2-氨基-5-(4-氯苯基)-1,3,4-噻二唑 | 28004-62-8

• 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: 2-氨基-5-(4-氯苯基)-1,3,4-噻二唑
• 中文别名: 5-(4-氯苯基)-[1,3,4]噻二唑-2-胺
• 英文名称: 2-amino-5-(4-chlorophenyl)-1,3,4-thiadiazole
• 英文别名: 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole；5-(4-chlorophenyl)-1,3,4-thiadiazol-2-amine；5-(4-chlorophenyl)-1,3,4-thiadiazole-2-amine；2-Amino-5-(p-chlor-phenyl)-1,3,4-thiadiazol
• CAS: 28004-62-8
• 化学式: C₈H₆ClN₃S
• mdl: MFCD00980966
• 分子量: 211.675
• InChiKey: OAVULPOOAHQYDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  229-233 °C (lit.)
• 沸点：
  383.9±44.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密的容器中。应储存在阴凉、干燥的地方。

SDS

Name:	5-(4-Chlorophenyl)-1,3,4-Thiadiazole-2-Ylamine, 98% Material Safety Data Sheet
Synonym:
CAS:	28004-62-8

Section 1 - Chemical Product MSDS Name: 5-(4-Chlorophenyl)-1,3,4-Thiadiazole-2-Ylamine, 98% Material Safety Data Sheet
Synonym:

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
28004-62-8	5-(4-Chlorophenyl)-1,3,4-Thiadiazole-2	98	unlisted

+++++
Hazard Symbols: 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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
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 or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 28004-62-8: 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: Not available.
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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:
Molecular Weight:

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 28004-62-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(4-Chlorophenyl)-1,3,4-Thiadiazole-2-Ylamine - 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 No information available. IMO No information available. RID/ADR No information available.

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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 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# 28004-62-8: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 28004-62-8 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 28004-62-8 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/18/1999 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-5-(4-氯苯基)-1,3,4-噻二唑 在 硫酸 、 硝酸 作用下， 以 吡啶 为溶剂， 反应 11.0h， 生成 2-amino-5-(3-nitro-4-piperazinylphenyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Chauhan, P. M. S.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1146 - 1149

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯甲酸甲酯 在 盐酸 、 硫酸 、 肼 作用下， 以 水 为溶剂， 生成 2-氨基-5-(4-氯苯基)-1,3,4-噻二唑
  参考文献：
  名称：

  N-烷基-3,6-二芳基-[1,2,4]三唑并[4,3-b][1,2,4]三嗪-7-胺在无溶剂条件下的高效三组分合成

  摘要：

  一种简单、高效、环保的合成N-烷基-3,6-二芳基[1,2,4]三唑并[4,3-b][1,2,4]triazin-7-的方法基于 5-芳基-4H-1,2,4三唑-3,4-二胺、异氰化物和醛在无溶剂条件下三组分反应的胺。以中等至良好的收率获得产品并且处于高纯度状态。

  DOI：

  10.24820/ark.5550190.p010.175

文献信息

• Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones
  作者：Varsha Jatav、Pradeep Mishra、Sushil Kashaw、J.P. Stables

  DOI：10.1016/j.ejmech.2007.02.004

  日期：2008.1

  anticonvulsant activity in one or more test models. All except 4e and 4f exhibited significant sedative-hypnotic activity via actophotometer screen. CNS depressant activity screened with the help of the forced swim pool method resulted into some potent compounds. From the experimental observation it can be concluded that synthesized compounds exhibited relatively better sedative-hypnotic and CNS depressant activities

  合成了一系列新型的3- [5-取代苯基-1,3,4-噻二唑-2-基] -2-苯乙烯基喹唑啉-4（3H）-并评估其抗惊厥，镇静催眠和中枢神经系统抑制活性。在以30、100和300mg / kg体重腹腔注射小鼠后，在最大电击诱发癫痫发作（MES）和皮下戊四氮（scPTZ）诱发的癫痫发作模型中检查了2-苯乙烯基喹唑啉-4（3H）-衍生物。老鼠。使用转子法评估神经毒性。在18种化合物中，只有4a，4d，4e，4j和4k在一个或多个测试模型中显示出抗惊厥活性。通过光度计屏幕，除4e和4f外，所有其他药物均显示出明显的镇静催眠活性。借助于强制游泳池法筛选的中枢神经系统抑制剂活性产生了一些有效的化合物。
• Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl) 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones
  作者：Varsha Jatav、Sushil Kashaw、Pradeep Mishra

  DOI：10.1007/s00044-007-9047-2

  日期：2008.6

  3-[5-substituted phenyl-1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones were synthesized and evaluated for antibacterial activity against pathogenic strains of Staphylococcus aureus (MTCC no. 96), Bacillus subtilis (MTCC no. 619), Pseudomonas aeruginosa (MTCC no. 424) and Escherichia coli (MTCC no. 40) and antifungal activity against Aspergillus niger, Candida albicans and Fusarium oxysporum

