2-氯-6-氟苯甲醛肟 | 443-33-4

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯甲醛系列
• 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-6-氟苯甲醛肟
• 英文名称: 2-chloro-6-fluorobenzaldehyde oxime
• 英文别名: 2-Chloro-6-fluorobenzaldoxime；N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine
• CAS: 443-33-4
• 化学式: C₇H₅ClFNO
• mdl: MFCD00837704
• 分子量: 173.574
• InChiKey: OBJHLLOVMKKXDI-UHFFFAOYSA-N

物化性质

• 熔点：
  129-133 °C(lit.)
• 沸点：
  238.0±30.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S26,37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  2928000090

SDS

Name:	2-Chloro-6-fluorobenzaldehyde oxime tech Material Safety Data Sheet
Synonym:
CAS:	443-33-4

Section 1 - Chemical Product MSDS Name:2-Chloro-6-fluorobenzaldehyde oxime tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
443-33-4	2-Chloro-6-fluorobenzaldehyde oxime		207-135-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

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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.

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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# 443-33-4: 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: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 133 - 134 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: C7H5ClFNO
Molecular Weight: 174

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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.
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# 443-33-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-6-fluorobenzaldehyde oxime - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 443-33-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 443-33-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 443-33-4 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

制备方法与用途

制备方法

主要用作医药抗生素和农药植物生长调节剂等原料合成的原料。

用途简介 用途

主要用作医药抗生素、农药以及植物生长调节剂等原料合成的原料。

反应信息

• 作为反应物：
  描述：

  2-氯-6-氟苯甲醛肟 在 水 、 氯 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 3-(2-氯-6-氟苯基)-5-甲基异恶唑-4-羧酸
  参考文献：
  名称：

  铜（I）催化的环加成反应合成1,2,3-三唑取代的异恶唑

  摘要：

  据报道，从各种苯甲醛（I）开始，合成了一系列包含N-取代的1,2,3-三唑（V）的3,5-二取代的异恶唑-4-羧酸酯。苯甲醛与羟胺硫酸氢盐进行肟化反应。随后，氯化，然后与乙酰乙酸甲酯缩合，并将所得的酯水解，得到相应的羧酸（II），其在用PCl 5氯化后得到相应的酰氯（III）。炔丙基化时的钴氧酰氯（III）得到炔丙基酯（IV），点击反应这些得到标题化合物（V）。

  DOI：

  10.1002/jhet.837
• 作为产物：
  描述：

  2-氯-6-氟-苯甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 2-氯-6-氟苯甲醛肟
  参考文献：
  名称：

  新型肉桂酸衍生物作为候选杀菌剂的发现

  摘要：

  天然产物的结构多样性衍生是发现新型绿色农药的重要而有效的方法。肉桂酸在植物中含量丰富，其无与伦比的结构赋予其各种优异的生物活性。设计合成了一系列新型肉桂肟酯，用于开发高抗真菌农药。系统研究了其抗真菌活性、构效关系和作用机制。化合物7i 、 7u 、 7v和7x表现出令人满意的对抗全芽孢杆菌变种的活性。小麦，50 μg/mL 时抑制率≥90%。化合物7z和7n表现出优异的抗苹果腐烂病和灰葡萄孢的活性，中位有效浓度(EC 50 )值分别为0.71和1.41 μg/mL。 200 μg/mL 的化合物7z对苹果腐烂病表现出 100% 的保护和治疗活性。 7n对番茄果实和叶片灰霉病的防效均>96%，优于市售杀菌剂啶酰菌胺或相似效果。此外，还建立了定量构效关系，以指导进一步设计更高活性的化合物。作用机制的初步结果表明， 7n处理会破坏细胞核和线粒体的功能，导致活性氧积累和细胞膜损伤。其主要生化机制可能是抑制真菌麦角甾醇的生物合成。

  DOI：

  10.1021/acs.jafc.3c05655

文献信息

• 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。
• Half‐Sandwich Guanidinate–Osmium(II) Complexes: Synthesis and Application in the Selective Dehydration of Aldoximes
  作者：Javier Francos、Pedro J. González‐Liste、Lucía Menéndez‐Rodríguez、Pascale Crochet、Victorio Cadierno、Javier Borge、Antonio Antiñolo、Rafael Fernández‐Galán、Fernando Carrillo‐Hermosilla

  DOI：10.1002/ejic.201501221

  日期：2016.1

  precursor [OsCl(µ-Cl)(6-p-cymene)}2] (1) with 4 equivalents of the corresponding guanidine (iPrHN)2C=NR (2a–m) at room temperature. The easily separable guanidinium chloride salts [(iPrHN)2C(NHR)]Cl (4a–m) were also formed in these reactions. The structures of 3a, 3d, and 3h were unequivocally confirmed by X-ray diffraction methods. Complexes 3a–m proved to be active in the catalytic dehydration of aldoximes

