2-氯甲基-5-(4-甲基苯基)-1,3,4-恶二唑 | 287197-95-9

• 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-氯甲基-5-(4-甲基苯基)-1,3,4-恶二唑
• 中文别名: 2-氯甲基-5-(4-甲苯基)-1,3,4-二唑
• 英文名称: 2-(chloromethyl)-5-(p-tolyl)-1,3,4-oxadiazole
• 英文别名: 2-(Chloromethyl)-5-(4-methylphenyl)-1,3,4-oxadiazole
• CAS: 287197-95-9
• 化学式: C₁₀H₉ClN₂O
• mdl: MFCD00662318
• 分子量: 208.647
• InChiKey: JDAULQMOFMANSL-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 海关编码：
  2934999090
• 危险品运输编号：
  3261

SDS

Name:	2-(Chloromethyl)-5-(4-methylphenyl)-1 3 4-oxadiazole 95+% Material Safety Data Sheet
Synonym:
CAS:	287197-95-9

Section 1 - Chemical Product MSDS Name:2-(Chloromethyl)-5-(4-methylphenyl)-1 3 4-oxadiazole 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
287197-95-9	2-(Chloromethyl)-5-(4-methylphenyl)-1,	95+%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
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.

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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# 287197-95-9: 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
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 117 - 119 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: C10H9ClN2O
Molecular Weight: 209

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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, hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide, ammonia.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 287197-95-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(Chloromethyl)-5-(4-methylphenyl)-1,3,4-oxadiazole - 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# 287197-95-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 287197-95-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 287197-95-9 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：

  2-氯甲基-5-(4-甲基苯基)-1,3,4-恶二唑 在 硫脲 作用下， 以 四氢呋喃 为溶剂， 生成 2-(chloromethyl)-5-(p-tolyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  5-{[双（唑基甲硫基）]亚甲基}嘧啶-2,4,6-（1H、3H、5H）-三酮的一锅法合成

  摘要：

  一类迄今为止未知的三杂环，双恶二唑基/双噻二唑基嘧啶三酮/硫代嘧啶二酮通过一锅反应制备，并研究了它们的抗菌活性。

  DOI：

  10.1002/ardp.201000085
• 作为产物：
  描述：

  对甲基苯甲酸乙酯 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2-氯甲基-5-(4-甲基苯基)-1,3,4-恶二唑
  参考文献：
  名称：

  设计和合成新的诺氟沙星-1,3,4-恶二唑杂种作为对耐甲氧西林的金黄色葡萄球菌（MRSA）的抗菌剂。

  摘要：

  为了寻找新的抗菌药物来控制耐甲氧西林的金黄色葡萄球菌（MRSA），设计并合成了一类新的诺氟沙星-1,3,4-恶二唑杂种。评估了对药物敏感细菌金黄色葡萄球菌和MRSA临床耐药菌株的抗菌活性。化合物5k对金黄色葡萄球菌（MIC：2μg/ mL）和MRSA1-3（MIC：0.25-1μg/ mL）表现出优异的抗菌活性。时间杀灭动力学表明，化合物5k在杀死金黄色葡萄球菌和MRSA方面优于常用抗生素万古霉素。而且，化合物5k可以在短时间内抑制细菌并破坏其膜，并且对NRK-52E细胞显示出非常低的细胞毒性。还讨论了一些有趣的结构-活性关系（SAR）。这些结果表明这些诺氟沙星1,3，

  DOI：

  10.1016/j.ejps.2019.104966

文献信息

• [EN] SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS<br/>[FR] COMPOSÉS TÉTRAHYDROISOQUINOLINES SUBSTITUÉS EN TANT QU'INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013055984A1

  公开（公告）日：2013-04-18

  The present invention provides compounds of Formula (I): or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.

  本发明提供了化合物的公式(I)：或其立体异构体，以及其药学上可接受的盐，其中所有变量如本文所定义。这些化合物是XIa因子和/或血浆激肽酶的抑制剂，可用作药物。
• Design, synthesis and anticancer activity of new monastrol analogues bearing 1,3,4-oxadiazole moiety
  作者：Fatma A.F. Ragab、Sahar M. Abou-Seri、Salah A. Abdel-Aziz、Abdallah M. Alfayomy、Mohamed Aboelmagd

  DOI：10.1016/j.ejmech.2017.06.026

  日期：2017.9

  A series of dihydropyrimidine (DHPM) derivatives bearing 1,3,4-oxadiazole moiety was designed and synthesized as monastrol analogues. The new compounds were screened for their cytotoxic activity toward 60 cancer cell lines according to NCI (USA) protocol. Seven compounds were further examined against the most sensitive cell lines, leukemia HL-60(TB) and MOLT-4. The most active compounds were 9m against

