N1-(3-氯苯基)-2-氯乙胺 | 2564-05-8

• 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: N1-(3-氯苯基)-2-氯乙胺
• 中文别名: 2-氯-N-(3-氯苯基)乙酰胺；N1-(3-氯苯基)-2-氯乙酰胺
• 英文名称: 2-chloro-N-(3-chlorophenyl)acetamide
• 英文别名: [(3-chlorophenyl)aminocarbonylmethyl]chloride
• CAS: 2564-05-8
• 化学式: C₈H₇Cl₂NO
• mdl: MFCD00018896
• 分子量: 204.056
• InChiKey: KNVBYGNINQITJC-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  365.0±27.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)
• 保留指数：
  1612

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 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
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090

SDS

Name:	N1-(3-chlorophenyl)-2-chloroacetamide 97% Material Safety Data Sheet
Synonym:	2,3'-Dichloroacetanilide3-Chloro-N-(chloroacetyl)aniliin
CAS:	2564-05-8

Section 1 - Chemical Product MSDS Name:N1-(3-chlorophenyl)-2-chloroacetamide 97% Material Safety Data Sheet
Synonym:2,3'-Dichloroacetanilide3-Chloro-N-(chloroacetyl)aniliin

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2564-05-8	N1-(3-Chlorophenyl)-2-chloroacetamide	97%	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# 2564-05-8: 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: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 93 - 95 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: C8H7Cl2NO
Molecular Weight: 189.67

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2564-05-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N1-(3-Chlorophenyl)-2-chloroacetamide - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 2564-05-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2564-05-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2564-05-8 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：

  N1-(3-氯苯基)-2-氯乙胺 在 ammonium hydroxide 作用下， 反应 6.0h， 以50%的产率得到2-amino-N-(3-chlorophenyl)acetamide
  参考文献：
  名称：

  用于阿尔茨海默氏病治疗的新型自然启发多功能分子的设计，合成和生物学评估。

  摘要：

  为了克服克服与天然产物有关的阿尔茨海默氏病管理的局限性并开发体内活性多功能胆碱能抑制剂的总体目标，我们着手开发阿魏酸类似物。进行了系统的SAR研究，以改善LogP值较低的类似物对阿魏酸对胆碱酯酶的抑制作用。酶抑制和动力学研究确定化合物7a为具有优先乙酰胆碱酯酶抑制作用的先导分子（AChE IC50 = 5.74±0.13μM; BChE IC50 = 14.05±0.10μM）与母体阿魏酸（20μM时AChE和BChE的抑制％ ，分别为15.19±0.59和19.73±0.91）。分子对接和动力学研究表明7a非常适合AChE和BChE的活性位点，与AChE中的关键残基Asp74，Trp286和Tyr337以及BChE中的Tyr128，Trp231，Leu286，Ala328，Phe329和Tyr341形成稳定而强的相互作用。在DPPH分析中发现化合物7a是有效的抗氧化剂（IC50 = 57

  DOI：

  10.1016/j.ejmech.2020.112257
• 作为产物：
  描述：

  3-氯苯胺 在 N,N-二异丙基乙胺 、 氯乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 以323 mg的产率得到N1-(3-氯苯基)-2-氯乙胺
  参考文献：
  名称：

  N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB from Pseudomonas aeruginosa

  摘要：

  同时抑制金属β-内酰胺酶（MBLs）和像拉斯B这样的毒力因子，如来自铜绿假单胞菌的，提供了一种对抗抗生素耐药病原体的新方法。

  DOI：

  10.1039/d1md00187f

文献信息

• Acetamides and benzamides that are useful in treating sexual dysfunction
  申请人：——

  公开号：US20040029887A1

  公开（公告）日：2004-02-12

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。
• 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。
• Discovery of a Potent Botulinum Neurotoxin A Inhibitor <scp>ZM299</scp> with Effective Protections in Botulism Mice
  作者：Jianxin Wang、Yuelin Wu、Deyan Luo、Chunlin Zhuang、Nianzhi Ning、Yanming Zhang、Zhili He、Jie Gao、Zhanying Hong、Xiguo Xv、Wannian Zhang、Tao Li、Zhenyuan Miao、Hui Wang

