2-氯-6-氟肉桂酸 | 392-22-3

• 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-氯-6-氟肉桂酸
• 中文别名: 2-氯-6-氟肉桂酸,PREDOMINANTLYTRANS
• 英文名称: 6-fluoro-2-chloro-trans-cinnamic acid
• 英文别名: 6-Fluor-2-chlor-trans-zimtsaeure；(E)-3-(2-chloro-6-fluoro-phenyl)-acrylic acid；2-Chloro-6-fluorocinnamic acid；(E)-3-(2-chloro-6-fluorophenyl)prop-2-enoic acid
• CAS: 392-22-3
• 化学式: C₉H₆ClFO₂
• mdl: MFCD00051582
• 分子量: 200.597
• InChiKey: NDWALECYVLNBQG-SNAWJCMRSA-N

物化性质

• 熔点：
  165-169 °C(lit.)
• 沸点：
  312.8±27.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 危险等级：
  IRRITANT
• 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：
  2916399090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Name:	2-Chloro-6-fluorocinnamic acid 98% Material Safety Data Sheet
Synonym:
CAS:	392-22-3

Section 1 - Chemical Product MSDS Name:2-Chloro-6-fluorocinnamic acid 98% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
392-22-3	2-Chloro-6-fluorocinnamic acid	98%	unlisted

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.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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.
Ingestion:
Get medical aid. 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.
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.
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.

---

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.

---

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# 392-22-3: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 163 - 165 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C9H6ClFO2
Molecular Weight: 200.6

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 392-22-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-6-fluorocinnamic 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# 392-22-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 392-22-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 392-22-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

2-氯-6-氟肉桂酸广泛用于精细化学品和合成香料等领域。

反应信息

• 作为反应物：
  描述：

  2-氯-6-氟肉桂酸 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.17h， 生成 (E)-1-[(E)-3-(2-chloro-6-fluorophenyl)acryloyl]-3-(3,4,5-trimethoxybenzylidene) piperidin-2-one
  参考文献：
  名称：

  设计和合成姜黄素的新型二羰基类似物（DACs）作为有效的抗炎药，可抵抗LPS诱导的急性肺损伤（ALI）

  摘要：

  制备了一系列新的姜黄素二羰基类似物（DACs），并评估了它们的抗炎特性。初步结果表明，本研究中测试的绝大多数化合物都可以有效抑制LPS诱导的肿瘤坏死因子（TNF）-α和白介素（IL）-6的产生。讨论了化合物的构效关系。化合物5a27和5a28显示出最有效的抗炎活性和具有比姜黄素更高的结构稳定性和生物利用度口服体外。从机制上讲，它们通过抑制有丝分裂原激活的蛋白激酶（MAPK）信号传导和NF-κB的核易位来抑制巨噬细胞的激活。在体内，5a275a28和5a28可以显着减轻脂多糖（LPS）诱导的急性肺损伤（ALI）。活性化合物使肺的干/湿比显着标准化，这与中性粒细胞浸润的抑制和促炎性细胞因子的产生是一致的。总的来说，这些结果提出了一系列新的姜黄素类似物，作为有望用于治疗ALI的抗炎药。

  DOI：

  10.1016/j.ejmech.2019.02.042
• 作为产物：
  描述：

  2-氯-6-氟甲苯 在 二硫化碳 、 二氯氧化铬 、 溶剂黄146 作用下， 生成 2-氯-6-氟肉桂酸
  参考文献：
  名称：

  Willstaedt, Chemische Berichte, 1931, vol. 64, p. 2688,2692

  摘要：

  DOI：

文献信息

• Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents
  作者：P. Asha Bhanu、B. China Raju、Y. Jayavardhana Rao、G. Narasimha、B. Kesava Rao

  DOI：10.1007/s00044-019-02476-5

  日期：2020.2

  first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity. Series of 7-hydroxyflavanone based novel isoxazoles 6a–h and acrylates 8a–k were synthesized. Isoxazole compounds 6e, 6g–h and acrylates

