2-(2-噻吩亚甲基)肼-1-硫代甲酰胺 | 5351-91-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(2-噻吩亚甲基)肼-1-硫代甲酰胺
• 英文名称: thiophene-2-carbaldehyde thiosemicarbazone
• 英文别名: thiophene-2-carboxaldehyde thiosemicarbazone；2-(thiophen-2-ylmethylene)hydrazinecarbothioamide；1-((thiophen-2-yl)methylene)thiosemicarbazide；N'-(thiophen-2-ylmethylideneamino)carbamimidothioic acid
• CAS: 5351-91-7
• 化学式: C₆H₇N₃S₂
• mdl: MFCD23698441
• 分子量: 185.274
• InChiKey: YNTKURSKMLATKI-UHFFFAOYSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  329.5±34.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 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,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2934999090

SDS

Name:	2-(2-Thienylmethylidene)hydrazine-1-carbothioamide 97% Material Safety Data Sheet
Synonym:	1-(2-Thienyl)thiosemicarbazid
CAS:	5351-91-7

Section 1 - Chemical Product MSDS Name:2-(2-Thienylmethylidene)hydrazine-1-carbothioamide 97% Material Safety Data Sheet
Synonym:1-(2-Thienyl)thiosemicarbazid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5351-91-7	2-(2-Thienylmethylidene)hydrazine-1-ca	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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# 5351-91-7: 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: Liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 182 - 185 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: C6H7N3S2
Molecular Weight: 185

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, acids, reducing agents, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5351-91-7: XM8180000 LD50/LC50:
CAS# 5351-91-7: Oral, mouse: LD50 = 226 mg/kg.
Carcinogenicity:
2-(2-Thienylmethylidene)hydrazine-1-carbothioamide - 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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 5351-91-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5351-91-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5351-91-7 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：

  2-(2-噻吩亚甲基)肼-1-硫代甲酰胺 在 iron(III) chloride 作用下， 以 水 为溶剂， 生成 5-(2-噻吩基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  Cu(II) and Fe(III) Catalyzed Synthesis of Novel Thiophene Hybridized Thiadiazolyl Schiff Bases (TTS) as COX-2 Selective Inhibitor

  摘要：

  设计并合成了一系列新型噻吩杂化噻二唑基希夫碱 (TTS) 在硝酸铜（CuII）催化下合成希夫碱，随后在氯化铁（FeIII）催化下环化成噻二唑。 (FeIII) 催化环化成噻二唑。这些分子的设计灵感来自于 噻二唑、希夫碱和噻吩的抗炎特性。根据 质谱、红外光谱、1H 和 13C NMR 测量的信息，确定了最近合成的化合物的结构。 确定了最近合成的化合物的结构。进行分子对接的目的是为了更好地了解 候选药物与 COX-1（PDB ID：3KK6）和 COX-2（PDB ID：3Q7D）炎症相关靶点之间的相互作用。 炎症相关靶点之间的相互作用。化合物 3a-f 显示出与 COX-2 更稳定的结合复合物 (相比（-4.86 至 -5.94 kcal/mol），化合物 3a-f 与 COX-2 的结合复合物更为稳定（-8.09 至 -9.13 kcal/mol）。此外，在 在体内分析中，化合物 3a 与参考药物双氯芬酸相比，表现出卓越的抗炎活性。 有趣的是，利用 qRT-PCR 进行的 mRNA 表达分析表明，与 COX-2 相比，化合物 3a 对 COX-2 有特异性抑制作用。 与 COX-1 相比，COX-2 的 mRNA 表达得到了抑制，这进一步证实了之前的研究结果。总之，这些发现 为这些化合物作为新型先导分子开发提供了机会。 非甾体抗炎药的替代品。

  DOI：

  10.14233/ajchem.2023.27745
• 作为产物：
  描述：

  2-噻吩甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 生成 2-(2-噻吩亚甲基)肼-1-硫代甲酰胺
  参考文献：
  名称：

