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ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE is a pyrazole derivative chemical compound characterized by the molecular formula C15H16N4O2. It features an ethyl ester group and an amino group attached to a 1,4-disubstituted phenyl ring, which endows it with unique biological activities and potential as a building block for the synthesis of bioactive molecules. Due to its properties, it holds promise in the pharmaceutical and agrochemical industries, although it requires careful handling and usage to mitigate any associated hazards.

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  • 15001-11-3 Structure
  • Basic information

    1. Product Name: ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE
    2. Synonyms: SALOR-INT L251453-1EA;ETHYL 5-AMINO-1-P-TOLYL-1H-PYRAZOLE-4-CARBOXYLATE;ETHYL 5-AMINO-1-P-TOLYLPYRAZOLE-4-CARBOXYLATE;ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE;BUTTPARK 20\09-21;AKOS BBS-00004493;5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;5-Amino-1-p-tolyl-1H-pyrazole-4-carboxylic acid ethyl ester
    3. CAS NO:15001-11-3
    4. Molecular Formula: C13H15N3O2
    5. Molecular Weight: 245.28
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 15001-11-3.mol
  • Chemical Properties

    1. Melting Point: 114-116°C
    2. Boiling Point: 394.8 °C at 760 mmHg
    3. Flash Point: 192.5 °C
    4. Appearance: /
    5. Density: 1.23 g/cm3
    6. Vapor Pressure: 1.93E-06mmHg at 25°C
    7. Refractive Index: 1.6
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    9. Solubility: N/A
    10. CAS DataBase Reference: ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE(15001-11-3)
    12. EPA Substance Registry System: ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE(15001-11-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 15001-11-3(Hazardous Substances Data)

15001-11-3 Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE is used as a building block for the synthesis of bioactive molecules, leveraging its unique chemical structure to create new pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE is utilized as a precursor in the development of new agrochemicals, potentially contributing to the creation of novel pesticides or other agricultural chemicals that can enhance crop protection and yield.

Check Digit Verification of cas no

The CAS Registry Mumber 15001-11-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,0,0 and 1 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 15001-11:
(7*1)+(6*5)+(5*0)+(4*0)+(3*1)+(2*1)+(1*1)=43
43 % 10 = 3
So 15001-11-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H15N3O2/c1-3-18-13(17)11-8-15-16(12(11)14)10-6-4-9(2)5-7-10/h4-8H,3,14H2,1-2H3

15001-11-3SDS

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 Ethyl 5-amino-1-(4-methylphenyl)-1H-pyrazole-4-carboxylate

1.2 Other means of identification

Product number -
Other names ETHYL 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE

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:15001-11-3 SDS

15001-11-3Relevant articles and documents

Novel Pyrazolo[3,4- d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Cheng, Xiang,Wang, Wei,Wang, Yunxiao,Xia, Dongguo,Yin, Fang,Liu, Qiaoyun,Luo, Huisheng,Li, Meng,Zhang, Chengqi,Cao, Haiqun,Lv, Xianhai

, p. 11395 - 11405 (2021/10/01)

Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition

Chen, Hui,Wang, Bin,Li, Peng,Yan, Hong,Li, Gang,Huang, Haihong,Lu, Yu

supporting information, (2021/03/26)

In this study, a series of sulfonamide compounds was designed and synthesized through the systematic optimization of the antibacterial agent sulfaphenazole for the treatment of Mycobacterium tuberculosis (M. tuberculosis). Preliminary results indicate that the 4-aminobenzenesulfonamide moiety plays a key role in maintaining antimycobacterial activity. Compounds 10c, 10d, 10f and 10i through the optimization on phenyl ring at the R2 site on the pyrazole displayed promising antimycobacterial activity paired with low cytotoxicity. In particular, compound 10d displayed good activity (MIC = 5.69 μg/mL) with low inhibition of CYP 2C9 (IC50 > 10 μM), consequently low potential risk of drug-drug interaction. These promising results provide new insight into the combination regimen using sulfonamide as one component for the treatment of M. tuberculosis.

Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

Liu, Hao,Ren, Zi-Li,Wang, Wei,Gong, Jie-Xiu,Chu, Ming-Jie,Ma, Quan-Wei,Wang, Jie-Chun,Lv, Xian-Hai

, p. 81 - 87 (2018/08/04)

The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.

A novel solid-phase synthetic method for production of N-alkyl-4-alkylamino-1-aryl-1H-pyrazolo[3,4-d]pyrimidine-6-carboxamide library

Heo, Yun-Jeong,Jeon, Moon-Kook

, p. 5959 - 5973 (2017/09/09)

This work describes a solid-phase synthetic method for building a compound library of N-alkyl-4-alkylamino-1-aryl-1H-pyrazolo[3,4-d]pyrimidine-6-carboxamide derivatives, that are based on the biologically active 1-aryl-1H-pyrazolo[3,4-d]pyrimidine scaffold. In the first step of this synthetic sequence, condensation reactions of ethyl 5-amino-1-aryl-1H-pyrazole-4-carboxylates with methyl cyanoformate resulted in the formation of esters that underwent hydrolysis to give 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one-6-carboxylic acids. The coupling reaction of these carboxylic acids with primary alkylamine-loaded acid-sensitive methoxybenzaldehyde (AMEBA) resins was followed by amination reactions mediated by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP). Subsequent cleavage from the solid support resulted in the formation of the target N-alkyl-4-alkylamino-1-aryl-1H-pyrazolo[3,4-d]pyrimidine-6-carboxamide derivatives. The reaction conditions for solid-phase transformations were optimized using a solution-phase model study with 2,4-dimethoxybenzyl-protected isobutylamine as a reactant in place of the AMEBA resin-loaded isobutylamine. The progress of the solid-phase reactions was monitored by on-bead ATR-FTIR spectroscopy. Diversification experiments were performed by using 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one-6-carboxylic acids and a variety of primary and secondary amine building blocks to build the target compound library.

A clean and rapid synthesis of 5-aminopyrazole-4-carboxylic acid esters and nitriles using montmorillonite K10

Jagath Reddy,Sailaja,Manjula,Srinivasa Rao,Khalilullah,Latha

, p. 385 - 388 (2007/10/03)

A series of 5-aminopyrazole-4-carboxylates (4a-f) and nitriles (5a-f) have been synthesized under heterogeneous catalytic conditions using montmorillonite.

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