263553-80-6

Basic information

• Product Name: ETHYL 2-(5-CHLORO-4-FORMYL-3-METHYL-1H-PYRAZOL-1-YL)ACETATE
• Synonyms: ETHYL 2-(5-CHLORO-4-FORMYL-3-METHYL-1H-PYRAZOL-1-YL)ACETATE;SPECS AN-742/37279044
• CAS NO: 263553-80-6
• Molecular Formula: C₉H₁₁ClN₂O₃
• Molecular Weight: 230.65
• Mol File: 263553-80-6.mol

Chemical Properties

• Melting Point: 66-68°C
• Boiling Point: 345.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• PKA: -1.20±0.10(Predicted)
• CAS DataBase Reference: ETHYL 2-(5-CHLORO-4-FORMYL-3-METHYL-1H-PYRAZOL-1-YL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(5-CHLORO-4-FORMYL-3-METHYL-1H-PYRAZOL-1-YL)ACETATE(263553-80-6)
• EPA Substance Registry System: ETHYL 2-(5-CHLORO-4-FORMYL-3-METHYL-1H-PYRAZOL-1-YL)ACETATE(263553-80-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 263553-80-6(Hazardous Substances Data)

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 30979-40-9 ethyl 2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)acetate 

Relevant articles and documents

Stereoselective synthesis of trans-3-functionalized-4-pyrazolo[5,1-b]thiazole-3-carboxylate substituted β-lactams: Potential synthons for diverse biologically active agents

An efficient protocol for the stereoselective synthesis of pyrazolo[5,1-b]thiazole-3-carboxylate tethered β-lactam conjugates 8a–j from novel pyrazolo [5,1-b]thiazole-3-carboxylate substituted Schiff’s bases 6a–f is reported here. The reaction between various ketene precursors and novel Schiff’s bases 6a–f afforded exclusive formation of trans-β-lactams 8a–j. The substrate scope of this approach was investigated extensively by varying different groups (R, Z). All the novel compounds were characterized using various spectroscopic techniques, such as FT-IR, 1H NMR, 13C NMR, elemental analysis, 13C NMR (DEPT-135), and mass spectrometry in representative cases. Single crystal X-ray crystallographic study of trans-ethyl 7-(1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl)-6-methyl-2-(methylthio)pyrazolo[5,1-b]thiazole-3-carboxylate 8a has confirmed the molecular structure and the stereochemical outcome. To the best of our knowledge, the synthesis of such types of Schiff’s bases and β-lactam conjugates has not been reported so far.

Facile synthesis of novel α-methylene-pyrazole-carboxylate substituted imines and trans-β-lactams: Versatile synthons for diverse heterocyclic molecules

A simple, facile, and high yielding stereoselective approach for the integration of α-methylene-pyrazole-carboxylates at the β-lactam nucleus is described. These monocyclic β-lactams have been synthesized by treatment of 2-phenoxy/benzylthio/phenylthio ethanoic acids or acetoxyacetyl chloride/phthalimidoacetyl chloride 5a–e with novel α-methylene-pyrazole-carboxylate imines 4a–c using Et3N and POCl3 in refluxing toluene. All of the newly synthesized α-methylene-pyrazole carboxylate imines 4a–c and their β-lactam derivatives 6a–h have been fully characterized by spectroscopic techniques such as FTIR, NMR (1H, 13C, and 13C DEPT-135), 2D-NMR (COSY and HSQC), and elemental analyses (CHN). The cycloaddition reaction was found to be highly stereoselective leading to the exclusive formation of trans-β-lactams 6a–h and trans configuration was assigned with respect to coupling constant values of C3-H and C4-H. The novel β-lactams 6a–h bearing α-methylene-pyrazole-carboxylate ring system will serve as useful synthons for highly functionalized acids, acetohydrazides/pyrazolones, alcohols, pyrazole carboxamides, peptides, and promising biologically active agents.

PYRAZOLOTHIAZOLE COMPOUND

A compound represented by the formula (I) or pharmacologically acceptable salt thereof exhibits an excellent CRF receptor antagonism wherein X is a nitrogen atom or CH; R1 is -A11-A12; A11 is a single bond or a C1-6 alkylene group; A12 is a hydrogen atom, a C1-6 alkyl group or a C3-6 cycloalkyl group, etc.; R2 is -A21-A22; A21 is a single bond or a C1-6 alkylene group; A22 is a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a non-aromatic heterocyclic group, or a heteroaryl group, etc.; R3 is a C 1-6 alkyl group, a C3-6 cycloalkyl group, a C1-6 alkoxy group, a C3-6 cycloalkoxy C1-6 alkyl group, di-C1-6 alkyl amino group, a halogen atom, a cyano group, a formyl group, or a carboxyl group, etc; R4 is a hydrogen atom or a C1-6 alkoxy group; R5 is a halogen atom, a C1-6 alkyl group, or a C1-6 alkoxy group; R6 is a hydrogen atom, a C1-6 alkyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, or a C1-6 alkyl sulfinyl group etc.; and R7 is a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 alkylthio group

A novel method for the synthesis of pyrazolo[5,1-b]thiazole

By a new tandem reaction, in which ethyl 1-pyrazolacetate reacted with carbon disulfide and iodomethane, pyrazolo[5,1-b]thiazole was synthesized. This was an easy method for the synthesis of this type of heterocyles.