  新型噻唑-苯并咪唑类作为EGFR抑制剂的设计，合成，生物学评估，QSAR分析和分子建模。

  摘要：

  杂环如噻唑和苯并咪唑被认为是特权结构，因为它们构成了几种FDA批准的用于癌症治疗的药物。在这项工作中，设计了一组新的2-（2-（取代）肼基）-4-（1-甲基-1 H-苯并[ d ]咪唑-2-基）噻唑4a-q作为表皮生长因子受体（EGFR）抑制剂，并使用简明的合成方法合成。已经在体外评估了新的目标化合物对EGFR TK的抑制活性。化合物4n，4h，4i，4a和4d与作为参考药物的厄洛替尼相比，具有显着的效力（IC50，71.67–152.59 nM； IC50厄洛替尼，152.59 nM）。此外，MTT分析表明，化合物4j，4a，4f，4h，4n对人乳腺癌细胞系（MCF-7）产生了最有希望的细胞毒性作用（IC50； 5.96-11-1.91 µM；厄洛替尼IC50； 4.15 µM）。化合物4a作为EGFR TK抑制剂和抗乳腺癌药物显示出有希望的活性。此外，4a诱导凋亡作用，并在G2 / M

  DOI：

  10.1016/j.bmc.2020.115657

文献信息

• An Efficient Synthesis of Some New Hydrazone Derivatives Containing 1,2,3-Triazole and Thiazole
  作者：Keyume Ablajan、Wang Liju、Anagu Tuoheti

  DOI：10.2174/157017861010131126115715

  日期：2013.11

  The syntheses of hydrazone derivatives with thiazole and triazole rings were described. The target compounds 7a-j and 8a-g with the hydrazine based structure containing thiazole and triazole rings were synthesized respectively through the reactions of α-bromomethylpyrazole ketone 3 with arylethanone thiosemicarbazones 5a-j and the reactions of pyrazol thiosemicarbazone 4 with α-bromomethyl aryl ketones

  描述了derivatives衍生物与噻唑和三唑环的合成。分别通过αα-溴甲基吡唑酮3与芳酮硫代半氨基咔唑酮5a-j的反应和吡唑硫代半碳a酮4与α-β的反应，分别合成具有噻唑和三唑环的肼基结构的目标化合物7a-j和8a-g。在没有催化剂的回流条件下，溴甲基芳基酮6a-g。此外，使用一锅法开发了一种生态友好的合成化合物8a-g的简便方法。通过使用H 2 O 2诱导的具有氧化损伤的PC 12细胞，测试了目标化合物的初步生物活性。
• 2-Bromo-1-(1<i>H</i>-pyrazol-4-yl)ethanone: Versatile Precursor for Novel Mono- and Bis[pyrazolylthiazoles]
  作者：Mostafa E. Salem、Ahmed F. Darweesh、Ahmed E. M. Mekky、Ahmad M. Farag、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.2571

  日期：2017.1

  The synthesis of novel bis(thiazoles) 20a, 20b, 20c and 23a, 23b, 23c is reported. Thus, reaction of 2‐bromo‐1‐(5‐methyl‐1‐phenyl‐1H‐pyrazol‐4‐yl)ethanone (6) with the corresponding thioamide derivatives 7a,7b, in refluxing EtOH in the presence of triethylamine, afforded 4‐pyrazolylthiazoles 8a, 8b in good yields. On the other hand, the novel bis(thiazoles) 20a, 20b, 20c and 23a, 23b, 23c were obtained

  报道了新型双（噻唑）20a，20b，20c和23a，23b，23c的合成。因此，在三乙胺存在下，在回流的EtOH中，2-溴-1-（5-甲基-1-苯基-1 H-吡唑-4-基）乙酮（6）与相应的硫酰胺衍生物7a，7b反应，得到了4-吡唑基噻唑8a和8b，收率很高。另一方面，新型双（噻唑）20a，20b，20c和23a，23b，23c由6与相应的苯甲醛硫代半金属咔唑19a，19b，19c，22a，22b，22c在回流的EtOH中的反应获得。通过将相应的双（醛）18a，18b，18c和21a，21b，21c与硫代氨基脲缩合获得化合物19a，19b，19c和22a，22b，22c。
• Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
  作者：Simone Carradori、Dante Rotili、Celeste De Monte、Alessia Lenoci、Melissa D'Ascenzio、Veronica Rodriguez、Patrizia Filetici、Marco Miceli、Angela Nebbioso、Lucia Altucci、Daniela Secci、Antonello Mai

