2-((4-碘苯基)氨基)乙酸乙酯 | 14108-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-((4-碘苯基)氨基)乙酸乙酯
• 英文名称: ethyl (4-iodophenyl)glycinate
• 英文别名: Ethyl 2-(4-iodoanilino)acetate
• CAS: 14108-76-0
• 化学式: C₁₀H₁₂INO₂
• mdl: MFCD00176764
• 分子量: 305.115
• InChiKey: VEMDCCDETKYAEB-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86
• 沸点：
  339.8±22.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2922499990

SDS

Name:	Ethyl 2-(4-iodoanilino)acetate 97% Material Safety Data Sheet
Synonym:
CAS:	14108-76-0

Section 1 - Chemical Product MSDS Name:Ethyl 2-(4-iodoanilino)acetate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14108-76-0	Ethyl 2-(4-iodoanilino)acetate	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. Immediately 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. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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# 14108-76-0: 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: grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84 - 86 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: C10H12INO2
Molecular Weight: 305

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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, acids, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen iodide, iodine, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14108-76-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-(4-iodoanilino)acetate - 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# 14108-76-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14108-76-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14108-76-0 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：

  2-((4-碘苯基)氨基)乙酸乙酯 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium carbonate 、 二乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 N-((4-ethynyl)phenyl)glycine ethyl ester
  参考文献：
  名称：

  合成和二茂铁联双-富勒烯的表征[60]哑铃†

  摘要：

  制备了一个新的[60]富勒烯哑铃，它由两个通过酰胺键连接到中心二茂铁单元的富勒吡咯烷组成，并通过元素分析，1 H NMR，UV / Vis，荧光和质谱进行了全面表征。通过循环伏安法测定的电化学性质显示出二茂铁和富勒烯单元之间的基态电子连通。另外，提出了用于另一种连接方法的二茂铁构件的制备。

  DOI：

  10.1039/c2dt12097f
• 作为产物：
  描述：

  重氮乙酸乙酯 、 对碘苯胺 在 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 硝基甲烷 为溶剂， 以67%的产率得到2-((4-碘苯基)氨基)乙酸乙酯
  参考文献：
  名称：

  稳定的自由基阳离子盐引发N–H插入和相关的质子转移延迟三组分反应

  摘要：

  N–H插入反应仅形成单个加成产物，不需要缓慢添加重氮组分。更重要的是，在催化量的三芳基ami盐存在下，我们提出了苯胺与重氮乙酸盐和偶氮二羧酸盐的反应，从而以高收率得到了相应的复杂的不对称缩醛。这是稳定的阳离子阳离子盐促进质子转移-延迟三组分反应的第一个例子。

  DOI：

  10.1016/j.tetlet.2016.04.012

文献信息

• Stable radical cation salt initiated N–H insertion and related proton-transfer-delay three-component reaction
  作者：Congde Huo、Haisheng Xie、Caixia Yang、Jie Dong、Yajun Wang

  DOI：10.1016/j.tetlet.2016.04.012

  日期：2016.5

  present the reaction of anilines with both diazoacetates and azodicarboxylates in the presence of catalytic amounts of triarylaminium salt giving the corresponding complex unsymmetrical aminals in high yields. This is the first example of stable radical cation salt promoted proton-transfer-delay three-component reaction.

  N–H插入反应仅形成单个加成产物，不需要缓慢添加重氮组分。更重要的是，在催化量的三芳基ami盐存在下，我们提出了苯胺与重氮乙酸盐和偶氮二羧酸盐的反应，从而以高收率得到了相应的复杂的不对称缩醛。这是稳定的阳离子阳离子盐促进质子转移-延迟三组分反应的第一个例子。
• Unnatural α-Amino Acid Synthesized through α-Alkylation of Glycine Derivatives by Diacyl Peroxides
  作者：Hao Tian、Wentao Xu、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.0c01574

  日期：2020.7.2

  We have developed a protocol for catalyst- and additive-free α-alkylation reactions of glycine derivatives with diacyl peroxides, which proceed by a pathway involving addition of alkyl radicals to imine intermediates. The diacyl peroxide substrate acts as both alkylation agent and oxidizing agent, which means it is atom-economical. It was applied to various glycine derivatives, dipeptides, and a 3

  我们已经开发出用于甘氨酸衍生物与二酰基过氧化物的无催化剂和无添加剂的α-烷基化反应的方案，该方案通过涉及将烷基自由基加成至亚胺中间体的途径进行。过氧化二酰基的底物既充当烷基化剂又充当氧化剂，这意味着它是原子经济的。它已应用于各种甘氨酸衍生物，二肽和3,4-二氢喹喔啉-2（1 H）-one衍生物，并且可以克量进行，表明其可用于后期功能化。
• 一种可见光催化二级胺进行α-位烷基化的合成 方法
  申请人：中国科学院理化技术研究所

  公开号：CN104230734B

  公开（公告）日：2016-06-29

  本发明公开了一种可见光催化二级胺进行α-位烷基化的合成方法，包括以下步骤：1)将无机金属盐和N-芳基甘氨酸酯加入到有机溶剂中，得溶液A；2)将β-酮酸酯加入溶液A中，得溶液B；3)在空气氛围中，用可见光照射溶液B，得到N-芳基甘氨酸酯的烷基化产物。本发明采用廉价无机金属盐和二级胺原位配位生成的化合物既作光敏剂，又作催化剂实现二级胺的α-位烷基化反应。本发明体系利用LED蓝光或者绿光作为可见光光源，不需要加入额外的光敏剂，不需要加入额外的电子受体，以空气中的氧气作为终端氧化剂，整个合成反应条件温和、操作简单、原子经济。
• Visible‐Light‐Induced Oxidative α‐Alkylation of Glycine Derivatives with Ethers under Metal‐Free Conditions
  作者：Yang Song、Hao Zhang、Jiabao Guo、Yifei Shao、Yuzhou Ding、Li Zhu、Xiaoquan Yao

  DOI：10.1002/ejoc.202101242

  日期：2021.11.25

  A novel visible-light-induced coupling reaction of glycine derivatives with ethers is reported. Its scope was expanded to α-amino esters,α-amino ketones and α-amino amides. Not only various α-amino esters but also cyclic and acyclic ethers were well tolerated in this strategy. Metal-free catalysis and efficient synthesis under mild conditions are notable features of this method.

  报道了甘氨酸衍生物与醚的新型可见光诱导偶联反应。其范围扩大到α-氨基酯、α-氨基酮和α-氨基酰胺。在该策略中，不仅各种 α-氨基酯而且环状和无环醚都具有良好的耐受性。该方法的显着特点是无金属催化和温和条件下的高效合成。
• Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
  作者：Jialin Xie、Yuanqiong Huang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.7b02767

  日期：2017.11.17

  An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization cascade process, starts from readily available and inexpensive materials, uses molecular oxygen as a co-oxidant, and has a broad substrate scope.

  报道了通过甘氨酸衍生物和5-烷氧基恶唑之间的反应获得四取代的4，5-双羰基咪唑的原子经济方法。该方法涉及铜催化的好氧氧化[2 + 3]环化/芳香化反应级联过程，从容易获得且廉价的材料开始，使用分子氧作为助氧化剂，具有广泛的底物范围。