2-羧基苯乙烯 | 612-40-8

• 物质功能分类: 香精与香料 - 合成香料 - 芳香肉桂酸、酯及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-羧基苯乙烯
• 中文别名: 2-羧基肉桂酸
• 英文名称: 2-carboxycinnamic acid
• 英文别名: o-Carboxyzimtsaeure；o-carboxycinnamic acid；2-Carboxy-zimtsaeure；2-(2-Carboxyethenyl)benzoic acid
• CAS: 612-40-8
• 化学式: C₁₀H₈O₄
• mdl: MFCD00004380
• 分子量: 192.171
• InChiKey: SCWPNMHQRGNQHH-UHFFFAOYSA-N

物化性质

• 熔点：
  197-202 °C
• 沸点：
  248.14°C (rough estimate)
• 密度：
  1.396±0.06 g/cm3 (20 ºC 760 Torr)
• 稳定性/保质期：

  性质与稳定性：在常温常压下，该物质不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2917399090
• 储存条件：
  贮存： 将密器密封后，储存在密封的主要容器中，并放置于阴凉、干燥的地方。

SDS

Name:	2-Carboxycinnamic Acid 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	612-40-8

Section 1 - Chemical Product MSDS Name:2-Carboxycinnamic Acid 98% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
612-40-8	2-Carboxycinnamic Acid	98%	210-308-9

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

---

Section 4 - FIRST AID MEASURES
Eyes: 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 612-40-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 206 - 208 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: slightly soluble in water
Specific Gravity/Density:
Molecular Formula: C10H8O4
Molecular Weight: 192.0536

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 612-40-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Carboxycinnamic Acid - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 612-40-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 612-40-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 612-40-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-羧基苯乙烯 在 alkaline KMNO₄ 作用下， 生成 邻羧基苯甲醛
  参考文献：
  名称：

  Ehrlich, Monatshefte fur Chemie, 1889, vol. 10, p. 575

  摘要：

  DOI：
• 作为产物：
  描述：

  苏丹-1 在 双氧水 、 溶剂黄146 作用下， 生成 2-羧基苯乙烯
  参考文献：
  名称：

  Bigiavi; Cerchiai, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1922, vol. <5> 31 II, p. 28

  摘要：

  DOI：

文献信息

• A PdCl2-ionic liquid brush assembly: an efficient and reusable catalyst for Mizoroki-Heck reaction in neat water
  作者：Xianying Shi、Xiaoyan Han、Wenjuan Ma、Juan Fan、Junfa Wei

  DOI：10.1002/aoc.1857

  日期：2012.1

  An efficient and reusable heterogeneous catalytic assembly of PdCl2 held in ionic liquid brushes has been synthesized and an environmentally‐friendly procedure was developed for coupling aryl iodides with acrylic acid. These reactions were conducted in water under aerobic conditions with water‐insoluble or even solid aryl iodides and they proceeded smoothly and cleanly without any organic co‐solvent

  合成了一种高效且可重复使用的离子液体刷中容纳的PdCl 2异质催化组件，并开发了一种环境友好的程序，用于将芳基碘化物与丙烯酸偶联。这些反应是在有氧条件下与水不溶性或什至固体芳基碘化物在水中进行的，反应平稳，清洁，无需任何有机助溶剂或其他添加剂。发现0.5摩尔％（基于Pd原子）剂量的催化剂足以进行Mizoroki-Heck反应。反应后，可通过简单过滤将催化剂轻松回收，并重复使用至少八次，而活性不会明显下降。该方案的优点是具有优异的产率，环境友好性和催化剂可回收性。版权所有©2011 John Wiley＆Sons，Ltd.
• Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters
  作者：Xiao-Yu Lu、Ang Gao、Qi-Le Liu、Ze-Jie Xia

  DOI：10.1016/j.tet.2021.132259

  日期：2021.7

  The first photoinduced copper-catalyzed dual decarboxylative cross-coupling of α,β-unsaturated carboxylic acids and redox-active esters has been developed. This reaction enabled C(sp2)–C(sp3) bond formation, which afforded a variety of synthetically valuable alkene derivatives. Many α,β-unsaturated carboxylic acids and redox-active ester derivatives were tolerant to this reaction. The reaction also