  DOI：10.1016/j.ejmech.2014.04.042

  日期：2014.6

  thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis

  最近，我们描述了一些（噻唑-2-基）azo作为抗原生动物，抗真菌和抗MAO试剂以及Gcn5 HAT抑制剂。在这些最后的化合物中，CPTH2和CPTH6在细胞中显示出HAT抑制作用和广泛的抗癌特性。为了鉴定比两个原型更有效的HAT抑制剂，我们合成了几种新的（噻唑-2-基）azo酮，包括一些相关的噻唑烷和嘧啶4（3 H）-酮，并测试了我们现有的整个文库针对人p300和PCAF HAT酶的实验室。某些化合物（1x，1c '，1d '，1i '和2m）在抑制p300 HAT酶方面比CPTH2和CPTH6更有效。在人白血病U937和结肠癌HCT116细胞（100μM，30小时）中进行测试时，1x，1i '和2m产生的凋亡（U937细胞）或类似细胞（HCT116细胞）高于CPTH6，并且在诱导细胞分化方面比CPTH6更有效（U937细胞）。
• Synthesis and Antimicrobial Evaluation of Some New 4,5′-Bisthiazoles
  作者：Tibor Rozsa、Mihaela Duma、Laurian Vlase、Ioana Ionuţ、Adrian Pîrnău、Brînduşa Tiperciuc、Ovidiu Oniga

  DOI：10.1002/jhet.2054

  日期：2015.7

  bisthiazole derivatives represent a prevalent scaffold in the antimicrobial drug discovery. Therefore, we have decided to synthesize some new series of 4,5′‐bisthiazoles. A total of 17 compounds were synthesized, their structural elucidation being based on elemental analysis (C,H,N,S) and spectroscopic data (MS and 1H NMR). Their in vitro antimicrobial activities were assessed against several Gram‐positive

  噻唑和联噻唑衍生物代表了抗菌药物发现中的普遍支架。因此，我们决定合成一些新的4,5'-双噻唑系列。总共合成了17种化合物，其结构解析基于元素分析（C，H，N，S）和光谱数据（MS和1 H NMR）。使用分光光度法评估了它们对几种革兰氏阳性和革兰氏阴性细菌菌株以及一种真菌菌株（白色念珠菌）的体外抗菌活性。一些化合物对革兰氏阴性大肠杆菌，鼠伤寒沙门氏菌和革兰氏阳性菌表现出中等至良好的抗菌活性。金黄色葡萄球菌和蜡状芽孢杆菌菌株。所有合成的化合物对白念珠菌均具有中度到很好的抑菌活性。
• 以2-噻吩甲醛缩氨基硫脲为配体的铜化合物 及其合成方法
  申请人：广西师范大学

  公开号：CN110790778B

  公开（公告）日：2021-05-28

  本发明公开了一种以2‑噻吩甲醛缩氨基硫脲为配体的铜化合物及其合成方法，合成方法是取氨基硫脲，加入无水乙醇搅拌溶解，溶解后，加入2‑噻吩甲醛，混合均匀，将混合溶液在水浴70℃条件下搅拌，室温挥发，有晶体析出，得到配体；取制得的配体加入无水乙醇搅拌溶解，溶解后，加入CuBr2·2H2O，在水浴70℃条件下搅拌，室温挥发，有晶体析出，得到配体的Cu化合物。本发明进一步对合成的铜化合物进行了体外增殖抑制活性实验，结果表明，合成的系列铜化合物对其体外活性普遍较好，特别是对人T24和HeLa细胞具有高度特异性，表现出很好的抑制活性，并且对人正常细胞毒性作用不大，适用于制备高效，低毒的抗肿瘤药物。