1,3-噻唑啉-4-酮-2-乙腈 | 74246-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 1,3-噻唑啉-4-酮-2-乙腈
• 英文名称: 2-cyanomethyl-2-thiazolin-4-one
• 英文别名: 2-(4-oxo-4,5-dihydrothiazol-2-yl)acetonitrile；2-cyanomethyl-4-thiazolinone；2-cyanomethyl thiazolidin-4-one；2-cyanomethyl thiazol-4-one；(4-Oxo-4,5-dihydro-1,3-thiazol-2-yl)acetonitrile；2-(4-oxo-1,3-thiazol-2-yl)acetonitrile
• CAS: 74246-64-3
• 化学式: C₅H₄N₂OS
• mdl: MFCD00052566
• 分子量: 140.166
• InChiKey: LXFWWRBPFWGVJT-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R23/24/25
• 危险品运输编号：
  UN 3439
• 海关编码：
  2934100090
• 安全说明：
  S36/37

SDS

Name:	2-(4-oxo-4 5-dihydro-1 3-thiazol-2-yl)acetonitrile 97% Material Safety Data Sheet
Synonym:	1,3-Thiazolin-4-one-2-acetonitril
CAS:	74246-64-3

Section 1 - Chemical Product MSDS Name:2-(4-oxo-4 5-dihydro-1 3-thiazol-2-yl)acetonitrile 97% Material Safety Data Sheet
Synonym:1,3-Thiazolin-4-one-2-acetonitril

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
74246-64-3	2-(4-Oxo-4,5-dihydro-1,3-thiazol-2-yl)	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause 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:

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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:
Vacuum or sweep up material and place into a suitable disposal 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 74246-64-3: 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: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 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: C5H4N2OS
Molecular Weight: 140

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Bases, oxidizing agents, reducing agents, amines.
Hazardous Decomposition Products:
Hydrogen cyanide, 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# 74246-64-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(4-Oxo-4,5-dihydro-1,3-thiazol-2-yl)acetonitrile - 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: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
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.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 74246-64-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 74246-64-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 74246-64-3 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：

  1,3-噻唑啉-4-酮-2-乙腈 在 乙酸铵 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 2-amino-6-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-3-(4-oxothiazolidin-2-yl)pyridine
  参考文献：
  名称：

  1-(2,4-dimethoxyphenyl)-3-aryl-prop-2-ene-1-ones 作为环状变压器在制备杂环化合物中的应用及其潜在的生物活性

  摘要：

  XI与过量乙酸铵的融合产生2-氨基吡啶衍生物XII和2-氨基四氢吡啶衍生物XIII。通过在 0°C 下用 HNO2 处理重氮化 XII 产生重氮氯化物衍生物 XIV，该衍生物与酚类化合物发生偶联反应以产生偶氮分散染料 XV。XVIII的碱水解得到相应的酸XX，其通过融合与肼反应产生二氮杂芴酮衍生物XXI。所得产物的结构经元素分析、红外、1H-NMR、13C-NMR和质谱证实。筛选了一些合成产品的生物活性。XVIII的碱水解得到相应的酸XX，其通过融合与肼反应得到二氮杂芴酮衍生物XXI。所得产物的结构经元素分析、红外、1H-NMR、13C-NMR和质谱证实。筛选了一些合成产品的生物活性。XVIII的碱水解得到相应的酸XX，其通过融合与肼反应产生二氮杂芴酮衍生物XXI。所得产物的结构经元素分析、红外、1H-NMR、13C-NMR和质谱证实。筛选了一些合成产品的生物活性。

