N1-(2,4-二氯苯基)苯甲酰胺 | 10286-76-7

• 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-(2,4-二氯苯基)苯甲酰胺
• 英文名称: 2',4'-Dichlorobenzanilide
• 英文别名: N-(2,4-dichlorophenyl)benzamide；benzoic acid-(2,4-dichloro-anilide)；Benzoesaeure-(2,4-dichlor-anilid)；Benzoesaeure-[2.4-dichlor-anilin
• CAS: 10286-76-7
• 化学式: C₁₃H₉Cl₂NO
• mdl: MFCD00018345
• 分子量: 266.127
• InChiKey: ZRTPCLPWDMPXBB-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  300.4±32.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2927000090

SDS

Name:	N1-(2 4-dichlorophenyl)benzamide 97% Material Safety Data Sheet
Synonym:	N-Benzoyl-2,4-dichloroaniline2',4'-Dichlorobenzanilid
CAS:	10286-76-7

Section 1 - Chemical Product MSDS Name:N1-(2 4-dichlorophenyl)benzamide 97% Material Safety Data Sheet
Synonym:N-Benzoyl-2,4-dichloroaniline2',4'-Dichlorobenzanilid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10286-76-7	N1-(2,4-Dichlorophenyl)benzamide	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

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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.
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.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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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.

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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.

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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# 10286-76-7: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C13H9Cl2NO
Molecular Weight: 266

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10286-76-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N1-(2,4-Dichlorophenyl)benzamide - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 10286-76-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10286-76-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10286-76-7 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：

  N1-(2,4-二氯苯基)苯甲酰胺 在 溶剂黄146 、 calcium chloride 作用下， 生成 benzoic acid-(2,4,N-trichloro-anilide)
  参考文献：
  名称：

  Chattaway; Orton, Journal of the Chemical Society, 1899, vol. 75, p. 1050

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-氯-苯基)-苯酰胺 在 四丁基氢氧化铵 、 1,2-二氯乙烷 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以84%的产率得到N1-(2,4-二氯苯基)苯甲酰胺
  参考文献：
  名称：

  用1,2-二氯乙烷制备（杂）芳基氯化物和氯乙烯的高效电催化。

  摘要：

  尽管在有机合成中同时使用1,2-二氯乙烷（DCE）作为氯化试剂，同时释放出氯乙烯作为有用的副产物是一个绝妙的主意，但由于其存在的挑战，它仍然提出了巨大的挑战，但尚未实现。苛刻的脱氯化氢条件和缓慢的CH氯化过程。在这里，我们报告了一种双功能电催化策略，用于在阴极处DCE的催化脱氯化氢，同时使用释放的HCl作为氯化物来源进行阳极氧化芳族氯化，以有效合成增值的（杂）芳基氯化物。该协议的温和性和实用性通过生物活性分子的高效后期氯化进一步得到了证明。

  DOI：

  10.1002/anie.201814570

文献信息

• Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon
  作者：Jian-Quan Liu、Xuanyu Shen、Zhenhua Liu、Xiang-Shan Wang

  DOI：10.1039/c7ob01449j

  日期：——

  An interesting radical coupling reaction of aromatic aldehydes with isocyanides was disclosed for the synthesis of amides catalyzed by copper. According to the experimental results and mechanistic study, the isocyano group acted as an N1 synthon rather than exhibiting the carbene-like reactivity, exploiting a new reactivity profile of isocyanides.

  公开了一种有趣的芳族醛与异氰酸酯的自由基偶联反应，用于合成铜催化的酰胺的合成。根据实验结果和机理研究，异氰酸酯基团起N1合成子的作用，而不是表现出卡宾样的反应性，从而利用了异氰酸酯的新反应性特征。
• The mechanisam of electrochemical reduction of <i>N</i>-haloamides in acetonitrile: trapping of intermediate amide anions and father–son protonation
  作者：Denis Bérubé、Jean Lessard

  DOI：10.1139/v82-168

  日期：1982.5.1

  The electrochemical reduction of N-haloamides (ZCONRX) in acetonitrile involves two consecutive one-electron transfers and generates the amide anion. Attempts to trap the intermediate amidyl radical resulting from the first electron transfer were unsuccessful. In the case of the N-halo-N-hydroamides (R = H), the amide anion formed at the electrode abstracts a proton from an incoming N-halo-N-hydroamide molecule to give the parent amide and the conjugate base of the N-haloamide (father–son protonation). Thus, half of the N-halo-N-hydroamide reaching the electrode is reduced, the other half being converted to its conjugate base. In acetonitrile-LiClO₄ (0.2 M) containing 0.2% water, the conjugate base is reducible and the polarograms therefore show two waves (irreversible and diffusion controlled) of equivalentintensities due respectively to the reduction of the N-halo-N-hydroamide and to the reduction of its conjugate base. In the case of the N-chloro-N-alkyl(aryl)amides (X = Cl, R = alkyl or aryl), the amide anion abstracts a proton from the medium to give the parent amide and anionic species that react with the starting N-chloroamide regenerating the amide anion. Hence, the coulometric results are low [Formula: see text] However, in the presence of acetic acid, the reduction consumes 2 F/mol as expected. The N-alkylamide anion has been trapped by N-alkylation and N-acylation. The voltammograms of N-chloro-N-alkyl(aryl)amides show multiple waves on mercury and platinum due to passivation–adsorption phenomena but a single wave on vitreous carbon.