  合成了一系列新型的3- [5-取代的苯基-1,3,4-噻二唑-2-基] -2-苯乙烯基喹唑啉-4（3H）-，并评估了其对 金黄色葡萄球菌 致病菌株的抗菌活性 （ MTCC编号96）， 枯草芽孢杆菌 （MTCC编号619）， 铜绿假单胞菌 （MTCC编号424）和 大肠杆菌 （MTCC编号40）以及对 黑曲霉，白色念珠菌 和 尖孢镰刀菌的 抗真菌活性 。采用杯板法测定化合物的最小抑菌浓度（MIC）值。一些化合物表现出与诺氟沙星相当的活性。本报告揭示了合成的2-苯乙烯基-喹唑啉-4（3H）-一具有比抗真菌活性更好的抗菌作用。
• Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones
  作者：Solange C. Martins、Vânia C. Desoti、Danielle Lazarin-Bidóia、Fábio Vandresen、Cleuza C. da Silva、Tania Ueda-Nakamura、Sueli de O. Silva、Celso V. Nakamura

  DOI：10.1007/s00044-016-1561-7

  日期：2016.6

  selectivity indexes. The vast majority of the monoterpene derivatives, substituted by R-(+)-limonene, presented better anti-T. cruzi activity than the non-substituted compounds. Regarding the cytotoxic profile, the compounds without the monoterpene R-(+)-limonene were, in general, less toxic. The present findings indicate that the 1,3,4-thiadiazoles derivatives of R-limonene have potential trypanocidal activity

  在这项研究中，我们合成了一系列R -（+）-mon烯苯甲醛-硫代半咔唑酮（2a - k）的1,3,4-噻二唑衍生物。我们还确定了LLCMK 2细胞的细胞毒性以及克氏锥虫，这些合成化合物以及一系列不含单萜R -（+）-柠檬烯（4a的1,3,4-噻二唑– k）。1,3,4-噻二唑化合物显示出显着的锥虫杀灭活性和高选择性指数。被R -（+）-柠檬烯取代的绝大多数单萜衍生物表现出更好的抗T.活性高于非取代化合物。关于细胞毒性特征，通常不含单萜R -（+）-柠檬烯的化合物毒性较小。目前的发现表明，R-柠檬烯的1,3,4-噻二唑衍生物具有潜在的锥虫杀虫活性，因此有必要进行进一步的研究以更好地了解这些物质对克氏锥虫的作用机理。
• PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
  作者：Yingzhi Han、Yadong Sun、Ablimit Abdukader、Bifu Liu、Duozhi Wang

  DOI：10.1007/s10562-018-2541-y

  日期：2018.11

  derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields.Graphical AbstractA highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling

  摘要 开发了一种利用原位生成的高价碘（III）试剂，通过氨基硫脲的分子内氧化偶联合成噻二唑衍生物的高效方法。该协议可以顺利进行，并以中等至优异的收率提供各种噻二唑衍生物。图形摘要一种高效的合成噻二唑衍生物的方法通过 PhI 催化分子内氧化偶联氨基硫脲。
• Synthesis and Biological Evaluation of Novel Carbazole Hybrids as Promising Antimicrobial Agents
  作者：Mahamadhanif S. Shaikh、Balakumar Chandrasekaran、Mahesh B. Palkar、Ashish M. Kanhed、Afsana Kajee、Koleka P. Mlisana、Parvesh Singh、Meenu Ghai、Mavela Cleopus Mahlalela、Rajshekhar Karpoormath

  DOI：10.1002/cbdv.201900550

  日期：2020.5

  of series 1 displayed notable antimicrobial activity (MIC: 6.25 μg/mL) against clinical isolates of C. albicans and C. neoformans (MIC: 12.5 μg/mL). From the second series, four compounds exhibited significant antifungal and antibacterial activity, especially against C. neoformans and S. aureus. The most active compound of series 2 displayed a prominent antimicrobial activity against C. neoformans

  8-甲氧基-N-取代-9H-咔唑-3-甲酰胺（系列1）和咔唑基取代的若丹宁（系列2）的两个系列咔唑类似物通过简便的合成路线合成。评估了这两个系列的所有最终化合物对四种真菌（白色念珠菌、新型隐球菌、热带隐球菌和黑曲霉）和四种细菌（金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌和铜绿假单胞菌）的初步体外抗真菌和抗菌活性) 应变，分别。在测试的化合物中，系列 1 的三种化合物显示出有希望的抗真菌和抗菌活性，尤其是对新型隐球菌和金黄色葡萄球菌。此外，系列 1 的一种化合物显示出显着的抗微生物活性（MIC：6.25 μg/mL），对临床分离株 C. 白色念珠菌和新型隐球菌（MIC：12.5 μg/mL）。在第二个系列中，四种化合物表现出显着的抗真菌和抗菌活性，尤其是对新型隐球菌和金黄色葡萄球菌。系列 2 中活性最强的化合物分别显示出对新型隐球菌（MIC：3.125 μg/mL）和金黄色葡萄球菌（MIC：1.56