3-(2-chloro-4-fluorophenyl)-2-propenoic acid | 133220-86-7

• 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
• 英文名称: 3-(2-chloro-4-fluorophenyl)-2-propenoic acid
• 英文别名: 3-(2-Chloro-4-fluorophenyl)acrylic acid；3-(2-chloro-4-fluorophenyl)prop-2-enoic acid
• CAS: 133220-86-7
• 化学式: C₉H₆ClFO₂
• 分子量: 200.597
• InChiKey: RJCWBTRMWGOREZ-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C
• 密度：
  1.3522 (estimate)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知危险反应。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 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：
  H302,H315,H319,H335

SDS

Name:	2-Chloro-4-Fluorocinnamic Acid Material Safety Data Sheet
Synonym:	3-(2-Chloro-4-Fluorophenyl)Propenoic Aci
CAS:	133220-86-7

Section 1 - Chemical Product MSDS Name:2-Chloro-4-Fluorocinnamic Acid Material Safety Data Sheet
Synonym:3-(2-Chloro-4-Fluorophenyl)Propenoic Aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
133220-86-7	2-Chloro-4-Fluorocinnamic Acid	ca 100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
Causes 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.
Chronic:
No information found.

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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. 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.

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

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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. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash clothing before reuse.
Storage:
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.

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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# 133220-86-7: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: green
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 245-247 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: C9H6ClFO2
Molecular Weight: 200.4922

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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, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Chlorine, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, fluorine.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 133220-86-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-4-Fluorocinnamic Acid - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 133220-86-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 133220-86-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 133220-86-7 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：

  3-(2-chloro-4-fluorophenyl)-2-propenoic acid 在 recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase 、 氨基甲酸铵 作用下， 以 水 为溶剂， 反应 48.0h， 以99%的产率得到
  参考文献：
  名称：

  使用氨基甲酸铵作为氨源，增强丙烯酸对映体纯的卤代苯丙氨酸的生物催化生产†

  摘要：

  利用蓝细菌苯丙氨酸氨裂合酶（PAL）和氨基甲酸铵反应缓冲液的新型组合，已开发出一种与工业相关的强化方法，用于生产对映纯的卤代苯丙氨酸。该工艺的STYs大于200 g L -1 d -1，ee≥98 ％，简化了催化剂/反应缓冲液的制备和后处理。

  DOI：

  10.1039/c6cy00855k
• 作为产物：
  描述：

  2-chloro-5-nitrocinnamic acid 以75%的产率得到3-(2-chloro-4-fluorophenyl)-2-propenoic acid
  参考文献：
  名称：

  Herbicidal cinnamic ester uracils

  摘要：

  具有结构##STR1##的化合物，其中：R为C.sub.1 -C.sub.12烷基，直链或支链；或C.sub.3 -C.sub.12烯基；R.sup.1为C.sub.1 -C.sub.12烷基，直链或支链，且可形成碳环；X为氢或卤素；Y为氢或卤素；所述化合物具有除草活性。还公开了包括该化合物和载体的除草剂组合物，以及利用该化合物控制有害植物生长的方法。还公开了制备这类化合物的方法。

  公开号：

  US04979982A1

文献信息

• Enantioselective Copper‐Catalysed Allylic Alkylation of Cinnamyl Chlorides by Grignard Reagents using Chiral Phosphine‐Phosphite Ligands
  作者：Wibke Lölsberg、Shute Ye、Hans‐Günther Schmalz

  DOI：10.1002/adsc.201000213

  日期：2010.10.9

  copper(I)-catalysed SN2′-type allylic substitution of E-3-aryl-allyl chlorides (cinnamyl chlorides) using Grignard reagents represents a powerful method for the synthesis of compounds carrying a benzylic stereocentre. By screening a small library of modular chiral phosphine-phosphite ligands a new copper(I)-based catalyst system was identified which allows the performance of such reactions with exceptional high

  使用格氏试剂的铜（I）催化的E -3-芳基-烯丙基氯化物（肉桂酰氯）的S N 2'型烯丙基取代代表了一种合成具有苄基立体中心的化合物的有效方法。通过筛选小的模块化手性膦-亚磷酸酯配体文库，确定了一种新的基于铜（I）的催化剂体系，该体系可以以极高的区域和对映体选择性进行此类反应。使用TADDOL衍生的配体（3 mol％），溴化铜（I）·二甲基硫醚（CuBr·SMe 2）（2.5 mol％）和甲基叔丁基醚（MTBE）获得最佳结果。制备了具有高达99％ee的各种（1-烷基-烯丙基）苯衍生物（GC）的分离产率高达99％。在大多数情况下，产物包含少于3％的线性区域异构体（除了邻位取代的底物）。富电子和电子不足的肉桂酰氯均已成功使用。通过比较实验和计算出的CD光谱来确定产品的绝对构型。通过与亚硫酰氯反应，由相应的醇制备底物。通过在MTBE中在三苯基膦（PPh 3）（3mol％）的存在下在低温下用CuBr·SMe
• AMINOPYRAZOLE DERIVATIVES
  申请人：Bur Daniel

