433853
5-Chloro-3-methyl-1-phenyl-4-pyrazolecarboxaldehyde
99%
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About This Item
Formule empirique (notation de Hill) :
C11H9ClN2O
Numéro CAS:
Poids moléculaire :
220.65
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Essai
99%
Forme
solid
Pf
145-148 °C (lit.)
Groupe fonctionnel
aldehyde
chloro
Chaîne 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
Clé InChI
DKZPJLZXLKAMDO-UHFFFAOYSA-N
Description générale
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.[1] 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.[2] 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.[3]
Application
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[1]
- N1-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)thiosemicarbazone[1]
- pyrazole derivatives, which were pharmacologically evaluated for analgesic (tail flick) and anti-inflammatory (based on carrageenan-induced paw edema) activities[4]
- N′-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4- yl)methylene] 2/4-substituted hydrazides[5]
Mention d'avertissement
Warning
Mentions de danger
Conseils de prudence
Classification des risques
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Organes cibles
Respiratory system
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
dust mask type N95 (US), Eyeshields, Gloves
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Convenient Synthesis and Characterization of Pyrazolones and Schiff Bases.
Girisha KS and Kalluraya B.
Synthetic Communications, 42(20), 3097-3102 (2012)
New pyrazole derivatives of potential biological activity.
Farghaly A-R, et al.
ARKIVOC (Gainesville, FL, United States), 7, 228-241 (2012)
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)
Design and Synthesis of Pyrazolyl Thiosemicarbazones as New Anticonvulsants.
Deng XQ and Song MX.
Bull. Korean Chem. Soc., 35(9), 2733-2733 (2014)
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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