  设计并合成了一系列带有1,3,4-恶二唑部分的二氢嘧啶（DHPM）衍生物，作为monastrol类似物。根据NCI（USA）方案，筛选了这些新化合物对60种癌细胞系的细胞毒活性。进一步针对最敏感的细胞系白血病HL-60（TB）和MOLT-4检测了7种化合物。活性最高的化合物对HL-60（TB）的 抗性为9m（IC 50  = 56 nM），对MOLT-4的活性为9n（IC 50 = 80 nM），比蒙那那尔更强（分别为IC 50  = 147和215 nM）。9m处理的HL-60（TB）细胞和9n处理的MOLT-4细胞的细胞周期分析 如膜联蛋白V-FITC染色所显示的，显示出在G2 / M期的细胞周期停滞和促凋亡活性。
• Alpha-helical mimetics
  申请人：Lessene Guillaume Laurent

  公开号：US20080153802A1

  公开（公告）日：2008-06-26

  Benzoyl urea derivatives that are alpha helical peptides mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting-moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralizing pro-survival Bcl-2 proteins. Use of benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also described.

  公开了模拟α螺旋肽的苯甲酰脲衍生物，这些衍生物模拟BH3-仅蛋白，含有它们的组合物，它们与细胞靶向基团的结合，以及它们在调节细胞死亡中的用途。苯甲酰脲衍生物能够结合并中和促生存的Bcl-2蛋白。还描述了在治疗和/或预防与细胞死亡失调相关的疾病或症状中使用苯甲酰脲衍生物。
• Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4-thiadiazolyl)methylthio)methylene)malononitriles
  作者：V. Padmavathi、G. Dinneswara Reddy、S. Nagi Reddy、K. Mahesh

  DOI：10.1016/j.ejmech.2011.01.063

  日期：2011.4

  The reactivity of ketene dithiolates in the presence of different equivalents of sodium ethoxide was studied. 2-(Bis((5-aryl-1,3,4-oxadiazol-2-yl)methylthio)methylene)malononitriles 5 and 2-(bis((5-aryl-1,3,4-thiadiazol-2-yl)methylthio)methylene)malononitriles 6 were prepared by the reaction of malononitrile with carbon disulfide and 5-aryl-2-(chloromethyl)-1,3,4-oxadiazoles 3/5-aryl-2-(chloromethyl)-1

  研究了在不同当量乙醇钠存在下乙烯酮二硫醇盐的反应性。2-（双（（（5-芳基-1,3,4-恶二唑-2-基）甲硫基）亚甲基）丙二腈5和2-（双（（5-芳基-1,3,4-噻二唑-2-基通过丙二腈与二硫化碳和5-芳基-2-（氯甲基）-1,3,4-恶二唑3 / 5-芳基-2-（氯甲基）-1,3的反应制备）甲硫基）亚甲基）丙二腈6，4-噻二唑4。测定了先导化合物的初步抗微生物和抗氧化活性。
• Design and synthesis of pyrimidine-5-carbonitrile hybrids as COX-2 inhibitors: Anti-inflammatory activity, ulcerogenic liability, histopathological and docking studies
  作者：Abdallah M. Alfayomy、Salah A. Abdel-Aziz、Adel A. Marzouk、Montaser Sh. A. Shaykoon、Atsushi Narumi、Hiroyuki Konno、Sahar M. Abou-Seri、Fatma A.F. Ragab

  DOI：10.1016/j.bioorg.2020.104555

  日期：2021.3

  Two new series of 1,3,4-oxadiazole and coumarin derivatives based on pyrimidine-5-carbonitrile scaffold have been synthesized and evaluated for their COX-1/COX-2 inhibitory activity. Compounds 10c, 10e, 10h-j, 14e-f, 14i and 16 were found to be the most potent and selective inhibitors of COX-2 (IC50 0.041-0.081 μM, SI 139.74-321.95). Eight compounds were further investigated for their in vivo anti-inflammatory

  合成了两个新系列的基于 pyrimidine-5-carbonitrile 支架的 1,3,4-恶二唑和香豆素衍生物，并评估了它们的 COX-1/COX-2 抑制活性。发现化合物10c、10e、10h-j、14e-f、14i和16是最有效和选择性的 COX-2 抑制剂（IC 50 0.041-0.081 μM，SI 139.74-321.95）。进一步研究了八种化合物的体内抗炎活性。最活跃的衍生物10c , 10j和14e显示出优于参考药物塞来昔布的体内抗炎活性（水肿抑制百分比 39.3-48.3，1 小时；58.4-60.5，2 小时；70.8-83.2，3 小时；78.9-89.5，4 小时）（水肿抑制百分比 38.0） ，1 小时；48.8、2 小时；58.4、3 小时；65.4、4 小时）。还测试了这些衍生物的致溃疡倾向，化合物10j与塞来昔布相比表现出更好的安全性，而10c和14e表现出轻度损伤。COX-2