2-氯-n-(2,6-二氯苯基)乙酰胺 | 3644-56-2

• 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: 2-氯-n-(2,6-二氯苯基)乙酰胺
• 中文别名: 2-氯-N-(2,6-二氯苯基)乙酰胺
• 英文名称: 2-chloro-N-(2,6-dichlorophenyl)acetamide
• 英文别名: N-(2,6-dichlorophenyl)-2-chloroacetamide；[(2,6-dichlorophenyl)aminocarbonylmethyl]chloride
• CAS: 3644-56-2
• 化学式: C₈H₆Cl₃NO
• mdl: MFCD00044773
• 分子量: 238.501
• InChiKey: CZAFLRAOEDDMCS-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C(Solv: ethanol (64-17-5))
• 沸点：
  376.2±42.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924299090

SDS

Name:	2-Chloro-N-(2,6-Dichlorophenyl)-Acetamide 99% Material Safety Data Sheet
Synonym:	None Known.
CAS:	3644-56-2

Section 1 - Chemical Product MSDS Name: 2-Chloro-N-(2,6-Dichlorophenyl)-Acetamide 99% Material Safety Data Sheet
Synonym: None Known.

---

SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3644-56-2	2-Chloro-N-(2,6-Dichlorophenyl)-Acetam	99%	222-874-4

Hazard Symbols: C
Risk Phrases: 34

---

SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Causes burns.Corrosive. Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
Causes gastrointestinal tract burns. May cause perforation of the digestive tract. May cause cardiac disturbances. May cause central nervous system effects. May cause systemic effects.
Inhalation:
Inhalation of high concentrations may cause central nervous system effects characterized by nausea, headache, dizziness, unconsciousness and coma. Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. May cause cardiac abnormalities. May cause systemic effects.
Chronic:
Effects may be delayed.

---

SECTION 4 - FIRST AID MEASURES
Eyes:
Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

---

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. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray. Cool containers with flooding quantities of water until well after fire is out.

---

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:
Use only in a well-ventilated area. Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes.
Storage:
Keep container closed when not in use. Corrosives area.

---

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# 3644-56-2: 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:
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
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 178 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H6Cl3NO
Molecular Weight: 238.50

---

SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

---

SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 3644-56-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-N-(2,6-Dichlorophenyl)-Acetamide - 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
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: III

---

SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
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. WGK (Water Danger/Protection) CAS# 3644-56-2: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 3644-56-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 3644-56-2 is not listed on the TSCA inventory. It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #4 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氯-n-(2,6-二氯苯基)乙酰胺 在 三氯化铝 作用下， 以81.3%的产率得到1-(2,6-二氯苯基)-1,3-二氢-2H-吲哚-2-酮
  参考文献：
  名称：

  1-[2,6-D-二氯苯基]indolin-2-ones的合成及抗炎活性

  摘要：

  在该酸的衍生物（酯、酰胺、亚甲基上的取代产物等）中，大部分时间都在寻找伏打烯（2-（2,6-二氯苯胺基）苯乙酸钠）的抗炎类似物[I , 3, 6-8]。由于我们发现伏打烯在酸性试剂存在下容易环化得到 1-(2,6-二氯苯基)indo!in-2-one (I)，因此希望获得该化合物的一些衍生物，用于测试炎症活性。

  DOI：

  10.1007/bf00767397
• 作为产物：
  描述：

  氯乙酰氯 、 2,6-二氯苯胺 在 magnesium oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以89%的产率得到2-氯-n-(2,6-二氯苯基)乙酰胺
  参考文献：
  名称：

  饱和杂环，第172部分†。2,6-二取代的5,6,7,8-四氢吡啶并[4,3- d ]嘧啶衍生物的合成

  摘要：

  通过将丙烯酸甲酯添加到苄胺或α-氨基吡啶上，合成标题化合物，得到相应的二酯，例如。12，然后由后者进行Dieckmann缩合，得到酮酯13，将其与am和胍3，14缩合。通过氢解除去苄基并随后将所得化合物5中6位的氮原子烷基化，同时改变C-2上的取代基，得到了许多具有潜在生物学作用的产物；其中一些具有止痛和抗炎作用。

  DOI：

  10.1002/jhet.5570270708

文献信息

• 6-Bromo-2,3-Dioxoindolin Phenylacetamide Derivatives: Synthesis, Potent CDC25B, PTP1B Inhibitors and Anticancer Activity
  作者：Shui-Lian Zhao、Zhou Peng、Xing-Hua Zhen、Yan Han、Hai-Ying Jiang、You-Le Qu、Li-Ping Guan

  DOI：10.2174/1570180812666141219003209

  日期：2015.6.6

  A series of 6-bromo-2,3-dioxoindolin phenylacetamide derivatives was synthesized and evaluated for inhibitory activity against CDC25B and PTP1B. Most of the synthesized compounds showed potential inhibitory activities for CDC25B and PTP1B with compound 12 being the most potent (IC50=3.87 µmol/L and 2.98 µmol/L, respectively). Compound 12 also exhibited higher cytotoxic activity against three cancer cell lines (HeLa, A549 and HCT116). In addition, compound 12 delayed the potent tumor inhibitory activity in a colo205 xenograft model in vivo.