  新型胍盐-锇 (II) 配合物 [OsCl2-(N,N')-C(NR)(NiPr)NHiPr}(6-p-cymene)] [R = Ph (3a), 4-C6H4F ( 3b), 4-C6H4Cl (3c), 4-C6H4CF3 (3d), 3-C6H4CF3 (3e), 3,5-C6H3(CF3)2 (3f), 4-C6H4CN (3g), 4-C6H4Me (3h) , 3-C6H4Me (3i), 2-C6H4Me (3j), 4-C6H4tBu (3k), 2,6-C6H3iPr2 (3l), 2,4,6-C6H2Me3 (3m)] 已以高产率合成 (70 –88 %) 通过使用 4 当量的相应胍 (iPrHN)2C=NR (2a–) 处理二聚体前体 [OsCl(µ-Cl)(6-p-伞花烃)}2] (1) 的 THF 溶液m) 在室温下。在这些反应中也形成了易于分离的氯化胍盐 [(iPrHN)2C(NHR)]Cl
• [EN] HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC CONDITIONS AND DISORDERS<br/>[FR] MODULATEURS DU RÉCEPTEUR HORMONAL POUR LE TRAITEMENT D'ÉTATS ET DE TROUBLES MÉTABOLIQUES
  申请人：ARDELYX INC

  公开号：WO2018039386A1

  公开（公告）日：2018-03-01

  The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): (I), wherein L1, A, X1, X2, R1, R2, and R3 are described herein.

  这项发明涉及FXR的激活剂，可用于治疗自身免疫性疾病、肝病、肠道疾病、肾脏疾病、癌症以及FXR在其中发挥作用的其他疾病，其化学式为(I)：(I)，其中L1、A、X1、X2、R1、R2和R3如本文所述。
• Palladium(<scp>ii</scp>) complexes with a phosphino-oxime ligand: synthesis, structure and applications to the catalytic rearrangement and dehydration of aldoximes
  作者：Lucía Menéndez-Rodríguez、Eder Tomás-Mendivil、Javier Francos、Carmen Nájera、Pascale Crochet、Victorio Cadierno

  DOI：10.1039/c5cy00413f

  日期：——

  diffraction methods, were active in the catalytic rearrangement of aldoximes. In particular, using 5 mol% complex 1, a large variety of aldoximes could be cleanly converted into the corresponding primary amides at 100 °C, employing water as solvent and without the assistance of any cocatalyst. Palladium nanoparticles are the active species in the rearrangement process. In addition, when the same reactions

  的[的PdCl治疗2（COD）]（COD = 1,5-环辛二烯）用在二氯甲烷中1个2当量的2-（二苯基膦基）苯甲醛肟在室温下导致的[的PdCl选择性形成2 κ 2 - （P，ñ）-2-PH 2 PC 6 H ^ 4 CH NOH}]（1）和[钯κ 2 - （P，ñ）-2-PH 2 PC 6 H ^ 4 CH NOH} 2 ] [CL]图2（2）分别代表Pd（II）含有膦-肟配体的配合物。这些化合物的结构已通过X射线衍射法充分证实，在醛肟的催化重排中具有活性。尤其是，使用5摩尔％的络合物1，无需水或任何助催化剂的辅助，即可在100℃下将多种醛肟干净地转化为相应的伯酰胺。钯纳米粒子是重排过程中的活性物质。另外，当使用乙腈作为溶剂进行相同的反应时，观察到醛肟的选择性脱水以形成各自的腈。为了进行比较，还简要地评估了肟衍生的四环化合物的催化行为。
• Solution-phase combinatorial synthesis of isoxazolines and isoxazoles using [2+3] cycloaddition reaction of nitrile oxides
  作者：Kyung Ho Kang、Ae Nim Pae、Kyung Il Choi、Yong Seo Cho、Bong Young Chung、Jee Eun Lee、Sun Ho Jung、Hun Yeong Koh、Hee-Yoon Lee

  DOI：10.1016/s0040-4039(00)02180-8

  日期：2001.2

  An efficient way to construct a library of isoxazoles and isoxazolines was developed by solution-phase 1,3-dipolar cycloaddition reaction of nitrile oxides with olefins and alkynes followed by precipitation of the products as HCl salts.

  通过将腈氧化物与烯烃和炔烃进行溶液相1，3-偶极环加成反应，然后将产物沉淀为HCl盐，开发了一种构建异恶唑和异恶唑啉文库的有效方法。