  DOI：

  10.1080/10426500490257041
• 作为产物：
  描述：

  巯基乙酸 、 丙二腈 反应 0.5h， 生成 1,3-噻唑啉-4-酮-2-乙腈
  参考文献：
  名称：

  合成一些新的噻唑并[3,2-a]吡啶和相关的杂环系统。

  摘要：

  已经制备了新的2，7-二取代的5-氨基-6，8-二氰基-2，3-二氢-3-氧代噻唑并[3，2-a]吡啶。它们与甲酰胺，亚硝酸和原甲酸三乙酯环合，得到一系列含有稠合的嘧啶和三嗪环的多环杂环。还进行了抗真菌试验。

  DOI：

  10.1016/s0014-827x(99)00130-5

文献信息

• One-pot strategy for thiazole tethered 7-ethoxy quinoline hybrids: Synthesis and potential antimicrobial agents as dihydrofolate reductase (DHFR) inhibitors with molecular docking study
  作者：Yousry A. Ammar、Sondos M.A. Abd El-Hafez、Sadia A. Hessein、Abeer M. Ali、Ahmed A. Askar、Ahmed Ragab

  DOI：10.1016/j.molstruc.2021.130748

  日期：2021.10

  challenge can be solved by discovering new targets and inhibitors. The current study involved synthesis quinoline based thiazole analogues for quinoline antibiotic class using classic organic synthesis. The designed derivatives were tested against eight standard microbial pathogens. Among them, seven derivatives showed good antimicrobial activity with MIC and MBC values ranged between (0.97-62.5) µg/mL

  在世界各地，尤其是发展中国家，对人类健康的主要威胁之一是由于滥用抗生素而导致的抗生素耐药性。这一挑战可以通过发现新的靶点和抑制剂来解决。目前的研究涉及使用经典有机合成合成喹啉类抗生素的喹啉类噻唑类似物。针对八种标准微生物病原体对设计的衍生物进行了测试。其中，7 种衍生物表现出良好的抗菌活性，MIC 和 MBC 值分别介于 (0.97-62.5) µg/mL 和 (1.94-118.7) µg/mL 之间。另外，活性衍生物显示出对三种MDR细菌染色的良好活性。化合物11b和5a表现出对金黄色葡萄球菌最具活性的衍生物和大肠杆菌，MIC (1.95-7.81) µg/mL 和 MBC (3.31-15.62) µg/mL 其次是其他衍生物，与环丙沙星和万古霉素相比。此外，化合物6、11c和15出现了对 MDR铜绿假单胞菌最具活性的衍生物，其 MIC 和 MBC 值低于 10 µg/mL。这些衍生物被认为通过抑制显示
• Synthesis of Novel 4-Thiazolidinones Linked by an Aryl Spacer to a 1,2,4-Triazine Moiety
  作者：Hamdy Khamees Thabet、Mustafa Turki Ubeid、Said Ahmed El-Feky

  DOI：10.3184/174751915x14412838239915

  日期：2015.10

  A series of potentially biologically active hydrazones, Schiff's base and hybrid thiazolidine-triazine derivatives have been prepared from 4-[(5,6-diphenyl-1,2,4-triazin-3-yl)thio]-benzaldehyde. The latter was prepared by reacting 5,6-diphenyl-1,2,4-triazine-3(2H)-thione with 4-fluorobenzaldehyde. The derivatives were then prepared by condensation of the aldehyde with hydrazines, aniline and various thiazolidin-4-ones. Their structures were established by C,H,N analyses, IR and NMR spectra.

  由 4-[(5,6-二苯基-1,2,4-三嗪-3-基)硫]-苯甲醛制备了一系列具有潜在生物活性的酰肼、席夫碱和噻唑烷-三嗪杂化衍生物。后者是通过 5,6-二苯基-1,2,4-三嗪-3(2H)-硫酮与 4-氟苯甲醛反应制备的。然后通过醛与肼类、苯胺和各种噻唑啉-4-酮缩合制备衍生物。通过 C、H、N 分析、红外光谱和核磁共振光谱确定了它们的结构。
• Synthesis of novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives as cyclooxygenase‐2 inhibitors
  作者：Abida Khan、Anupama Diwan、Hamdy K Thabet、Mohd Imran

