3-双邻氯苯基-5-甲基-4-异恶唑酰氯 | 4462-55-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酰卤
• 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: 3-双邻氯苯基-5-甲基-4-异恶唑酰氯
• 中文别名: 双氯西林酰氯；3-(2,6-二氯苯基)-5-甲基异噁唑-4-甲酰氯；双氯酰氯；3-(2,6-二氯苯基)-5-甲基异恶唑-4-碳酰氯；3-(2,6-二氯苯基)-5-甲基异唑-4-甲酰氯
• 英文名称: 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride
• 英文别名: 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride；3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl chloride
• CAS: 4462-55-9
• 化学式: C₁₁H₆Cl₃NO₂
• mdl: MFCD00051658
• 分子量: 290.533
• InChiKey: IZQGELJKDARDMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C
• 沸点：
  390.9±42.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)
• LogP：
  3.26 at 25℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 危险品运输编号：
  UN 3261
• 海关编码：
  2934999090
• 储存条件：
  室温

SDS

Name:	3-(2 6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride 97% Material Safety Data Sheet
Synonym:
CAS:	4462-55-9

Section 1 - Chemical Product MSDS Name:3-(2 6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4462-55-9	3-(2,6-Dichlorophenyl)-5-methylisoxazo	97%	224-723-8

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under nitrogen.

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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# 4462-55-9: 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: off-white - pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 94 - 96 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: C11H6Cl3NO2
Molecular Weight: 291

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases, alcohols.
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# 4462-55-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
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.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4462-55-9: No information available.
Canada
CAS# 4462-55-9 is listed on Canada's NDSL List.
CAS# 4462-55-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4462-55-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途
用作医药中间体，具体为双氯苯唑青霉素钠的中间体。

生产方法
首先，使用2,6-二氯甲苯在紫外线催化下与氯气和三氯化磷反应生成2,6-α,α-四氯甲苯。接着，在浓硫酸参与下，2,6-二氯甲苯与盐酸羟胺肟化得到2,6-二氯苯甲肟；再经过氯化步骤产生2,6-二氯苯甲肟氯。随后，将2,6-二氯苯甲肟氯与乙酰乙酸乙酯在氢氧化钠的作用下环合生成3-(2,6-二氯苯基)-5-甲基-4-异噁唑甲酸乙酯；最后通过酯基水解，并利用五氯化磷对羧基进行氯化，从而制得目标产品。

反应信息

• 作为反应物：
  描述：

  3-双邻氯苯基-5-甲基-4-异恶唑酰氯 以 吡啶 、 乙二醇二甲醚 为溶剂， 生成 (4-{2-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonylamino]-ethyl}-benzenesulfonyl)-carbamic acid methyl ester
  参考文献：
  名称：

  Pluempe; Horstmann; Puls, Arzneimittel-Forschung/Drug Research, 1974, vol. 24, # 0, p. 363 - 374

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2,6-二氯苯基)-5-甲基异噁唑-4-羧酸甲酯 在 五氯化磷 、 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-双邻氯苯基-5-甲基-4-异恶唑酰氯
  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

文献信息

• INDANONE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS OR OPTICAL ISOMERS THEREOF, PREPARATION METHOD FOR SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING VIRAL DISEASES
  申请人：Jung Young Sik

  公开号：US20140114068A1

  公开（公告）日：2014-04-24

  Disclosed are novel indanone derivatives, pharmaceutically acceptable salts thereof or enantiomers, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of viral diseases, comprising the same as an active ingredient. The indanone derivatives have excellent inhibitory activity against picornaviruses including coxsackie-, entero-, echo-, Polio-, and rhinoviruses, as well as exhibiting low cytotoxicity, so that they can be useful as an active ingredient of a pharmaceutical composition for the prevention or treatment of viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular disease, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, herpangina, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.

  揭示了新颖的茚酮衍生物，其药用盐或对映体，以及其制备方法和作为活性成分的用于预防或治疗病毒性疾病的药物组合物。这些茚酮衍生物对包括柯萨奇病毒、肠道病毒、回声病毒、脊髓灰质炎病毒和鼻病毒在内的小RNA病毒具有出色的抑制活性，并且具有低细胞毒性，因此它们可用作预防或治疗包括小儿麻痹症、瘫痪、急性出血性结膜炎、病毒性脑膜炎、手足口病、水疱病、甲型肝炎、肌炎、心肌炎、胰腺炎、糖尿病、流行性肌痛、脑炎、流感、手足口病、哮喘、慢性阻塞性肺病、肺炎、鼻窦炎或中耳炎等病毒性疾病的药物组合物的活性成分。
• Structure–activity relationships of acyloxyamidine cytomegalovirus DNA polymerase inhibitors
  作者：John A. Tucker、Terrance L. Clayton、Connie G. Chidester、Martin W. Schulz、Leigh E. Harrington、Steven J. Conrad、Yoshihiko Yagi、Nancee L. Oien、David Yurek、Ming-Shang Kuo

