4-丙烯基硫代氨基脲 | 3766-55-0

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-丙烯基硫代氨基脲
• 中文别名: 4-烯丙基氨基硫脲；4-烯丙基硫氨基脲
• 英文名称: 4-allyl-3-thiosemicarbazide
• 英文别名: 4-allylthiosemicarbazide；N-(prop-2-en-1-yl)hydrazinecarbothioamide；N-allylhydrazinecarbothioamide；N-allylthiosemicarbazide；1-amino-3-prop-2-enylthiourea
• CAS: 3766-55-0
• 化学式: C₄H₉N₃S
• mdl: MFCD00007619
• 分子量: 131.202
• InChiKey: CZLPCLANGIXFIE-UHFFFAOYSA-N

物化性质

• 熔点：
  93-96 °C(lit.)
• 沸点：
  209.8±33.0 °C(Predicted)
• 密度：
  1.142 (estimate)
• 溶解度：
  可溶于丙酮（少量）、DMSO（少量）
• 稳定性/保质期：

  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品运输编号：
  2811
• WGK Germany：
  3
• RTECS号：
  VT3000000
• 海关编码：
  2930909090
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38,R25
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

Name:	4-Allylthiosemicarbazide 97% Material Safety Data Sheet
Synonym:	Hydrazinecarbothioamide, N-2-Propenyl-; Semicarbazide, 4-Allyl-3-Thio-
CAS:	3766-55-0

Section 1 - Chemical Product MSDS Name:4-Allylthiosemicarbazide 97% Material Safety Data Sheet
Synonym:Hydrazinecarbothioamide, N-2-Propenyl-; Semicarbazide, 4-Allyl-3-Thio-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3766-55-0	4-Allylthiosemicarbazide	97	223-186-7

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.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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:
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# 3766-55-0: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white crystalline powder
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 93.00 - 96.00 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: H2C=CHCH2NHCSNHNH2
Molecular Weight: 131.20

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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:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3766-55-0: VT3000000 LD50/LC50:
Not available.
Carcinogenicity:
4-Allylthiosemicarbazide - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 3766-55-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3766-55-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3766-55-0 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

制备方法与用途

类别：有毒物品

• 毒性分级：高毒
• 急性毒性：静脉注射-小鼠 LD50 为 56 毫克/公斤
• 可燃性危险特性：可燃；燃烧时产生有毒氮氧化物和硫氧化物烟雾
• 储运特性：应存放在库房中，保持通风、低温干燥，并与食品原料分开存放

灭火剂：

• 干粉
• 泡沫
• 砂土
• 二氧化碳
• 雾状水

反应信息

• 作为反应物：
  描述：

  4-丙烯基硫代氨基脲 在 盐酸 、 potassium nitrite 作用下， 生成 N-allyl-1,2,3,4-thiatriazol-5-amine
  参考文献：
  名称：

  Freund; Schwarz, Chemische Berichte, 1896, vol. 29, p. 2499

  摘要：

  DOI：
• 作为产物：
  描述：

  天然芥菜籽油 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以64%的产率得到4-丙烯基硫代氨基脲
  参考文献：
  名称：

  基于[Cu 2（amtd）2 ] 2+（amdd = 2-烯丙基氨基-5-甲基-1,3,4-噻二唑）二聚体的溶剂化六氟硅酸铜（I）配合物

  摘要：

  [Cu 2（amdt）2 ] SiF 6 ·C 6 H 6和[Cu 2（amdt）2（H 2 O）2 ] SiF 6 ·CH 3 CN·2H 2 O（amdt = 2-烯丙基氨基-5-甲基-1,3,4-噻二唑）是通过交流电化学合成而获得的，其起始原料是水-乙腈-苯混合物，其中含有2-烯丙基氨基-5-甲基-1,3,4-噻二唑和CuSiF 6 ·4H 2O.在乙腈-苯amdt溶液的整齐倾倒层下面对饱和的六氟硅酸铜水溶液进行电化学还原，导致形成晶体[Cu 2（amdt）2 ] SiF 6 ·C 6 H 6。相同的混合物的对其进行电化学还原之前的初始搅拌导致的形成物[Cu 2（AMDT）2（H 2 O）2 ]的SiF 6 ·CH 3 CN·2H 2 O的乙腈呆滞水解在[Cu 2（amdt）2 ] SiF密闭试管中放置2年以上母液中的6 ·C 6 H 6晶体导致[Cu 2 L 2（H 2 O）2 ]