  DOI：10.1002/cjoc.202100681

  日期：2022.2

  Botulinum neurotoxins serotype A (BoNT/A) is the deadliest toxins known to humans and the "Category A" agent for bioterrorism. Over the past 20 years, significant efforts have been put forth to develop effective inhibitors of BoNT/A. Unfortunately, few identified inhibitors possess noteworthy efficacy against BoNT/A in vivo. Here, we performed a high-throughput virtual screening based on the structure-based

  肉毒杆菌神经毒素血清型 A (BoNT/A) 是人类已知的最致命的毒素，也是生物恐怖主义的“A 类”毒剂。在过去的 20 年里，人们付出了巨大的努力来开发 BoNT/A 的有效抑制剂。不幸的是，很少有已鉴定的抑制剂在体内对 BoNT/A 具有显着功效。在这里，我们基于基于结构的对接模拟进行了高通量虚拟筛选，发现了一种新型强效支架 2-硫烟酸盐，可抑制 BoNT/A 轻链 (LC)。然后，我们合成并优化了一系列新型 2-硫烟酸衍生物，并在体外和体内综合评估了它们对 BoNT/A的活性. 优化的化合物 ZM299 在原代神经元中有效表现出抗 BoNT/A 活性，并在体内对 BoNT/A 显示出显着的治疗效果，在致死剂量的 BoNT/一次曝光。这些发现表明，2-硫代亚硝酸盐是一种有前景的支架，可用于生产更有效的抗 BoNT/A 类似物，而化合物 ZM299 作为治疗肉毒杆菌中毒的候选药物值得进一步临床前评估。
• Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives
  作者：Prakashsingh M. Chauhan、Sandeep N. Thummar、Kishor H. Chikhalia

  DOI：10.1007/s13738-018-1324-0

  日期：2018.6

  AbstractThe novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently

  摘要分别通过各种2-氯-N-苯基乙酰胺和肉桂酰氯衍生物合成了吗啉棒状3取代香豆基乙酰胺和肉桂酰胺衍生物的新衍生物5a-5j和6a-6j。通过Vilsmeier-Haack反应使吗啉在4-羟基香豆素上脱环，然后形成亚胺，然后与各种2-氯-N-苯基乙酰胺和肉桂酰氯缩合，以提供所需的分子，从而产生了所需的基序。合成的分子通过各种光谱方法进行表征，即IR，1 H NMR，131 H NMR。已经评估了它们对各种细菌和真菌菌株的抗菌活性，并且还对所有新合成的类似物进行了计算研究。 图形概要
• Tail approach synthesis of novel benzenesulfonamides incorporating 1,3,4-oxadiazole hybrids as potent inhibitor of carbonic anhydrase I, II, IX, and XII isoenzymes
  作者：Vikas Sharma、Rajiv Kumar、Andrea Angeli、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1016/j.ejmech.2020.112219

  日期：2020.5

  3 nM. Further hCA XII was weakly inhibited by all the compounds with KI values ranging from 0.23 μM to 3.62 μM. Interestingly structure-activity relationship (SAR) study indicates that N-(3-nitrophenyl)-2-((5-(4-sulfamoylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetamide (4j) is a potent compound to be investigated further for antiglaucoma and antitumor activity. The chemistry of the nature of different substitutions

  设计和合成了两个新系列的 1,3,4-恶二唑苯磺酰胺杂化物3和4，具有 20 种新化合物，以评估它们作为 CAI 对 hCA I、II、IX 和 XII 的抑制潜力。 “尾部方法”策略已用于设计具有羰基和酰胺连接基的芳香族磺​​酰胺支架。化合物3g和4j对hCA I表现出优异的抑制活性，比参考药物AAZ好3.5个数量级(K I = 250 nM)。此外，化合物4j (K I = 7.9 nM) 有效抑制青光眼相关的 hCA II 亚型以及肿瘤相关的 hCA IX 亚型，K I = 16.3 nM。此外，所有化合物均对 hCA XII 产生微弱抑制，K I值范围为 0.23 μM 至 3.62 μM。有趣的是构效关系 (SAR) 研究表明 N-(3-硝基苯基)-2-((5-(4-氨磺酰基苯基)-1,3,4-恶二唑-2-基)硫代)乙酰胺 ( 4j ) 是一种有效的化合物，有待进一步研究其抗青光

表征谱图