  DOI：10.1016/s0968-0896(99)00319-3

  日期：2000.3

  initio molecular orbital calculations combined with qualitative estimates of steric interaction energies suggest that the lowest energy conformations of the acyloxyamidine linker are characterized by an extended planar CAr-C=N-O-C arrangement and either a syn-periplanar or anti-periplanar N-O-C-C(Ar') arrangement. Only the anti-periplanar conformation was observed in the crystal structures of three

  本文描述了新型的巨细胞病毒DNA聚合酶抑制剂的结构活性关系，该抑制剂具有两个通过酰氧基oxy连接子连接的芳基。对其中末端基团不同的一系列类似物的研究表明，在先导化合物的2,4-二氯苯基周围有非常窄的SAR，但苯并噻唑环的各种替代物均具有活性。其中最引人注目的是化合物78的异恶唑环，与先导化合物相比，其效价提高了30倍。我们还描述了10个类似物的设计，合成和评估，其中酰氧基am连接基被等位基团修饰或替代。结构-活性关系研究确定了接头-NH2基团是关键的药效学元素。从头算分子轨道计算与对空间相互作用能的定性估计相结合，表明酰氧基am连接子的最低能构象具有扩展的平面CAr-C = NOC排列以及同平面或反平面NOCC（Ar'）安排。在三个酰氧基am的晶体结构中仅观察到反平面构象。在这些研究的基础上设计的最有效的连接基修饰化合物是氨基甲酸20 20，在巨细胞病毒DNA聚合酶抑制试验中，氨基甲酸am的含量约为对照酰氧基am
• Discovery of <i>N</i>-Aroyl Diketone/Triketone Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibiting-Based Herbicides
  作者：Ying Fu、Dong Zhang、Shuai-Qi Zhang、Yong-Xuan Liu、You-Yuan Guo、Meng-Xia Wang、Shuang Gao、Li-Xia Zhao、Fei Ye

  DOI：10.1021/acs.jafc.9b01412

  日期：2019.10.30

  4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) is an important target site for discovering new bleaching herbicides. To explore novel HPPD inhibitors with excellent herbicidal activity, a series of novel N-aroyl diketone/triketone derivatives were rationally designed by splicing active groups and bioisosterism. Bioassays revealed that most of these derivatives displayed preferable herbicidal

  4-羟基苯基丙酮酸双加氧酶（HPPD，EC 1.13.11.27）是发现新的漂白除草剂的重要靶位。为了探索具有优异除草活性的新型HPPD抑制剂，通过拼接活性基团和生物等排异构体，合理设计了一系列新型N-芳酰基二酮/三酮衍生物。生物测定法显示，这些衍生物大多数对0.045 mmol / m2的菜E（EC）和0.090 mmol / m2的芥菜（AJ）表现出较好的除草活性。特别地，与商业化的化合物甲基磺草酮相比，化合物If具有更强的效力。分子对接表明目标化合物和甲基磺草酮的相应活性分子与周围残基共享相似的相互作用，从而导致与拟南芥HPPD活性位点的完美相互作用。
• Isoxazole carboxamide derivatives as ghrelin receptor modulators
  申请人：Liu Gang

  公开号：US20060089398A1

  公开（公告）日：2006-04-27

  The present invention is related to compounds of formula (I), or a therapeutically suitable salt or prodrug thereof, the preparation of the compounds, compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by ghrelin including anorexia, cancer cachexia, eating disorders, age-related decline in body composition, weight gain, obesity, and diabetes mellitus.

  本发明涉及式(I)的化合物，或其在治疗上适用的盐或前药，该化合物的制备，含有该化合物的组合物以及在预防或治疗由胃饥素调节的疾病中使用该化合物，包括厌食症、癌症恶病质、进食障碍、与年龄相关的身体组成下降、体重增加、肥胖和糖尿病。
• Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof
  作者：Eduardo de Pedro Beato、Daniele Mazzarella、Matteo Balletti、Paolo Melchiorre

  DOI：10.1039/d0sc02313b

  日期：——

  detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue

  我们详细介绍了一种策略，该策略使用相应的氯化物和酸酐通过激活后，使用市售的亲核有机催化剂来生成酰基和氨基甲酰基基团。亲核酰基取代路径。然后，在Giese型加成过程中，所得的亲核基团被各种贫电子烯烃截获。化学过程需要低能光子（蓝色LED）来激活酰基和氨基甲酰基自由基前体，由于它们的高还原电位，因此不容易基于氧化还原的激活机制。为了阐明这种催化光化学自由基产生策略的关键机理，我们结合了瞬态吸收光谱研究，电化学研究，量子产率测量和关键中间体的表征。我们确定了各种非循环中间体，它们与反应性自由基进行光调节平衡。

表征谱图