  DOI：10.1002/ddr.21655

  日期：2020.8

  N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazines as COX‐2 inhibitors have been developed (Supplementary material Appendix 1). The novel aldehyde 3 was prepared by reacting 6‐phenylpyridazin‐3(2H)‐one with 4‐fluorobenzaldehyde. The aldehyde 3 was reacted with different hydrazines and thiazolidin‐4‐ones to obtain the novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives. These were assessed for their anti‐inflammatory

  一些新型的非致溃疡性 N-取代苯基-6-氧代-3-苯基哒嗪作为 COX-2 抑制剂被开发出来（补充材料附录 1）。通过 6-苯基哒嗪-3( 2H )-one 与 4-氟苯甲醛反应制备了新型醛3。醛3与不同的肼和噻唑啉-4-酮反应得到新型N-取代苯基-6-氧代-3-苯基哒嗪衍生物。评估了它们的抗炎潜力和胃溃疡形成作用。还进行了分子对接研究。光谱数据与化合物的分配结构一致。化合物4a (IC 50 = 17.45 nm；p < .05)，4b (IC 50 = 17.40 nm; p < .05)、5a (IC 50 = 16.76 nm; p < .05) 和10 (IC 50 = 17.15 nm; p < .05) 比塞来昔布（IC 50 = 17.79 nm；p < .05）。这些发现与4a、4b、5a和10的分子对接研究一致。在体内的抗炎轮廓图4a，图4b，图5a，和10也优于塞来昔
• Anti-inflammatory and Anti-ulcer Activities of New Fused Thiazole Derivatives Derived from 2-(2-Oxo-2H-chromen-3-yl)thiazol-4(5H)-one
  作者：Rafat Mohareb、Fatima Al-Omran、Mahmoud Abdelaziz、Rehab Ibrahim

  DOI：10.17344/acsi.2017.3200

  日期：2017.6.15

  The reaction of the 2-(4-oxo-4,5-dihydrothiazol-2-yl)acetonitrile (1) with salicylaldehyde (2) in 1,4-dioxane containing a catalytic amount of piperidine gave the coumarin derivative 3. The latter reacted with different reagents to give pyrano[4,5-b]thiazole, pyrido[4,5-b]thiazole and thieno[5,4-b]thiazole dereivatives. The anti-inflammatory and anti-ulcer activities of the newly synthesized products

  2-（4-氧代-4,5-二氢噻唑-2-基）乙腈（1）与水杨醛（2）在含有催化量哌啶的1,4-二恶烷中反应，得到香豆素衍生物3。后者与不同的试剂反应，得到吡喃并[4,5-b]噻唑，吡啶并[4,5-b]噻唑和噻吩并[5,4-b]噻唑去污剂。评价了新合成产物的抗炎和抗溃疡活性，结果表明与其余化合物相比，化合物7a，8a，10b，13b，15b，18a，19b，19c和19d表现出更高的活性。除此之外，还研究了这种活性化合物对虾幼虫的毒性，其中化合物10b，18a，19c和19d对被测生物无毒。
• Reactions with Thiaxanthen-9-ol: New Thiaxanthene Derivatives with Molluscicidal and Nematocidal Activity
  作者：Ibrahim A. El-Sakka、Ibrahim F. Zeid、Hamed M. Abdel-Bary、Ahmed E. S. Abdel-Mageed

  DOI：10.1002/ardp.19943270303

  日期：——

  Thiaxanthen‐9‐ol (1) was condensed with nitriles 2a‐e to yield the thiaxanthen‐9‐yl‐acetonitriles 3a‐e. With the thiols 7a‐d, 1 yielded the thioethers 8a‐d.

  Thiaxanthen - 9 - ol (1) 与腈类 2a -e 缩合得到 thiaxanthen - 9-yl - 乙腈 3a - e。使用硫醇 7a-d，1 生成硫醚 8a-d。