  已经开发出第一个光诱导铜催化的 α,β-不饱和羧酸和氧化还原活性酯的双脱羧交叉偶联。该反应使 C( sp 2 )–C( sp 3 ) 键形成成为可能，从而提供了多种具有合成价值的烯烃衍生物。许多 α,β-不饱和羧酸和具有氧化还原活性的酯衍生物都耐受该反应。该反应还耐受许多常见的官能团。
• Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
  作者：Xiao-Yu Lu、Ze-Jie Xia、Ang Gao、Qi-Le Liu、Run-Chuang Jiang、Chuang-Chuang Liu

  DOI：10.1021/acs.joc.1c00726

  日期：2021.7.2

  Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)–C(sp3) bond constructed by the

  在此，开发了一种镍/钌双策略用于 α,β-不饱和羧酸和环酮肟酯之间的光诱导脱羧交叉偶联。反应机理不同于先前的光诱导α,β-不饱和羧酸脱羧。该反应可能通过环丙烷镍中间体进行。通过上述反应构建的 C(sp 2 )–C(sp 3 ) 键为在温和的反应条件下获得各种氰基烷基烯烃提供了一种有效的方法，它们是有机和药物化学中具有合成价值的有机骨架。该协议容忍许多关键功能组，并为复杂有机分子的修饰提供了途径。
• Aminohydroxylation of Olefins
  申请人：The Scripps Research Institute

  公开号：US06350905B1

  公开（公告）日：2002-02-26

  Osmium-catalyzed aminohydroxylation reactions are accelerated and expanded in scope by the use of olefinic substrates having ionic groups, either anionic or cationic. The use of ionic groups on olefinic substrates also extends the aminohydroxylatable positions of unsaturations to include &agr;,&bgr;, &bgr;,&ggr;, and &ggr;,&dgr; positions, with respect to such ionic groups. A mechanism for the disclosed acceleration and extension is provided.

  铂催化的氨羟基化反应通过使用具有离子基团的烯烃底物（无论是阴离子还是阳离子）而得到加速和扩展。在烯烃底物上使用离子基团还将氨羟基化位置扩展到与这些离子基团相关的α，β，β，γ和γ，δ位置。提供了所述加速和扩展的机制。
• Synthesis, biological evaluation and molecular docking studies of indeno [1, 2-c] pyrazol derivatives as inhibitors of mitochondrial malate dehydrogenase 2 (MDH2)
  作者：Farzaneh Ahmadi、Matthias Engel、Mehdi M. Baradarani

  DOI：10.1016/j.bioorg.2021.104779

  日期：2021.5

  Hypoxia inducible factor-1 (HIF-1) is a pivotal transcription factor, which is strongly correlated with the induction of angiogenesis, tumor survival, metastasis, and cell proliferation, making it a pivotal therapeutic target for solid tumor therapeutic agents. Herein, a new series of multi-functional chemical probes were designed including principal groups, viz. adamantyl and indene, at various locations

  缺氧诱导因子-1 (HIF-1) 是一种关键的转录因子，与血管生成、肿瘤存活、转移和细胞增殖的诱导密切相关，使其成为实体瘤治疗药物的关键治疗靶点。在此，设计了一系列新的多功能化学探针，包括主基团，即。金刚烷基和茚，位于母体化合物 LW6 的不同位置。对设计的化合物及其与 HIF-1α 和苹果酸脱氢酶 2 (MDH2) 的关系进行了分子对接研究。我们的化合物对 MDH2 的抑制预计会降低 NADH 水平。事实上，对乳腺癌细胞系 4T1 的治疗导致 NADH 浓度的强烈降低。(E)-3-(4-((3r, 5r,50  = 59 nM），并且在缺氧条件下具有最佳抑制潜力（MCF-7：IC 50  = 57 nM）。该化合物还给出了最高的对接之一“高于在初始对接运行中使用 LW6 获得的分数（-31.63 kcal/mol）（PDB 代码：4WLO）。从对接结果中还合成了其他收率良好的相关化合物，