  公开号：US20110034516A1

  公开（公告）日：2011-02-10

  The invention relates to aminopyrazole derivatives of formula (I), wherein A, E, R 1 and R 2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

  这项发明涉及公式（I）的氨基吡唑衍生物， 其中A、E、R1和R2如描述中所定义，它们的制备以及它们作为药用活性化合物的用途。
• Electrochemical Intermolecular Monofluoroalkylation of α,β-Unsaturated Carboxylic Acids and Heteroaromatics with 2-Fluoromalonate Esters
  作者：Zhong-Wei Hou、Ting Jiang、Ting-Xia Wu、Lei Wang

  DOI：10.1021/acs.orglett.1c03284

  日期：2021.11.5

  An electrochemical approach for the preparation of monofluorides from α,β-unsaturated carboxylic acids and heteroaromatics with readily available 2-fluoromalonate esters as monofluoroalkyl radical precursors has been developed. The electrosynthesis employs ferrocene (Cp2Fe) as a catalyst in a simple undivided cell with a broad substrate scope, which obviates the need for sacrificial oxidizing reagents

  已经开发了一种用于从 α,β-不饱和羧酸和杂芳烃制备单氟化物的电化学方法，使用容易获得的 2-氟丙二酸酯作为单氟烷基自由基前体。电合成采用二茂铁 (Cp 2 Fe) 作为催化剂，在一个简单的未分割电池中，底物范围广泛，无需牺牲氧化剂。
• Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors
  作者：Yuanbiao Tu、Yiqiang OuYang、Shan Xu、Yan Zhu、Gen Li、Chao Sun、Pengwu Zheng、Wufu Zhu

  DOI：10.1016/j.bmc.2016.02.017

  日期：2016.4

  cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines

  设计，合成并评估了两个带有肉桂酰胺部分的afatinib衍生物系列（10a – n和11a – h），并评估了其对四种癌细胞系（A549，PC-3，MCF-7和Hela）的IC 50值。进一步评估了两种选择的化合物（10e，10k）对EGFR和VEGFR2 / KDR激酶的抑制活性。其中七个化合物表现出出色的细胞毒性活性和选择性，IC 50值在个位数μM到纳摩尔范围内。它们中的三个等于比阳性对照afatinib对一种或多种细胞系更有活性。最有前途的化合物10k表现出对A549，PC-3，MCF-7和Hela癌细胞系和EGFR激酶的最佳活性，IC 50值分别为0.07±0.02μM，7.67±0.97μM，4.65±0.90μM和4.83±1.28μM。分别比阿法替尼（0.05±0.01μM，4.1±2.47μM，5.83±1.89μM和6.81±1.77μM）活性更高。化合物10e（IC 50
• [EN] ARYL SUBSTITUTED CARBOXAMIDE DERIVATIVES AS CALCIUM OR SODIUM CHANNEL BLOCKERS<br/>[FR] DÉRIVÉS DE CARBOXAMIDE SUBSTITUÉS PAR ARYLE COMME INHIBITEURS DES CANAUX CALCIQUES OU SODIQUES
  申请人：RAQUALIA PHARMA INC

  公开号：WO2010137351A1

  公开（公告）日：2010-12-02

  The present invention relates to aryl substituted carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof, which have blocking activities of T-type calcium channels or voltage gated sodium channels as the tetrodotoxin-sensitive (TTX-S)blockers such as NaV1.3 and NaV1.7, and which are useful in the treatment or prevention of disorders and diseases in which T-type calcium channels or voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which T-type calcium channels or voltage gated sodium channels are involved.

  本发明涉及式(I)或其药物可接受的盐的芳基取代羧酰胺衍生物，其具有T型钙通道或电压门控钠通道的阻断活性，如NaV1.3和NaV1.7等Tetrodotoxin敏感（TTX-S）阻断剂，适用于治疗或预防涉及T型钙通道或电压门控钠通道的疾病和紊乱。本发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及T型钙通道或电压门控钠通道的疾病中使用这些化合物和组合物的用途。