2-氯乙酰苯胺 | 587-65-5

• 物质功能分类: 有机原料 - 氨基化合物
• 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: 2-氯乙酰苯胺
• 中文别名: 2-氯-N-苯基乙酰胺；2ˊ-氯乙酰苯胺
• 英文名称: N-chloroacetyl-aniline
• 英文别名: 2-chloro-N-phenylacetamide；2-Chloroacetanilide
• CAS: 587-65-5
• 化学式: C₈H₈ClNO
• mdl: MFCD00018887
• 分子量: 169.611
• InChiKey: VONWPEXRCLHKRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C (lit.)
• 沸点：
  340.0±25.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 颜色/状态：
  Very light beige, crystalline powder
• 稳定性/保质期：
  在常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 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

ADMET

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为继发性毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 非人类毒性摘录

2-氯-N-苯基乙酰胺显示出相对较弱的胆碱乙酰转移酶抑制活性。

2-CHLORO-N-PHENYLACETAMIDE SHOWED RELATIVELY WEAK CHOLINE ACETYLTRANSFERASE INHIBITION ACTIVITY.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

氯乙酰苯胺（2-CAA）、3-氯乙酰苯胺（3-CAA）和4-氯乙酰苯胺（4-CAA）对大鼠肝肾功能和形态的影响进行了研究。Fischer 344雄性大鼠单次腹腔注射氯乙酰苯胺，剂量为0.5、1.0或1.5毫摩尔/千克。在给药后的24或48小时内监测肾功能。在24或48小时时，确定肝功能和组织形态。在两个较低剂量水平上，所有三种氯乙酰苯胺异构体在治疗后第一天减少了食物和水的摄入量。食物摄入量在2-CAA和3-CAA处理的动物在第二天仍然下降，但水的摄入量正常。只有在4-CAA处理的大鼠中，第一天尿蛋白排泄量增加。在任何一组中，48小时内的血尿素氮浓度都没有增加，而只有在3-CAA处理组中肾脏重量增加。在3-CAA和4-CAA处理的大鼠中，48小时时肝脏重量增加。血浆丙氨酸转氨酶活性仅在4-CAA组在48小时时增加。在额外的研究中，将未处理的大鼠肾皮质切片与氯乙酰苯胺或载体一起孵化，并确定对有机离子积累的影响。研究显示氯乙酰苯胺以异构体特异性的方式直接改变肾功能。

The effects of 2-chloroacetanilide (2-CAA), 3-chloroacetanilide (3-CAA) and 4-chloroacetanilide (4-CAA) on liver and kidney function and morphology were examined in rats. Male Fischer 344 rats were given a single ip injection of a chloroacetanilide at 0.5, 1.0 or 1.5 millimole/kg. Renal function was monitored for 24 or 48 hr following dosing. At 24 or 48 hr, liver function and tissue morphology were determined. At the two lower dose levels,all three chloroacetanilide isomers decr food and water intake on day 1 after treatment. Food intake remained depressed in 2-CAA and 3-CAA treated animals on the second day, but water intake was normal. Urinary protein excretion on day 1 was incr only in rats treated with 4-CAA. Blood urea nitrogen concn was not incr in any group at 48 hr while kidney weight was incr only in the 3-CAA treated group. Hepatic weight was incr at 48 hr in rats treated with 3-CAA and 4-CAA. Plasma alanine aminotransferase activity was incr at 48 hr only in the 4-CAA group. In additional studies, renal cortical slices from untreated rats were incubated with a chloroacetanilide or vehicle and the effect on organic ion accumulation was determined. Chloroacetanilides were shown to directly alter renal function in an isomer specific manner.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• RTECS号：
  AE1000000
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下应存于密封、避光、通风干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloroacetanilide
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Chloroacetanilide
CAS number: 587-65-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8ClNO
Molecular weight: 169.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氯乙酰苯胺 在 盐酸 、 乙醇 作用下， 生成 2-氨基甲酰基硫基-N-苯基-乙酰胺
  参考文献：
  名称：

  Beckurts; Frerichs, Journal fur praktische Chemie (Leipzig 1954), 1902, vol. <2>66, p. 180

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-N-苯基乙酰胺 在 氯化亚砜 作用下， 生成 2-氯乙酰苯胺
  参考文献：
  名称：

  Iwamoto; Farson, Journal of the American Pharmaceutical Association (1912), 1946, vol. 35, p. 50

  摘要：

  DOI：
• 作为试剂：
  描述：

  7-甲基-4-羟基-9-甲氧基-5H-呋喃并[3,2-g][1]苯并吡喃-5-酮 在 potassium carbonate 、 2-氯乙酰苯胺 、 丙酮 作用下， 生成 (9-methoxy-7-methyl-5-oxo-5H-furo[3,2-g]chromen-4-yloxy)-acetic acid anilide
  参考文献：
  名称：