  本研究旨在合成新型的7-羟基黄酮类化合物，并评估其生物学活性。两个系列的化合物，例如2-苯基-7-（（3-苯基异恶唑-5-基）甲氧基）苯并二氢吡喃-4-酮（6a–h）和丙烯酸4-氧代-2-苯基苯并七基-7-基丙烯酸酯（8a– k）由7-羟基黄烷酮合成。所有化合物都经过了抗微生物活性和分子对接研究。结果表明，与标准药物相比，化合物6e，6g–h，8h–i和8k具有最强的抗菌活性。此外，对接研究表明化合物6a和8h分别具有最高的固醇14-α脱甲基酶和DNA促旋酶B结合亲和力分数。这是首次报告7-羟基黄酮酮衍生物的独特合成方法，并且其抗微生物活性已通过计算机研究证明。此外，本研究对于合成新型化合物及其生物学活性的建设性研究很有用。 合成了一系列基于7-羟基黄酮的新型异恶唑6a–h和丙烯酸酯8a–k。异恶唑化合物6e，6g-h和丙烯酸酯8h-i和8k被认为是最有效的抗微生物剂。
• Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases
  作者：Aamer Saeed、Parvez Ali Mahesar、Sumera Zaib、Muhammad Siraj Khan、Abdul Matin、Mohammad Shahid、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2014.03.015

  日期：2014.5

  The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel

  本研究报告了肉桂酰胺衍生物的合成及其作为胆碱酯酶和抗癌剂抑制剂的生物活性。对大脑乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的受控抑制可能会减缓阿尔茨海默氏病（AD）中的神经变性。确定了苯基肉桂酰胺衍生物对Eel乙酰胆碱酯酶（EeAChE）和马血清丁酰胆碱酯酶（hBChE）的抗胆碱酯酶活性，某些化合物似乎是EeAChE和hBChE的中等有效抑制剂。化合物3-（2-（苄氧基）苯基）-N-（3,4,5-三甲氧基苯基）丙烯酰胺（3i）具有IC 50的最大抗EeAChE活性0.29±0.21μM，而3-（2-氯-6-硝基苯基）-N-（3,4,5-三甲氧基苯基）丙烯酰胺（3k）被证明是hBChE最有效的抑制剂，IC 50为1.18± 1.31μM 。为了更好地了解最具活性的化合物对胆碱酯酶的酶-抑制剂相互作用，对高分辨率晶体学结构进行了分子建模研究。还评估了合成化合物对癌细胞系（肺癌）的抗癌作
• 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。
• Colorant compounds
  申请人：Banning H. Jeffrey

  公开号：US20060020141A1

  公开（公告）日：2006-01-26

  Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +y wherein y is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, Y, and z are as defined herein, Q − is a COO − group or a SO 3 — group, A is an organic anion, and CA is either a hydrogen atom or a cation associated with all but one of the Q − groups.

  式中的化合物，其中M是一个带有正电荷+y的金属离子，其中y是至少为2的整数，该金属离子能够与至少两个色团基团形成化合物，或者M是一个含金属基团的基团，能够与至少两个色团基团形成化合物，z是表示与金属相关的色团基团数量的整数，至少为2，R1、R2、R3、R4、R5、R6、R7、a、b、c、d、Y和z的定义如上所述，Q-是一个COO-基团或SO3-基团，A是一个有机阴离子，CA是一个氢原子或与除一个Q-基团之外的所有Q-基团相关联的阳离子。
• [EN] VOLTAGE-GATED SODIUM CHANNEL BLOCKERS<br/>[FR] BLOQUEURS DES CANAUX SODIQUES VOLTAGE-DÉPENDANTS
  申请人：GLAXO GROUP LTD

  公开号：WO2013006596A1

  公开（公告）日：2013-01-10

  In general, the present invention relates to uses of voltage-gated sodium channel blocker compounds,, which include corresponding precursors, intermediates, monomers and dimers, corresponding pharmaceutical compositions, compound preparation and treatment methods for respiratory and respiratory tract diseases. In particular, the present invention also relates to methods and uses for treatment of respiratory or respiratory tract diseases, which comprises administering to a subject in need thereof an effective amount of a compound of the present invention.

  一般而言，本发明涉及使用电压门控钠通道阻滞剂化合物，包括相应的前体、中间体、单体和二聚体，相应的药物组合物，化合物制备和治疗方法，用于呼吸和呼吸道疾病。具体而言，本发明还涉及用于治疗呼吸或呼吸道疾病的方法和用途，包括向需要的受试者施用本发明化合物的有效量。

表征谱图