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5-Chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde

99%

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About This Item

Fórmula empírica (Notação de Hill):
C11H9ClN2O
Número CAS:
947-95-5
Peso molecular:
220.65
Número MDL:
MFCD00100755
Código UNSPSC:
12352100
ID de substância PubChem:
24867155
NACRES:
NA.22

Ensaio

99%

forma

solid

pf

145-148 °C (lit.)

cadeia de caracteres SMILES

Cc1nn(c(Cl)c1C=O)-c2ccccc2

InChI

1S/C11H9ClN2O/c1-8-10(7-15)11(12)14(13-8)9-5-3-2-4-6-9/h2-7H,1H3

chave InChI

DKZPJLZXLKAMDO-UHFFFAOYSA-N

Descrição geral

5-Chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde (5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde) can be synthesized from 3-methyl-1-phenyl-1Hpyrazol-5(4H)-one under Vilsmeier-Haack reaction conditions. Knoevenagel condensation of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde with ethylcyanoacetate at 0°C has been reported to afford ethyl-2-cyano-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-yl)propionate. It participates in the synthesis of 2-((5-phenoxy-3-methyl-1-phenyl-1H-pyrazol- 4-yl)methylene)hydrazinecarbothiomide derivatives with a potential anticonvulsant property.

Aplicação

5-Chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde (5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde) may be employed as starting material for the following syntheses:
  • 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde hydrazone
  • N1-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)thiosemicarbazone
  • pyrazole derivatives, which were pharmacologically evaluated for analgesic (tail flick) and anti-inflammatory (based on carrageenan-induced paw edema) activities
  • N′-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4- yl)methylene] 2/4-substituted hydrazides

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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New pyrazole derivatives of potential biological activity.
Farghaly A-R, et al.
ARKIVOC (Gainesville, FL, United States), 7, 228-241 (2012)
Convenient Synthesis and Characterization of Pyrazolones and Schiff Bases.
Girisha KS and Kalluraya B.
Synthetic Communications, 42(20), 3097-3102 (2012)
Design and Synthesis of Pyrazolyl Thiosemicarbazones as New Anticonvulsants.
Deng XQ and Song MX.
Bull. Korean Chem. Soc., 35(9), 2733-2733 (2014)
Pharmacological screening for anti-inflammatory, analgesic activity of pyrazolyl derivatives along with molecular docking studies.
Kaushik D, et al.
Medicinal Chemistry Research, 21(11), 3646-3655 (2012)
Darpan Kaushik et al.
European journal of medicinal chemistry, 45(9), 3943-3949 (2010-06-25)
A series of N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides were synthesized using appropriate synthetic route and characterized by elemental analysis and spectral data. The anticonvulsant activity of some of the synthesized compounds were evaluated against maximal electroshock induced seizure (MES) and subcutaneous pentylenetetrazol

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