3-苯甲酰丙烯酸 | 583-06-2

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苯甲酰丙烯酸
• 中文别名: 苯甲醯丙烯酸；3-苯基酰基丙烯酸
• 英文名称: 3-benzoylacrylic acid
• 英文别名: β-benzoylacrylic acid；4-oxo-4-phenylbut-2-enoic acid；beta-Benzoylacrylic acid
• CAS: 583-06-2
• 化学式: C₁₀H₈O₃
• mdl: MFCD00014015
• 分子量: 176.172
• InChiKey: PLPDHGOODMBBGN-UHFFFAOYSA-N

物化性质

• 熔点：
  94-97 °C(lit.)
• 沸点：
  267.77°C (rough estimate)
• 密度：
  1.1958 (rough estimate)
• 稳定性/保质期：

  溶于醇、醚及热水，微溶于冷水。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 2811 6
• 海关编码：
  2918300090
• 储存条件：
  本品应密封保存。

SDS

Name:	3-Benzoylacrylic acid Material Safety Data Sheet
Synonym:	4-Oxo-4-phenyl-2-butenoic acid; 4-Phenyl-4-oxo-2-butenoic acid; Acrylic acid, 3-benzoyl- (6CI,7CI,8CI); Benzoylacrylic acid
CAS:	583-06-2

Section 1 - Chemical Product MSDS Name:3-Benzoylacrylic acid Material Safety Data Sheet
Synonym:4-Oxo-4-phenyl-2-butenoic acid; 4-Phenyl-4-oxo-2-butenoic acid; Acrylic acid, 3-benzoyl- (6CI,7CI,8CI); Benzoylacrylic acid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
583-06-2	3-Benzoylacrylic acid	ca.100	209-496-5

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.
Inhalation:
Causes respiratory tract irritation. 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.
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.
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 appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Keep refrigerated. (Store below 4C/39F.) Keep container closed when not in use. 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# 583-06-2: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 96.00 - 98.00 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: C10H8O3
Molecular Weight: 176.17

---

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, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 583-06-2: EM9259050 LD50/LC50:
CAS# 583-06-2: Oral, mouse: LD50 = 250 mg/kg.
Carcinogenicity:
3-Benzoylacrylic acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION
Other No information available.

---

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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 583-06-2: No information available.
Canada
CAS# 583-06-2 is listed on Canada's NDSL List.
CAS# 583-06-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 583-06-2 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：淡黄色片状结晶体。一水合物的熔点为-64℃，无水物的熔点为99℃。该物质能溶于醇、醚及热水，并且微溶于冷水。

用途：主要用于有机合成中间体和检验酚类化合物的试剂。

生产方法：通过苯与顺丁烯二酸酐反应得到。

反应信息

• 作为反应物：
  描述：

  3-苯甲酰丙烯酸 在 盐酸 作用下， 反应 72.0h， 以81%的产率得到α-chloro-β-benzoylpropionic acid
  参考文献：
  名称：

  β-苯甲酰丙酸部分溴化衍生物的内酯化研究

  摘要：

  此处描述了一些溴化衍生物在亚甲基链上的 ß-苯甲酰丙酸到相应的 2(5H)-呋喃酮或 2(3H)firanones，具体取决于取代和反应条件。丁烯内酯是不饱和的 γ-内酯，也可以被认为是 2(3H)呋喃酮 1 或 2(5H)-呋喃酮 2。2(5H)-呋喃酮环在自然界中广泛存在，但我们没有发现含有 2( 3H)-呋喃酮核。这可能是因为 2(5H)-呋喃酮更稳定，因此比相应的 2(3H)-异构体更丰富。几种天然产物以甾体内酯的糖苷形式存在于植物中，称为碳烯内酯。无论哪种形式，它们都会对人和动物的心肌发挥特定而强大的作用。四种新的丁烯内酯，（2（5H）形式），已经从抗生素链霉菌 TÜ 99 中分离出来，在初步测试中显示出对假单胞菌的抗生素活性。还从两个海洋链霉菌菌株 Β 5632 和 Β 3497 中分离出了四种新的 5-取代 α,β-不饱和内酯。已知 2 型手性 γ-取代丁烯内酯是有用的合成子

  DOI：

  10.1515/hc.2007.13.1.35
• 作为产物：
  描述：

  3-溴-4-氧代-4-苯基丁酸 在 sodium acetate 、 溶剂黄146 作用下， 生成 3-苯甲酰丙烯酸
  参考文献：
  名称：

  Bougault, Annales de Chimie (Cachan, France), 1908, vol. <8> 15, p. 501

  摘要：

  DOI：

文献信息

• Substituted benzoylacrylanilides
  申请人：Merck & Co., Inc.

  公开号：US04130661A1

  公开（公告）日：1978-12-19

  Novel substituted benzoylacrylanilides are prepared by reacting a substituted benzoylacrylic acid with a substituted aniline in the presence of a coupling agent. These acrylanilides have significant anticoccidial activity.