  DOI：

  10.1016/j.jorganchem.2016.03.001

文献信息

• Synthesis, Characterisation, and Antifungal Activities of Novel Benzodiazaborines
  作者：Jiyoung Yang、Brandon J. Johnson、Allan A. Letourneau、Christopher M. Vogels、Andreas Decken、Felix J. Baerlocher、Stephen A. Westcott

  DOI：10.1071/ch14534

  日期：——

  Eight new fluoro- and methoxy-substituted benzodiazaborines have been prepared by a simple condensation reaction in high-to-excellent yields. All new compounds have been characterised by several physical methods, including X-ray diffraction studies on three examples. All new compounds were examined for antifungal activities against five species of potentially pathogenic fungi (Aspergillus niger, Aspergillus fumigatus, Rhizoctonia solani, Verticillium albo-atrum, and Verticillium dahliae). While substitution of the aromatic group derived from the 2-formylphenylboronic acid group had an effect on bioactivities, substitution on the parent thioamide C(=S)NH2 group of the starting thiosemicarbazide greatly reduced activities.

  通过简单的缩合反应，我们制备出了八种新的氟代和甲氧基代苯并二氮硼烷，而且产量极高。所有新化合物都通过多种物理方法进行了表征，包括对三个实例进行了 X 射线衍射研究。所有新化合物都对五种潜在致病真菌（黑曲霉、烟曲霉、根瘤菌、轮枝菌和大丽花轮枝菌）进行了抗真菌活性检测。虽然 2-甲酰基苯硼酸基团衍生的芳香基团的取代对生物活性有影响，但起始硫代氨基甲酰肼的母硫酰胺 C(=S)NH2 基团的取代却大大降低了活性。
• Synthesis of isoflavene-thiosemicarbazone hybrids and evaluation of their anti-tumor activity
  作者：Eugene M.H. Yee、Miriam B. Brandl、David StC Black、Orazio Vittorio、Naresh Kumar

  DOI：10.1016/j.bmcl.2017.04.002

  日期：2017.6

  glioblastoma U87 cancer cell lines. The mono-substituted hybrids exhibited potent anti-proliferative activity against all three cancer cell lines, while the di-substituted hybrids were less active. Selected mono-substituted hybrids were further investigated for their cytotoxicity against normal MRC-5 human lung fibroblast cells, which identified two hybrids with superior selectivity for cancer cells over normal

  苯氧二酚是具有有效的抗肿瘤活性的异黄酮。在这项研究中，通过苯氧酚与硫代氨基脲的缩合反应合成了一系列新颖的单取代和二取代的苯氧二醇-硫代半脲杂化物。评估了杂种对神经母细胞瘤SKN-BE（2）C，三阴性乳腺癌MDA-MB-231和胶质母细胞瘤U87癌细胞系的体外抗增殖活性。单取代的杂种对所有三种癌细胞系表现出有效的抗增殖活性，而双取代的杂种则活性较低。进一步研究了选定的单取代杂种对正常MRC-5人肺成纤维细胞的细胞毒性，与酚氧二醇相比，它鉴定了两种对癌细胞具有比普通细胞优越的选择性的杂种。这表明单取代的苯氧二酚-硫代半碳杂化物杂化物作为抗癌剂具有广阔的发展潜力。
• Dipyridyl Thiosemicarbazone Chelators with Potent and Selective Antitumor Activity Form Iron Complexes with Redox Activity
  作者：Des R. Richardson、Philip C. Sharpe、David B. Lovejoy、Dakshita Senaratne、Danuta S. Kalinowski、Mohammad Islam、Paul V. Bernhardt

  DOI：10.1021/jm0606342

  日期：2006.11.1

  reactions, and antiproliferative activity against tumor cells. The higher antiproliferative efficacy of the HDpT series of chelators relative to the related di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues can be ascribed, in part, to the redox potentials of their Fe complexes which lead to the generation of reactive oxygen species. The most effective HDpT ligands as antiproliferative agents