  Musante, Annali di Chimica, 1956, vol. 46, p. 768,779

  摘要：

  DOI：

文献信息

• Synthesis of novel 1,2-benzothiazine 1,1-dioxide-3-ethanone oxime N-aryl acetamide ether derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage transformation
  作者：Malla Reddy Gannarapu、Sathish Babu Vasamsetti、Nagender Punna、Naresh Kumar Royya、Shanthan Rao Pamulaparthy、Jagadeesh Babu Nanubolu、Srigiridhar Kotamraju、Narsaiah Banda

  DOI：10.1016/j.ejmech.2013.12.053

  日期：2014.3

  A series of novel 1,2-benzothiazine 1,1-dioxide-3-ethanone oxime N-aryl acetamide ether derivatives 7a–h and 9a–h were synthesized starting from sodium salt of saccharin 1 in series of steps. Final compounds 7a–h and 9a–h were evaluated for the anti-inflammatory activity and their ability to inhibit monocyte-to-macrophage transformation. Compounds 7e, 9b, 9e and 9h showed impressive anti-inflammatory

  从糖精1的钠盐开始，按一系列步骤合成了一系列新颖的1,2-苯并噻嗪1,1-二氧化物-3-乙酮肟N-芳基乙酰胺醚衍生物7a – h和9a – h。评价了最终化合物7a – h和9a – h的抗炎活性及其抑制单核细胞向巨噬细胞转化的能力。化合物7e，9b，9e和9h在微摩尔浓度下显示出令人印象深刻的抗炎活性（TNF-α，IL-8和MCP-1），被发现比阳性对照（吡罗昔康）更好。化合物9e和化合物9h均显着抑制PMA诱导的MMP-9明胶酶活性。化合物9e和9h也极大地抑制了PMA诱导的单核细胞向巨噬细胞的转化，这是形成动脉粥样硬化的必要步骤。
• 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。
• Microwave-Assisted Preparation of Fused Bicyclic Heteroaryl Boronates:  Application in One-Pot Suzuki Couplings
  作者：Erin F. DiMauro、Jason R. Vitullo

  DOI：10.1021/jo060218p

  日期：2006.5.1

  The rapid and efficient synthesis of various disubstituted 5,6-fused heterocycles using a microwave-assisted one-pot cyclization−Suzuki coupling approach is described. This work highlights the tolerance of the boronic ester functional group to a variety of reaction conditions and the utility of functionalized boronates as penultimate intermediates in the synthesis of diverse compound libraries.

  描述了使用微波辅助的一锅环化-Suzuki偶联方法快速有效地合成各种二取代的5,6-稠合杂环的方法。这项工作强调了硼酸酯官能团对各种反应条件的耐受性以及官能化的硼酸盐作为倒数第二种中间体在各种化合物库的合成中的用途。
• [EN] COMPOUNDS MODULATING PROTEIN RECRUITMENT AND/OR DEGRADATION<br/>[FR] COMPOSÉS MODULANT LE RECRUTEMENT ET/OU LA DÉGRADATION DE PROTÉINES
  申请人：ORIONIS BIOSCIENCES INC

  公开号：WO2021126973A1

  公开（公告）日：2021-06-24

  The invention provides cereblon binders for the degradation of proteins by the ubiquitin proteasome pathway for therapeutic applications.

  这项发明提供了用于通过泛素蛋白酶体途径降解蛋白质的 cereblon 结合物，用于治疗应用。
• 5‐(4‐Methoxybenzylidene)thiazolidine‐2,4‐dione‐derived VEGFR‐2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations
  作者：Khaled El‐Adl、Helmy Sakr、Mohamed Nasser、Mohamed Alswah、Fatma M. A. Shoman

  DOI：10.1002/ardp.202000079

  日期：2020.9

  4‐dione derivatives, 5a–g and 7a–f, was designed, synthesized, and evaluated for their anticancer activity against HepG2, HCT116, and MCF‐7 cells. HepG2 and HCT116 were the most sensitive cell lines to the influence of the new derivatives. In particular, compounds 7f, 7e, 7d, and 7c were found to be the most potent derivatives of all the tested compounds against the HepG2, HCT116, and MCF‐7 cancer cell

  设计、合成了一系列新型 5-(4-甲氧基亚苄基)噻唑烷-2,4-二酮衍生物，5a-g 和 7a-f，并评估了它们对 HepG2、HCT116 和 MCF-7 细胞的抗癌活性。HepG2 和 HCT116 是对新衍生物影响最敏感的细胞系。特别是，发现化合物 7f、7e、7d 和 7c 是所有测试化合物中对抗 HepG2、HCT116 和 MCF-7 癌细胞系最有效的衍生物。化合物 7f（分别为 IC50 = 6.19 ± 0.5、5.47 ± 0.3 和 7.26 ± 0.3 µM）对 M 和 CFp2 的活性分别高于索拉非尼（IC50 = 9.18 ± 0.6、8.37 ± 0.7 和 5.10 ± 0.4 µM） ‐7, 细胞，但对 HCT116 癌细胞的活性较低。此外，该化合物显示出比阿霉素更高的活性（IC50 = 7.94 ± 0.6、8.07 ± 0.8 和 6.75 ± 0。分别为

表征谱图