  通过在偶联剂的存在下将取代的苯甲酰丙烯酸与取代的苯胺反应，可以制备出新的取代苯甲酰丙烯腈。这些丙烯腈具有显著的抗球虫活性。
• Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride
  作者：Subrata Kumar Chaudhuri、Manabendra Saha、Amit Saha、Sanjay Bhar

  DOI：10.3762/bjoc.6.94

  日期：——

  4-Aryl-4-oxoesters undergo facile reduction of both the keto and the ester groups with methanolic NaBH₄ at room temperature to yield the corresponding 1-aryl-1,4-butanediols whereas 4-alkyl-4-oxoesters furnish the corresponding 1,4-butanolides via selective reduction of the keto moiety. Results of a detailed and systematic investigation of the reaction are described.

  4-芳基-4-氧代酯在室温下与甲醇中的NaBH₄发生反应，可以轻易地同时还原其酮基和酯基，生成相应的1-芳基-1,4-丁二醇，而4-烷基-4-氧代酯则通过选择性地还原酮基部分，得到相应的1,4-丁内酯。本文详细描述了这一反应的全面和系统性的研究结果。

• Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
  作者：Andrii Lozynskyi、Viktoria Zasidko、Dmytro Atamanyuk、Danylo Kaminskyy、Halyna Derkach、Olexandr Karpenko、Volodymyr Ogurtsov、Roman Kutsyk、Roman Lesyk

  DOI：10.1007/s11030-017-9737-8

  日期：2017.5

  AbstractHere it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(\(5R,6S,7R\))-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and \(\upbeta \)-aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder

  抽象的这里描述了新型rel-（\（5R，6S，7R \））-6-苯甲酰基-7-苯基-2-氧代-3,5,6,7-四氢-的合成，抗氧化剂和抗菌活性的测定2 H-硫代吡喃并[2，3 - d ]噻唑-5-羧酸。通过区域-和非对映选择性的杂-Diels-Alder反应，从5-芳叉基-4-硫代-2--2-噻唑烷酮和\（upbeta \）-芳酰基丙烯酸以高收率获得了目标化合物。通过NMR光谱证实了环加成的立体化学。进行抗氧化和抗菌活性筛选，鉴定出7种化合物（3c，3e，3f，3g，3k，3l，3p）具有高水平的自由基清除能力（43-77％DPPH测定），以及对金黄色葡萄球菌，枯草芽孢杆菌和白色念珠菌有显着影响的化合物（MIC 3.13-6.25 \（\ upmu \ hbox g / mL} \）），但对大肠杆菌有轻微影响。 图形概要
• 一种2，4-二取代嘧啶衍生物及其制备方法和用途
  申请人：成都赜灵生物医药科技有限公司

  公开号：CN112142731B

  公开（公告）日：2022-07-22

  本发明属于化学医药领域，具体涉及2，4‑二取代嘧啶衍生物及其制备方法和用途。本发明提供了一种2，4‑二取代嘧啶衍生物，其结构如式Ⅳ所示。本发明还提供了上述2，4‑二取代嘧啶衍生物的制备方法及其用途。本发明提供的2，4‑二取代嘧啶衍生物既可以作为具有JAK2和FLT3双功能靶点的激酶抑制剂，又可以是具有单独的JAK2或者FLT3功能靶点的激酶抑制剂，为制备多靶点抑制剂提供了新的选择。
• Thiazolidinone/thiazole based hybrids – New class of antitrypanosomal agents
  作者：Anna Kryshchyshyn、Danylo Kaminskyy、Oleksandr Karpenko、Andrzej Gzella、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.ejmech.2019.04.052

  日期：2019.7

  have been investigated as potent drugs for trypanosomiasis treatment, but no new drug has been marketed in the past 3 decades. 4-Thiazolidinone/thiazole as privileged structures and thiosemicarbazides cyclic analogs are well known scaffolds in novel antitrypanosomal agent design. We present here the design and synthesis of new hybrid molecules bearing thiazolidinone/thiazole cores linked by the hydrazone

  已经研究了各种化合物作为治疗锥虫病的有效药物，但是在过去的30年中，没有新的药物上市。4-噻唑烷酮/噻唑作为优先结构和硫代氨基脲环类似物是新型抗锥虫药物设计中众所周知的支架。我们在这里介绍新的杂合分子的设计和合成，这些杂合分子带有由zo基与各种分子片段连接的噻唑烷酮/噻唑核。结构优化导致具有苯基吲哚或苯基咪唑并[2,1- b ] [1,3,4]噻二唑部分的化合物对布鲁氏锥虫和冈比亚锥虫具有优异的抗锥虫活性。生物学研究允许鉴定出亚微摩尔水平的IC 50，良好的选择性指数，对人原代成纤维细胞的相对较低的细胞毒性以及较低的急性毒性的化合物。