苯基-3-(2-噻唑基)-2-硫脲 | 14901-16-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硫脲
• 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: 苯基-3-(2-噻唑基)-2-硫脲
• 中文别名: 1-苯基-3-(2-噻唑基)-2-硫脲
• 英文名称: 1-phenyl-3-(thiazol-2-yl)thiourea
• 英文别名: 1-phenyl-3-(1,3-thiazol-2-yl)thiourea；1-phenyl-3-(2-thiazolyl)-2-thiourea；1-phenyl-3-(thiazole-2-yl)thiourea；N-phenyl-N'-(2-thiazolyl) thiourea；N-phenyl-N'-(thiazol-2-yl)thiourea；1-phenyl-3-(thiazolyl)-2-thiourea
• CAS: 14901-16-7
• 化学式: C₁₀H₉N₃S₂
• mdl: MFCD00005321
• 分子量: 235.334
• InChiKey: GCZZOZBWAZHCAN-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C (dec.)(lit.)
• 密度：
  1.3479 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S39
• 危险类别码：
  R22,R41,R37/38
• WGK Germany：
  3
• RTECS号：
  YU1398000
• 海关编码：
  2934100090

SDS

Name:	1-Phenyl-3-(2-Thiazolyl)-2-Thiourea 97+% Material Safety Data Sheet
Synonym:	Thiourea, N-Phenyl-N'-2-Thiazolyl-
CAS:	14901-16-7

Section 1 - Chemical Product MSDS Name:1-Phenyl-3-(2-Thiazolyl)-2-Thiourea 97+% Material Safety Data Sheet
Synonym:Thiourea, N-Phenyl-N'-2-Thiazolyl-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14901-16-7	1-Phenyl-3-(2-Thiazolyl)-2-Thiourea	97+	238-970-4

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 14901-16-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Powder
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 183.00 - 185.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H9N3S2
Molecular Weight: 235.32

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14901-16-7: YU1398000 LD50/LC50:
Not available.
Carcinogenicity:
1-Phenyl-3-(2-Thiazolyl)-2-Thiourea - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 14901-16-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14901-16-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14901-16-7 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：

  苯基-3-(2-噻唑基)-2-硫脲 在 potassium carbonate 作用下， 以 异丙醇 、 丙酮 为溶剂， 生成 N-phenyl-N'-(thiazol-2-yl)cyanoguanidine
  参考文献：
  名称：

  微波辅助合成N，N'-二芳基氰基胍。

  摘要：

  [反应：见正文]描述了在微波辅助条件下从其相应的硫脲合成N，N'-二芳基氰基胍的温和，高效且高产方法。合成了一系列同时具有给电子和吸电子取代基的氰基胍。通过使用极性溶剂以及适度的温度来促进反应。

  DOI：

  10.1021/ol050728q
• 作为产物：
  描述：

  生成 四氰基乙烯 、 苯基-3-(2-噻唑基)-2-硫脲
  参考文献：
  名称：

  Mohamed; Hassan; Ibrahim, Pharmazie, 1992, vol. 47, # 8, p. 592 - 595

  摘要：

  DOI：

文献信息

• Efficient construction of C–C bonds from aryl halides/aryl esters with arylboronic acids catalysed by palladium(II) thiourea complexes
  作者：Manikandan Thimma Sambamoorthy、Ramesh Rengan、Malecki Jan Grzegorz

  DOI：10.1002/aoc.5181

  日期：2019.11

  Interestingly, the palladium(II) thiourea complexes showed the highest catalytic activity with 0.1 mol% catalyst loading in Suzuki–Miyaura cross‐coupling reactions utilizing a range of aryl bromides/unactivated aryl chlorides with arylboronic acids as coupling partners in aqueous–organic media. Syntheses of diaryl ketones using aryl esters and arylboronic acids as coupling partners were also achieved with low

  已成功地合成了一组新的包含苯基（噻唑基）硫脲配体的钯（II）配合物，并借助分析和光谱（IR，UV-可见光和NMR）方法对其进行了表征。单晶X射线衍射法证实了新钯配合物中硫脲配体的N ^ S配位模式具有N ^ S配位模式的扭曲方平面几何结构。有趣的是，钯（II）硫脲配合物在铃木-宫浦交叉偶联反应中显示出最高的催化活性，催化剂负载量为0.1摩尔％，利用一系列芳基溴化物/未活化的芳基氯化物与芳基硼酸作为水性有机介质中的偶合伙伴。使用芳基酯和芳基硼酸作为偶合伙伴合成二芳基酮也可以在20小时内以较低的催化剂负载量实现。我们的催化剂的潜力通过其广泛的底物范围，低的催化剂负载量和高的分离产率得到了证明。此外，还研究了关键参数如溶剂，碱，温度和催化剂用量的影响。
• Novel Thiazole Derivatives of Medicinal Potential: Synthesis and Modeling
  作者：Nour E. A. Abdel-Sattar、Abeer M. El-Naggar、M. S. A. Abdel-Mottaleb

  DOI：10.1155/2017/4102796

  日期：——

  This paper reports on the synthesis of new thiazole derivatives that could be profitably exploited in medical treatment of tumors. Molecular electronic structures have been modeled within density function theory (DFT) framework. Reactivity indices obtained from the frontier orbital energies as well as electrostatic potential energy maps are discussed and correlated with the molecular structure. X-ray