  铁（Fe）螯合剂用于癌症治疗的开发引起了人们的极大兴趣。我们开发了一系列的二-2-吡啶基酮硫代半碳酮（HDpT）配体，这些配体在体外和体内均显示出明显的选择性抗肿瘤活性。在这项研究中，我们评估了这些配体及其铁配合物的化学和生物学特性，以了解其明显的活性。这包括检查其溶液化学，电化学，介导氧化还原反应的能力以及对肿瘤细胞的抗增殖活性。相对于相关的二-2-吡啶基酮异烟酰yl（HPKIH）类似物，HDpT系列螯合剂具有更高的抗增殖功效，这在一定程度上可归因于其Fe络合物的氧化还原电位，从而导致了活性氧的产生。 。
• Pyridazines. 63. Novel thiosemicarbazones derived from formyl- and acyldiazines: synthesis, effects on cell proliferation, and synergism with antiviral agents
  作者：Johnny Easmon、Gottfried Heinisch、Wolfgang Holzer、Brigitte Rosenwirth

  DOI：10.1021/jm00095a027

  日期：1992.8

  with the above mentioned antiviral drugs. Our results do not support the previously expressed opinion that TSC's are selective antiviral agents. In our test systems no evidence for inhibition of virus-induced cytopathic effect was obtained. The TSC derivatives exhibited a broad range of cytotoxic effects, some at concentrations considerably below those reported to have antiviral efficacy. Several of our

  衍生自各种烷基二嗪基（3-哒嗪基，4-嘧啶基，2-吡嗪基）酮和3-哒嗪甲醛的一系列新型硫代半咔唑（TSC）的合成及其对单纯疱疹病毒（HSV）和人类免疫缺陷病毒（HIV）的评估）以及确定其细胞毒性的方法。此外，还研究了这种TSC与著名的抗病毒药无环鸟苷（ACV）和3'-叠氮基3'-脱氧胸苷（AZT）联合使用的效果。在我们的实验条件下，即确定病毒对HSV-1感染HUT78细胞和MT-1细胞感染HIV-1的细胞病变作用，任何TSC都无法检测到抗病毒活性。然而，观察到了对这些快速生长的T4淋巴细胞细胞系增殖的显着影响。可以建立关于这些细胞毒性作用的明确的结构-活性关系：与吡啶，吡嗪或嘧啶衍生的TSC相比，所研究的大多数3-哒嗪基同类物的细胞毒性较小；在这些化合物中将甲基引入哒嗪系统的C-6或延长酰基部分基本上没有影响；所有带有N，N-二甲基氨基或环氨基取代基的化合物的毒性要比带有NH 2或NHR取
• A new therapeutic approach in Alzheimer disease: Some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics
  作者：Nesrin Gökhan-Kelekçi、Samiye Yabanoğlu、Esra Küpeli、Umut Salgın、Özen Özgen、Gülberk Uçar、Erdem Yeşilada、Engin Kendi、Akgül Yeşilada、A. Altan Bilgin

  DOI：10.1016/j.bmc.2007.06.004

  日期：2007.9.1

  isoforms. All the synthesized compounds were also tested for their in vivo antiinflammatory activity by two different bioassays namely, carrageenan-induced oedema and acetic acid-induced increase in capillary permeability in mice. In addition, analgesic and ulcerogenic activities were determined. The combined antiinflammatory data from in vivo animal models showed that compound 3k exhibited anti-inflammatory

  人口中预期寿命的增加使阿尔茨海默氏病（AD）成为日益严重的公共卫生问题。迫切需要找到预防和延缓疾病的方法。结果表明，单胺氧化酶-B（MAO-B）抑制剂和抗炎药可能有效治疗AD。因此，合成了一系列新型的1-硫代氨基甲酰基-3-取代的苯基-5-（2-吡咯基）-4,5-二氢-（1H）-吡唑衍生物作为有希望的MAO-B抑制剂，并研究了其抑制能力。单胺氧化酶（MAO）的A和B同工型的选择性活性。大多数合成的化合物对MAO-A（化合物3e-3h）和MAO-B（化合物3i-3l）同工型均显示高活性。还通过两种不同的生物测定法测试了所有合成的化合物的体内抗炎活性：角叉菜胶引起的水肿和乙酸引起的小鼠毛细血管通透性增加。此外，还确定了镇痛和促溃疡活性。来自体内动物模型的综合抗炎数据显示，化合物3k具有与消炎痛相当的抗炎活性，且无致溃疡作用。由于化合物3k同时具有抗炎镇痛活性和MAO-B抑制作用，因此需要进一步的详细研究。