  在乙腈中，N-卤代酰胺（ZCONRX）的电化学还原包括两个连续的单电子转移，并生成酰胺负离子。试图捕获由第一个电子转移产生的中间酰基自由基的尝试未成功。在N-卤代-N-羟酰胺（R = H）的情况下，电极上形成的酰胺负离子从进入的N-卤代-N-羟酰胺分子中提取一个质子，从而形成母酰胺和N-卤代酰胺的共轭碱（父子质子化）。因此，达到电极的N-卤代-N-羟酰胺的一半被还原，另一半被转化为其共轭碱。在含0.2%水的乙腈-LiClO4（0.2 M）中，共轭碱可被还原，因此极谱图显示了两个波（不可逆和扩散控制），分别由于N-卤代-N-羟酰胺的还原和其共轭碱的还原而产生等强度。在N-氯代-N-烷基（芳基）酰胺（X = Cl，R = 烷基或芳基）的情况下，酰胺负离子从介质中提取一个质子，形成母酰胺和与起始N-氯代酰胺反应的阴离子物种，再生酰胺负离子。因此，库仑计量结果较低。然而，在存在乙酸的情况下，还原消耗2 F/mol，符合预期。N-烷基酰胺负离子已通过N-烷基化和N-酰化进行捕获。N-氯代-N-烷基（芳基）酰胺的伏安图在汞和铂上显示多个波，由于钝化-吸附现象，但在玻璃碳上只显示单个波。
• Aminolysis of allyl esters with bislithium aryl amides
  作者：Catherine A. Faler、Madeleine M. Joullié

  DOI：10.1016/j.tetlet.2006.07.136

  日期：2006.10

  The aminolysis of allyl esters with bislithium amides is reported. Tertiary aryl amides were synthesized in a one-pot reaction with bislithium amides and a suitable electrophile in good yields. The scope of this reaction was demonstrated with a variety of anilines and aminopyridines and applied to the synthesis of triphenylmethylacetamides.

  报道了烯丙基酯与双锂酰胺的氨解。叔芳基酰胺与双锂酰胺和合适的亲电试剂通过一锅法合成，收率很高。用各种苯胺和氨基吡啶证明了该反应的范围，并将其用于三苯基甲基乙酰胺的合成。
• Amide-assisted radical strategy: metal-free direct fluorination of arenes in aqueous media
  作者：Deqiang Liang、Yanni Li、Shulin Gao、Renlun Li、Xiangguang Li、Baoling Wang、Hai Yang

  DOI：10.1039/c7gc00356k

  日期：——

  A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho–para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities

  在酰胺基团的帮助下，开发了无金属和无引发剂的芳烃直接氟化方法。该反应在简单的水性条件下进行，具有良好的官能团耐受性和邻位-对位选择性，并且非常实用，因为它很容易按比例放大至几克规模。在这一阶段，尚不能提出排他的机制，并且已经讨论了几种可能性。实验和计算研究以及开创性的工作都支持了酰胺辅助的自由基链机理的可能性。
• Prevention of Diabetes in the NOD Mouse by Intra-muscular Injection of Recombinant Adeno-associated Virus Containing the Preproinsulin II Gene
  作者：Rahul M. Jindal、M. Karanam、Rita Shah

  DOI：10.1155/edr.2001.129

  日期：——

  Using the Adeno-associated virus (AAV) as a gene delivery vehicle, we have constructed a recombinant vector containing the full length rat preproinsulin gene (vLP-1). Utilizing the well described non-obese diabetic (NOD) mouse model, an experimental group (n=10) of animals were intramuscularly (IM) injected with107rAAV virions containing the insulin gene and compared to a mock-injected control group (n=10). Blood glucose (glc) was then measured weekly for 16 weeks. Data showed that the experimental group contained 70% euglycemic animals (defined as glc <200mg/dL)versus10% of the control animals (P<.05) at 14 weeks. Mean weight in the treated group was greater than the untreated group. Insulin mRNA was detected at the injection site of all of the treated animals, but not controls. Complete destruction of islets was confirmed by histology ruling out the possibility of spontaneous reversal of insulinitis. We conclude that IM delivery of the insulin gene in the NOD mouse was able to prevent clinical DM up to 14 weeks in a majority of treated animals. Our experimental data suggests that gene therapy may be an alternative treatment for IDDM in the future.

  我们利用腺相关病毒（AAV）作为基因递送载体，构建了一种含有全长大鼠前胰岛素基因（vLP-1）的重组载体。利用已被充分描述的非肥胖糖尿病（NOD）小鼠模型，向实验组（n=10）动物肌肉注射含有胰岛素基因的 107rAAV 病毒，并与模拟注射对照组（n=10）进行比较。然后每周测量血糖（glc），持续 16 周。数据显示，14 周时，实验组有 70% 的动物出现优生（定义为 glc <200mg/dL），而对照组只有 10% 的动物出现优生（P<.05）。治疗组的平均体重高于未治疗组。在所有治疗组动物的注射部位都检测到了胰岛素 mRNA，而对照组没有检测到。组织学检查证实了胰岛的完全破坏，排除了胰岛素炎自发逆转的可能性。我们得出的结论是，在 NOD 小鼠体内注射胰岛素基因能够预防大多数治疗动物的临床 DM，最长可达 14 周。我们的实验数据表明，基因疗法可能是未来治疗 IDDM 的一种替代疗法。

表征谱图