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Cas Database

76074-47-0

76074-47-0

Identification

  • Product Name:5-M-Tolyl-[1,3,4]thiadiazol-2-ylaMine

  • CAS Number: 76074-47-0

  • EINECS:

  • Molecular Weight:191.257

  • Molecular Formula: C9H9N3S

  • HS Code:2934999090

  • Mol File:76074-47-0.mol

Synonyms:5-(M-tolyl)-1,3,4-thiadiazol-2-aMine

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:5-(m-Tolyl)-1,3,4-Thiadiazol-2-amine
  • Packaging:1g
  • Price:$ 285
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:5-m-Tolyl-[1,3,4]thiadiazol-2-ylamine
  • Packaging:500mg
  • Price:$ 65
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:5-m-Tolyl-[1,3,4]thiadiazol-2-ylamine
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  • Price:$ 99
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  • Manufacture/Brand:Chemenu
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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  • Manufacture/Brand:Chemenu
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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  • Manufacture/Brand:Chemenu
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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  • Manufacture/Brand:Chemenu
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:5-(3-METHYLPHENYL)-1,3,4-THIADIAZOL-2-AMINE 95.00%
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(m-tolyl)-1,3,4-Thiadiazol-2-amine 95%
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Relevant articles and documentsAll total 25 Articles be found

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.

Process route upstream and downstream products

Process route

thiosemicarbazide
79-19-6

thiosemicarbazide

m-Toluic acid
99-04-7

m-Toluic acid

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With trichlorophosphate; at 0 - 70 ℃; for 4.5h;
85%
With trichlorophosphate; Irradiation;
With trichlorophosphate; Microwave irradiation;
With trichlorophosphate; at 0 - 5 ℃; Reflux;
With trichlorophosphate; at 100 ℃; for 4h;
With trichlorophosphate; at 0 ℃; Reflux; Inert atmosphere;
thiosemicarbazide; m-Toluic acid; With trichlorophosphate; at 0 ℃; Reflux; Inert atmosphere;
With sodium hydroxide; In water; pH=8 - 9;
With trichlorophosphate; In 1,4-dioxane; at 0 - 75 ℃; for 2.33333h;
With trichlorophosphate;
With trichlorophosphate;
thiosemicarbazide; m-Toluic acid; With trichlorophosphate; at 75 ℃; for 0.5h;
With water; for 4h; Reflux;
With trichlorophosphate; at 75 - 110 ℃; for 4.5h;
m-Toluic acid; With trichlorophosphate; at 20 ℃; for 0.333333h;
thiosemicarbazide; for 1h; Reflux;
With sulfuric acid; at 70 - 80 ℃; for 7h;
thiosemicarbazide
79-19-6

thiosemicarbazide

3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With trifluoroacetic acid; at 80 ℃; Reflux;
56%
thiosemicarbazide; 3-Methylbenzonitrile; With trifluoroacetic acid; at 75 ℃; for 6h;
With ammonium hydroxide; In water; at 20 ℃;
2-(3-methylbenzylidene)hydrazinocarbothioamide
5706-82-1

2-(3-methylbenzylidene)hydrazinocarbothioamide

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With iodosylbenzene; dihydrogen peroxide; acetic acid; In dimethyl sulfoxide; at 60 ℃; for 4h; Green chemistry;
2-(3-methylbenzoyl)hydrazinecarbothioamide
881-73-2

2-(3-methylbenzoyl)hydrazinecarbothioamide

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With sulfuric acid;
45%
With sulfuric acid;
With PPA; at 100 ℃; for 1h;
m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium acetate / water; ethanol / 0.25 h / 20 °C
2: acetic acid; iodosylbenzene; dihydrogen peroxide / dimethyl sulfoxide / 4 h / 60 °C / Green chemistry
With iodosylbenzene; dihydrogen peroxide; sodium acetate; acetic acid; In ethanol; water; dimethyl sulfoxide;
thiosemicarbazide
79-19-6

thiosemicarbazide

5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With pyridine;
With pyridine;
5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

Conditions
Conditions Yield
With trifluoroacetic acid; at 70 ℃; for 8h;
49.2%
Thiosemicarbazid, 3-Methyl-benzimidsaeureester-hydrochlorid, Py.,Sieden;
Thiosemicarbazid, m-Toluoylsaeure-aethylester-imid*HCl, sd.Py;
With trichlorophosphate; at 75 ℃; for 3h;
With water; at 100 ℃; for 4h;
5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

malonic acid bis-(2,4,6-trichloro-phenyl) ester
15781-70-1

malonic acid bis-(2,4,6-trichloro-phenyl) ester

7-hydroxy-2-(m-tolyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

7-hydroxy-2-(m-tolyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Conditions
Conditions Yield
In acetone; at 20 ℃; for 3h;
5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

2-(3-Oxo-3h-benzo[d]isothiazol-2-yl)-acetic acid
82152-06-5

2-(3-Oxo-3h-benzo[d]isothiazol-2-yl)-acetic acid

2-(3-oxo-1,2-benzothiazol-2(3H)-yl)-N-(5-(m-tolyl)-1,3,4-thiadiazole-2-yl)acetamide
1609552-01-3

2-(3-oxo-1,2-benzothiazol-2(3H)-yl)-N-(5-(m-tolyl)-1,3,4-thiadiazole-2-yl)acetamide

Conditions
Conditions Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dimethyl sulfoxide; at 20 ℃; for 20h;
82%
5-(3-methylphenyl)-1,3,4-thiadiazol-2-amine
76074-47-0

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

12-N-p-methylbenzyl matrinic acid
1345730-92-8

12-N-p-methylbenzyl matrinic acid

C<sub>32</sub>H<sub>41</sub>N<sub>5</sub>OS

C32H41N5OS

Conditions
Conditions Yield
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;
56%

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  • SAGECHEM LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86818502
  • Emails:will@sagechem.com
  • Main Products:28
  • Country:China (Mainland)
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