2-巯基-5-甲基苯并恶唑 | 22876-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 2-巯基-5-甲基苯并恶唑
• 中文别名: 5-甲基苯并噁唑啉；5-甲基苯并唑啉；5-甲基苯并恶唑啉；2-巯基-6-甲基苯并恶唑；5-甲基-2,3-二氢-1,3-苯并恶唑-2-硫酮
• 英文名称: 5-methylbenzo[d]oxazole-2-thiol
• 英文别名: 2-mercapto-5-methylbenzoxazole；5-methyl-benzooxazole-2-thiol；5-methyl-3H-1,3-benzoxazole-2-thione
• CAS: 22876-22-8
• 化学式: C₈H₇NOS
• mdl: MFCD00052492
• 分子量: 165.216
• InChiKey: SSWZUOXLFTXIEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  223-225°C
• 沸点：
  260.9±33.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。应避免接触氧化物和空气。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  在干性保护气体中处理，保持贮藏容器密封，并将其存放在阴凉、干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methyl-1,3-benzoxazole-2-thiol
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Methyl-1,3-benzoxazole-2-thiol
CAS number: 22876-22-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H7NOS
Molecular weight: 165.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法

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用途

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反应信息

• 作为反应物：
  描述：

  2-巯基-5-甲基苯并恶唑 在 sodium hydroxide 、 五氯化磷 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 3.0h， 生成 N-[2-cyanoethyl-(5-methyl-1,3-benzoxazol-2-yl)amino]formamide
  参考文献：
  名称：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation

  摘要：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.

  DOI：

  10.1021/jm00117a010
• 作为产物：
  描述：

  5-甲基苯并唑 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 1,10-菲罗啉 、 copper dichloride 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以64%的产率得到2-巯基-5-甲基苯并恶唑
  参考文献：
  名称：

  铜催化电子缺陷芳烃的CH键硫代反应中的元素硫作为硫化剂

  摘要：

  通过利用元素硫作为硫醇化剂和氧化剂，对缺电子的芳烃进行了铜催化的直接CH键硫醇化反应。各种缺乏电子的芳烃被证明适用于这种转变。初步的机理研究表明，该反应经历了一个自由基途径，其中三硫自由基阴离子（S3•-）可能起着至关重要的作用。同时，KIE实验表明，CH键断裂不参与速率确定步骤。

  DOI：

  10.1039/c7ob02036h

文献信息

• ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND METHOD OF USING THEREOF
  申请人：Meng Charles Q.

  公开号：US20140142114A1

  公开（公告）日：2014-05-22

  The present invention relates to novel anthelmintic compounds of formula (I) below: wherein Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.

  本发明涉及以下式（I）的新型驱虫化合物： 其中 Y和Z分别是双环碳环或双环杂环基团，或者Y或Z中的一个是双环碳环或双环杂环基团，另一个是烷基，烯基，炔基，环烷基，苯基，杂环基或杂芳基，以及变量X 1 ，X 2 ，X 3 ，X 4 ，X 5 ，X 6 ，X 7 和X 8 如本文所定义。本发明还提供了包含本发明的驱虫化合物的兽药组合物，以及它们用于治疗和预防动物寄生虫感染的用途。
• Synthesis and anticancer activity evaluation of N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives containing (benz)azole moiety
  作者：Leyla Yurttaş、Yusuf Özkay、Gülşen Akalın-Çiftçi、Şafak Ulusoylar-Yıldırım

  DOI：10.3109/14756366.2013.763253

  日期：2014.4.1

  investigate their anticancer activity. The structure of the compounds was confirmed by IR, (1)H-NMR, and MS spectral data and elemental analyses. Anticancer effect of the compounds was evaluated against A549 and C6 tumor cell lines. MTT, analysis of DNA synthesis, acridine orange/ethidium bromide staining method and analysis of caspase-3 activation assays were performed for anticancer activity investigations

  合成了一类新型的新型噻唑-（苯并）唑衍生物以研究其抗癌活性。化合物的结构通过IR，（1）H-NMR和MS光谱数据以及元素分析确认。评价了化合物对A549和C6肿瘤细胞系的抗癌作用。进行了MTT，DNA合成分析，a啶橙/溴化乙锭染色方法和caspase-3活化分析，以进行抗癌活性研究。带有5-氯和5-甲基苯并咪唑基的化合物6f和6g显示出显着的抗癌活性。还观察到这些化合物将肿瘤细胞引导至凋亡途径的潜力，这是抗癌作用的前提。
• Benzoxazolamines and Benzothiazolamines: Potent, Enantioselective Inhibitors of Leukotriene Biosynthesis with a Novel Mechanism of Action
  作者：Edward S. Lazer、Clara K. Miao、Hin-Chor Wong、Ronald Sorcek、Denice M. Spero、Alex Gilman、Kollol Pal、Mark Behnke、Anne G. Graham

  DOI：10.1021/jm00033a008

  日期：1994.4

  phenylalanine with a cyclohexyl group greatly enhance potency. Several ester bioisosteres that retain potency and enantiomeric selectivity are described. Lead optimization culminated in (S)-N-[2-cyclohexyl-1-(2-pyridinyl)ethyl]-5-methyl-2-benzoxazolamine+ ++ (43b), IC50 0.001 microM. The compounds described are not inhibitors of 5-lipoxygenase but, rather, act at the level of arachidonic acid release.

  描述了一系列抑制白三烯（LT）生物合成的苯并恶唑胺和苯并噻唑胺类似物。最初的铅（S）-N-（苯并噻唑-2-基）苯丙氨酸乙酯（5a）在筛选程序中被发现，该程序可抑制Ca-离子载体-A23187诱导的人多形核白细胞释放LTB4（IC50 0.23 microM ）。通过结构修饰，确定了5-位上的疏水取代基以及苯丙氨酸的苯环被环己基取代极大地增强了效能。描述了几种保留效力和对映异构体选择性的酯类生物甾体。铅优化最终达到（S）-N- [2-环己基-1-（2-吡啶基）乙基] -5-甲基-2-苯并恶唑胺+ ++（43b），IC50 0.001 microM。所述化合物不是5-脂氧合酶的抑制剂，而是
• Analgesic Compounds, Compositions, and Uses Thereof
  申请人：Mannion James C.

  公开号：US20110224269A1

  公开（公告）日：2011-09-15

  The invention relates to compounds, compositions, and methods for diminishing pain in a subject in need thereof comprising administering the compounds and compositions herein described.

  这项发明涉及化合物、组合物和方法，用于减轻需要的受试者的疼痛，包括给予所述的化合物和组合物。
• Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media
  作者：Zhi-Bing Dong、Jin-Quan Chen、Jia Guo

  DOI：10.1055/s-0039-1690854

  日期：2020.7

  A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o-aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C–S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also

  描述了一种用于合成2-烷基硫代苯并唑的高效三组分方案。四甲基秋兰姆二硫化物（TMTD）与邻氨基硫酚进行环化，生成中间体2-巯基苯并噻唑，并与卤代烷烃连续进行C-S偶联，从而在一个一锅过程中平稳地获得了一系列2-烷基取代的硫代苯并噻唑。该方法也可用于制备2-烷基取代的硫代苯并恶唑和2-烷基取代的硫代苯并咪唑。廉价且容易获得的原料，无金属催化剂，广泛的底物范围以及以水为溶剂是该协议的特点。