  合成了一系列6-溴-2,3-二氧吲哚苯乙酰胺衍生物，并评估了它们对CDC25B和PTP1B的抑制活性。大多数合成的化合物显示出对CDC25B和PTP1B具有潜在的抑制活性，其中化合物12的活性最强（IC50分别为3.87 µmol/L和2.98 µmol/L）。化合物12对三种癌细胞系（HeLa、A549和HCT116）也显示出较高的细胞毒活性。此外，化合物12在体内colo205异种移植模型中延迟了强效的肿瘤抑制活性。
• Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study
  作者：Weifeng Ma、Peng Chen、Xiansen Huo、Yufeng Ma、Yanhong Li、Pengcheng Diao、Fang Yang、Shengquan Zheng、Mengjin Hu、Wenwei You、Peiliang Zhao

  DOI：10.1016/j.ejmech.2020.112847

  日期：2020.12

  Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over

  基于我们先前的工作，我们报道了CA-4的52种新的基于三唑并噻二嗪的类似物的设计，合成和生物学评估，以及它们的初步结构-活性关系。在合成的化合物中，Iab被发现是最有效的衍生物，在体外具有IC 50值（从几位数到几位数纳摩尔），并且对正常人胚胎肾HEK-293细胞也表现出优异的选择性（IC 50 > 100μM ）。进一步的机理研究表明，Iab显着阻断微管蛋白聚合并破坏A549细胞的细胞内微管网络。此外，艾伯通过调节p-cdc2和cyclin B1的表达诱导G2 / M细胞周期阻滞，并通过上调裂解的PARP和caspase-3的表达以及下调Bcl-2引起细胞凋亡。重要的是，在体内，Iab有效抑制异种移植小鼠模型中A549肺癌的肿瘤生长，而没有明显的毒性迹象，从而证实了其作为有望用于癌症治疗的潜力。
• Process for the production of tertiary 2-haloacetamides
  申请人：Monsanto Company

  公开号：US04258196A1

  公开（公告）日：1981-03-24

  The disclosure herein relates to a novel process for producing tertiary 2-haloacetamides by reacting primary or secondary 2-haloacetamides with an agent capable of generating an anion of the primary or secondary 2-haloacetamide under base conditions and alkylating the anion of the 2-haloamide with an alkylating agent; said anion is generated, for example, by electrolysis or by metals, metal hydrides, fluorides, oxides, hydroxides, carbonates, phosphates, or alkoxides.

  本公开涉及一种通过将一次或二次2-卤代乙酰胺与能够在碱性条件下生成一次或二次2-卤代乙酰胺的负离子的试剂反应，并用烷基化试剂烷基化2-卤代酰胺的新型生产三级2-卤代乙酰胺的方法；例如，通过电解或金属、金属氢化物、氟化物、氧化物、氢氧化物、碳酸盐、磷酸盐或烷氧基生成所述负离子。
• An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Olena Savych、Sergey Pipko、Angelika Konovets、Maxim O. Platonov、Oleksandr V. Vasylchenko、Vasyl V. Hurmach、Oleksandr O. Grygorenko

  DOI：10.1021/acscombsci.7b00163

  日期：2018.1.8

  An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200–350, cLogP 1–3) was prepared. The success rate of the method was analyzed as a function of physicochemical parameters

  开发了一种通过原位生成的2,2,2-三氟乙基氨基甲酸酯与α-氨基酯反应平行合成乙内酰脲文库的方法。为了证明该方法的实用性，准备了根据铅样标准（MW 200–350，cLogP 1-3）设计的1158个乙内酰脲文库。分析了该方法的成功率与产品理化参数的关系，发现该方法可以被认为是用于铅导向合成的工具。通过合理设计，使用开发的方法进行平行合成，计算机模拟和体外筛选相结合的方法，发现了一种含乙内酰脲的超微摩尔主要分子，可作为Aurora激酶A抑制剂。
• Design, Synthesis, biological Evaluation, and molecular docking studies of novel Pyrazolo[3,4-d]Pyrimidine derivative scaffolds as potent EGFR inhibitors and cell apoptosis inducers
  作者：Farag F. Sherbiny、Ashraf H. Bayoumi、Ahmed M. El-Morsy、Mohamed Sobhy、Mohamed Hagras

  DOI：10.1016/j.bioorg.2021.105325

  日期：2021.11

  4-d]pyrimidine scaffold having an amide linker and substituted with phenyl moiety at the 5-position was more potent than those possessing azomethine methyl, azomethine proton and carbomethene linkers, which lead to significant decrease in antiproliferative activity. The most potent compounds were further selected and evaluated for their activities against epidermal growth factor receptor (EGFR) kinase

  一系列新型杂化吡唑并 [ 3,4-d ] 嘧啶衍生物被设计并以有用的产率化学合成。合成的化合物通过常规技术进行结构表征。所有新合成的化合物都进行了体外生物筛选，以确定它们对一组四种癌细胞系的抗增殖活性，即 HepG-2、MCF-7、HCT-116 和 Hela。细胞毒性的评价的结果表明，化合物14D是似乎是最突出的广谱的细胞毒活性和显著比用IC索拉非尼更有效的50的4.28的值，5.18，3.97，和9.85μM对四个细胞系（HepG2，Hela细胞， HCT-116 和 MCF-7）。此外，化合物15与作为对照药物的索拉非尼相比，对所有测试细胞系显示出有希望的抗增殖作用，IC 50值小于 11 µM。此外，结构药效特征表明，具有酰胺连接基并在 5-位被苯基部分取代的吡唑并[ 3,4-d ]嘧啶支架比具有甲基偶氮甲碱、偶氮甲碱质子和碳甲烯连接基的那些更有效，从而导致显着的抗增殖活性降低。 根据均相时间分辨荧光