para-aryl or heteroaryl substituted phenyl amides which are active as glucokinase activators to increase insulin secretion which makes them useful for treating type II diabetes.

  对于糖激酶激活剂活性的对-芳基或杂芳基取代的苯酰胺，可以增加胰岛素分泌，因此对治疗II型糖尿病有用。

表征谱图