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5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine is a chemical compound with the molecular formula C9H8N4S. It belongs to the class of aromatic compounds known as thiadiazoles and is primarily used in pharmaceutical research and development.

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  • 76074-47-0 Structure
  • Basic information

    1. Product Name: 5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine
    2. Synonyms: 5-(M-tolyl)-1,3,4-thiadiazol-2-aMine
    3. CAS NO:76074-47-0
    4. Molecular Formula: C9H9N3S
    5. Molecular Weight: 191.25286
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 76074-47-0.mol
  • Chemical Properties

    1. Melting Point: 153-156 °C
    2. Boiling Point: 379.0±35.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.281±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    8. Solubility: N/A
    9. PKA: 2.90±0.10(Predicted)
    10. CAS DataBase Reference: 5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine(CAS DataBase Reference)
    11. NIST Chemistry Reference: 5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine(76074-47-0)
    12. EPA Substance Registry System: 5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine(76074-47-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 76074-47-0(Hazardous Substances Data)

76074-47-0 Usage

Uses

Used in Pharmaceutical Research and Development:
5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine is used as a research compound for its potential applications in the pharmaceutical industry due to its unique chemical structure and properties.
Used in Antimicrobial Applications:
5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine is used as an antimicrobial agent for its potential in treating bacterial infections, offering a new avenue for combating resistant strains of bacteria.
Used in Antitumor Applications:
5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine is used as an antitumor agent for its potential in treating cancer, with ongoing research to explore its efficacy and mechanism of action.
Used in Antioxidant and Anti-inflammatory Applications:
5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine is used as an antioxidant and anti-inflammatory agent, with research indicating its potential to mitigate oxidative stress and inflammation, which are implicated in various diseases and conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 76074-47-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,0,7 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 76074-47:
(7*7)+(6*6)+(5*0)+(4*7)+(3*4)+(2*4)+(1*7)=140
140 % 10 = 0
So 76074-47-0 is a valid CAS Registry Number.

76074-47-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine

1.2 Other means of identification

Product number -
Other names 2-Amino-5-m-tolyl-1,3,4-thiadiazol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:76074-47-0 SDS

76074-47-0Relevant articles and documents

An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones

Hosseini, Saedehsadat,Esmaeili, Abbas Ali,Khojastehnezhad, Amir,Notash, Behrouz

, p. 628 - 644 (2021/07/02)

In this research, firstly, some derivatives of sulfur containing [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one have been synthesized and then they were used for the synthesis of novel derivatives of 6′-amino-2,9′-dioxo-2′-phenyl-9′H-spiro[indoline-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine]-7′-carbonitriles via a one-pot three-component condensation reaction of 7-hydroxy-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives, malononitrile and isatin compounds in the presence of DABCO as a organocatalyst and under solvent-free conditions. In this report, a new family of spiro-pyrano-thiadiazolo-pyrimidine derivatives have been synthesized in short reaction times (10–60 min) and good to excellent yields (80–96%). The structures of all synthesized products have been confirmed by IR, 1H NMR, 13C NMR and mass spectrometry, and the structure of one selected product was characterized by single-crystal X-ray diffraction studies as well.

Synthesis and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents

Begari, Eeshwaraiah,Dave, Alpa Y.,Joshi, Deepkumar S.,Parmar, Kokila A.

, p. 273 - 280 (2021/08/03)

A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

-

Paragraph 0095-0097; 0129-0130, (2021/01/30)

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1

N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound

-

Paragraph 0051; 0057; 0090-0092, (2021/06/09)

The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Xue, Wenjie,Li, Xueyao,Ma, Guixing,Zhang, Hongmin,Chen, Ya,Kirchmair, Johannes,Xia, Jie,Wu, Song

, (2020/02/04)

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies

Jakovljevi?, Katarina,Joksovi?, Milan D.,Botta, Bruno,Jovanovi?, Ljiljana S.,Avdovi?, Edina,Markovi?, Zoran,Mihailovi?, Vladimir,Andri?, Marijana,Trifunovi?, Sne?ana,Markovi?, Violeta

, p. 585 - 598 (2019/07/05)

A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am

PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles

Han, Yingzhi,Sun, Yadong,Abdukader, Ablimit,Liu, Bifu,Wang, Duozhi

, p. 3486 - 3491 (2018/09/27)

A highly efficient method for the synthesis of thiadiazole 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 Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.

Synthesis and molecular simulation study of furoic peptidomimetic derivatives as potent aminopeptodase N inhibitors

Gao, Min,He, Junhua,Xu, Weidong,Lai, Xiaoping,Liu, Fen,Tu, Guogang

, p. 123 - 127 (2018/03/25)

The aminopeptidase N (APN) plays a critical role in angiogenesis and is over-expressed in tumor cells. In this paper, we report the synthesis and enzyme inhibition assay of furoic peptidomimetic compounds. These new compounds exhibit potent inhibitory ability toward APN with IC50 values lying in the micromolar level. The binding mode of inhibitors in APN active site was explained by a molecular simulation study. These data reveal that ligand coordinating with the catalytic Zn-ion is very important for inhibitory activities.

Synthesis of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold as insecticidal/acaricidal agents

Lv, Min,Liu, Guangci,Jia, Minghong,Xu, Hui

, p. 88 - 92 (2018/08/21)

In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold were prepared, and their insecticidal and acaricidal activities were evaluated against Mythimna separata and Tetranychus cinnabarinus. Some compounds exhibited potent insecticidal and acaricidal activities. It suggested that R1 as a nitro group and R2 as a fluorine atom, were important for the insecticidal activity; R1 as the electron-donating groups and R2 as the methyl group, were necessary for the acaricidal activity.

Synthesis and biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole

Yang, Ming-Yan,Zhao, Wen,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai

, p. 314 - 318 (2015/04/14)

In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.

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