  本文报道了可用于肿瘤医学治疗的新型噻唑衍生物的合成。分子电子结构已在密度函数理论 (DFT) 框架内建模。讨论了从前沿轨道能量以及静电势能图获得的反应性指数，并将其与分子结构相关联。一种新化合物的 X 射线晶体学数据被测量并用于支持和验证理论结果。
• Nickel(II)‐Catalyzed Selective <i>(E)</i> ‐Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction
  作者：Gunasekaran Balamurugan、Rengan Ramesh

  DOI：10.1002/cctc.202101455

  日期：2022.1.21

  characterized with FT-IR, NMR, HRMS and single crystal X-ray method. The new complexes were tuned as effective homogeneous catalysts for synthesis of selective (E)-olefins from the reaction of methyl heteroarenes and benzyl alcohols via greener ADC methodology. The earth abundant nickel complexes performed well with 4 mol% of catalyst loading at 110 °C for 35 h, resulting in good to excellent yields (40–93 %)

  脱氢偶联：合成了两种Ni(II)硫脲配合物，并用FT-IR、NMR、HRMS和单晶X射线法对其进行了结构表征。新的配合物被调整为有效的均相催化剂，用于通过更环保的 ADC 方法从甲基杂芳烃和苯甲醇的反应中合成选择性(E) -烯烃。地球丰富的镍络合物在 4 mol% 的催化剂负载下在 110 °C 下 35 小时表现良好，产生了良好的产率 (40–93%)。
• Antimicrobial and Anti-biofilm Activity of Thiourea Derivatives Incorporating a 2-Aminothiazole Scaffold
  作者：Joanna Stefanska、Grażyna Nowicka、Marta Struga、Daniel Szulczyk、Anna Eugenia Koziol、Ewa Augustynowicz-Kopec、Agnieszka Napiorkowska、Anna Bielenica、Wojciech Filipowski、Anna Filipowska、Aleksandra Drzewiecka、Gabriele Giliberti、Silvia Madeddu、Stefano Boi、Paolo La Colla、Giuseppina Sanna

  DOI：10.1248/cpb.c14-00837

  日期：——

  A series of new thiourea derivatives of 1,3-thiazole have been synthesized. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. Compounds were also tested for their in vitro tuberculostatic activity against the Mycobacterium tuberculosis H37Rv strain, as well as two ‘wild’ strains isolated from tuberculosis patients. Compounds 3 and 9 showed significant inhibition against Gram-positive cocci (standard strains and hospital strain). The range of MIC values is 2–32 µg/mL. Products 3 and 9 effectively inhibited the biofilm formation of both methicillin-resistant and standard strains of S. epidermidis. The halogen atom, especially at the 3rd position of the phenyl group, is significantly important for this antimicrobial activity. Moreover, all obtained compounds resulted in cytotoxicity and antiviral activity on a large set of DNA and RNA viruses, including Human Immunodeficiency Virus type 1 (HIV-1) and other several important human pathogens. Compound 4 showed activity against HIV-1 and Coxsackievirus type B5. Seven compounds resulted in cytotoxicity against MT-4 cells (CC50<10 µM).

  我们合成了一系列新的 1,3-噻唑硫脲衍生物。对所有获得的化合物都进行了抗多种微生物（包括革兰氏阳性球菌、革兰氏阴性杆菌和白色念珠菌）的体外测试。此外，还测试了化合物对结核分枝杆菌 H37Rv 菌株以及从结核病患者体内分离出的两种 "野生 "菌株的体外抗结核活性。化合物 3 和 9 对革兰氏阳性球菌（标准菌株和医院菌株）有明显的抑制作用。MIC 值范围为 2-32 µg/mL。产品 3 和 9 能有效抑制耐甲氧西林表皮葡萄球菌和标准菌株的生物膜形成。卤素原子，尤其是位于苯基第 3 位的卤素原子，对这种抗菌活性非常重要。此外，所有获得的化合物都对大量 DNA 和 RNA 病毒具有细胞毒性和抗病毒活性，包括人类免疫缺陷病毒 1 型（HIV-1）和其他几种重要的人类病原体。化合物 4 对 HIV-1 和 B5 型柯萨奇病毒具有活性。7 种化合物对 MT-4 细胞具有细胞毒性（CC50<10 µM）。
• One-pot synthesis of thiazolo[3,4-a]quinoxalines and the related heterocyclic systems using 4-hydroxy-4-alkoxycarbonyl-3,5-diaryl-2-aryliminothia(selena)zolidines as versatile reagents
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Alsu A. Balandina、Sergey V. Kharlamov、Tat'yana N. Beschastnova、Il'dar Kh. Rizvanov、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.06.084

  日期：2012.9

  An efficient and versatile one-step method for the synthesis of thiazolo[3,4-a]quinoxalines and related new heterocyclic systems have been developed on the basis of a new strategy for the construction of the pyrazine ring system. The key step of the process involves the cascade annulation of the iminothiazolopyrazine system to benzene in the reaction of 4-hydroxy-3,5-diaryl-2-phenyliminothiazolidines

  在构建吡嗪环系统的新策略的基础上，开发了一种高效且通用的一步法合成噻唑并[3,4- a ]喹喔啉和相关的新杂环系统。该方法的关键步骤涉及在4-羟基-3,5-二芳基-2-苯基亚甲基噻唑烷与1,2-二氨基苯的反应中，亚氨基咪唑并吡嗪系统级联成苯。在该反应中使用硒类似物代替噻唑烷衍生物，会导致硒代氮杂[3,4- a ]喹喔啉，而用氮杂类似物代替1,2-二氨基苯得到噻唑并[3,4- a ]喹喔啉的氮杂类似物。。

表征谱图