2,4-二氯苯甲醛肟 | 56843-28-8

• 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: 2,4-二氯苯甲醛肟
• 中文别名: 2,4,5-三甲基苯甲酸
• 英文名称: 2,4-dichlorobenzaldoxime
• 英文别名: 2,4-dichlorobenzaldehyde oxime；N-[(2,4-dichlorophenyl)methylidene]hydroxylamine
• CAS: 56843-28-8
• 化学式: C₇H₅Cl₂NO
• mdl: MFCD00173694
• 分子量: 190.029
• InChiKey: ONJQBRVMFRQQIG-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  271.3±30.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 储存条件：
  室温

SDS

Name:	2 4-Dichlorobenzaldehyde oxime 97% Material Safety Data Sheet
Synonym:
CAS:	56843-28-8

Section 1 - Chemical Product MSDS Name:2 4-Dichlorobenzaldehyde oxime 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
56843-28-8	2,4-Dichlorobenzaldehyde oxime	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# 56843-28-8: 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: 134 - 136 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: C7H5Cl2NO
Molecular Weight: 190.03

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 56843-28-8: CU5610500 LD50/LC50:
Not available.
Carcinogenicity:
2,4-Dichlorobenzaldehyde oxime - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

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# 56843-28-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 56843-28-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 56843-28-8 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：

  2,4-二氯苯甲醛肟 在 poly(diselanediyl-1,2-phenylene) 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 145.0h， 以98%的产率得到2,4-二氯苯甲酸
  参考文献：
  名称：

  ONE-POT OXIDATION OF AZOMETHINE COMPOUNDS INTO ARENECARBOXYLIC ACIDS

  摘要：

  Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.

  DOI：

  10.1081/scc-100105891
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 2,4-二氯苯甲醛肟
  参考文献：
  名称：

  14-脱氧-11,12-二脱氢穿心莲内酯 (14-DDA) 的 C-8 螺异恶唑啉类似物的设计和合成，用于 CDK4 和 BCL2 介导的抗癌活性的双重靶向

  摘要：

  14-脱氧-11,12-二脱氢穿心莲内酯 (14-DDA, ) 是一种在 中发现的次级代谢产物，已被合成修饰成一系列新的 C-8 螺异恶唑啉衍生物。穿心莲内酯及其衍生物的抗癌活性已得到充分报道，因此在此我们合成了 C-8 螺异恶唑啉衍生物 () 并筛选了针对四种人类癌细胞系的研究：乳腺癌 (MCF-7)、肺 (A549)、胰腺 ( MiaPaCa-2) 和前列腺 (PC-3)。大多数合成的化合物对不同的人类癌症系表现出比母体天然产物穿心莲内酯（）和14-脱氧-11,12-二脱氢穿心莲内酯（）更好的抗癌活性。在所有化合物中，该化合物对乳腺癌细胞 (MCF-7) 显示出最强的细胞毒性 (IC = 3 μM)。此外，机理研究表明，该化合物影响 MCF-7 细胞的核形态，增加细胞和线粒体 ROS 的产生，降低线粒体膜电位 (MMP)，并抑制集落形成。该化合物还通过以剂量依赖性方式减弱 BCl2 表达来诱导

  DOI：

  10.1016/j.molstruc.2023.137072

文献信息

• Terminal Alkyne-Assisted One-Pot Synthesis of Arylamidines: Carbon Source of the Amidine Group from Oxime Chlorides
  作者：Fengping Yi、Qihui Sun、Jing Sun、Chao Fu、Weiyin Yi

  DOI：10.1021/acs.joc.9b00538

  日期：2019.6.7

  a diverse range of arylamidines from a novel cascade reaction of in situ generated nitrile oxides, sulfonyl azides, terminal alkynes, and water by [3 + 2] cycloaddition and ring opening sequence was developed. The use of aryl oxime chlorides as the carbon source of the amidine group and the addition of water proved to be critical for the reaction. Moreover, terminal alkynes, which can lead to high yields

  终端炔烃辅助方案可通过[3 + 2]环加成和开环顺序一锅法生成原位生成的腈氧化物，磺酰叠氮化物，终端炔烃和水的新型级联反应，从而一锅式形成多种芳基胺。发达。使用芳基肟氯化物作为am基的碳源并添加水对于反应至关重要。而且，末端炔烃可以通过使用较少量而导致高产率的产物，可以在反应中起催化作用。研究了更广泛的基材。
• Ruthenium-Catalyzed Rearrangement of Aldoximes to Primary Amides in Water
  作者：Rocío García-Álvarez、Alba E. Díaz-Álvarez、Javier Borge、Pascale Crochet、Victorio Cadierno

  DOI：10.1021/om3006917

  日期：2012.9.10

  The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η6-C6Me6)P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70–90%) after short reaction times (1–7 h). The process was operative with both aromatic

  醛肟于伯酰胺的重排已使用容易获得的芳烃-钌（II）络合物将[RuCl研究2（η 6 -C 6我6）P（NME 2）3 }]（5摩尔％）作为催化剂。反应在纯水中于100°C干净地进行，无需任何助催化剂的帮助，在较短的反应时间（1-7小时）后，以高收率（70-90％）得到所需的酰胺。该方法对芳香族，杂芳香族，α，β-不饱和和脂肪族醛肟均有效，并能耐受多个官能团。使用18的反应曲线和实验O标记的水表明在这些转化中涉及两种不同的机制。在两者中，腈中间体最初都是通过醛肟的脱水而形成的。然后通过醛肟或水的第二分子的作用将这些中间体水合为相应的酰胺。还讨论了苯甲醛肟重排成苯甲酰胺的动力学分析。
• TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
  作者：Jalil Noei、Ahmad R. Khosropour

  DOI：10.1016/j.tetlet.2008.09.084

  日期：2008.12

  The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.

  发现TiCl 3 OTf与1-丁基-3-甲基咪唑鎓溴化物的组合是一种高效新颖的催化系统，用于以高产率至优异产率将芳基醛肟化学选择性地一锅转化为相应的硫代酰胺。
• [EN] NOVEL MICROBIOCIDES<br/>[FR] NOUVEAUX MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2009127726A1

  公开（公告）日：2009-10-22

  Compounds of formula (I) in which the substituents are as defined in claim 1, are suitable for use as microbiocides.

  公式(I)中的化合物，其中取代基如权利要求1中定义，适用于作为微生物杀灭剂使用。
• Synthesis and biological activity of 3-substituted isoxazolecarboxamides
  作者：Mirosław Gucma、W. Marek Gołębiewski

  DOI：10.1007/s00706-010-0265-9

  日期：2010.4

  AbstractA series of novel 3-substituted isoxazolecarboxamides have been prepared. A key step was 1,3-dipolar cycloaddition of nitrile oxides to α,β-unsaturated esters. Some of these compounds exhibited high fungicidal activities against Alternaria alternata, Botrytis cinerea, Rhizoctonia solani, Fusarium culmorum, and Phytophthora cactorum. Graphical abstract

  摘要已经制备了一系列新颖的3-取代的异恶唑羧酰胺。关键步骤是将腈氧化物与α，β-不饱和酯进行1,3-偶极环加成。这些化合物的一些表现出对高杀真菌活性孢 孢，灰葡萄 孢，立枯丝核 菌，尖镰 孢，和疫霉 恶疫霉。 图形概要