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Sigma-Aldrich

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

99%

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About This Item

Empirical Formula (Hill Notation):
C11H9ClN2O
CAS Number:
947-95-5
Molecular Weight:
220.65
MDL number:
MFCD00100755
UNSPSC Code:
12352100
PubChem Substance ID:
24867155
NACRES:
NA.22

assay

99%

form

solid

mp

145-148 °C (lit.)

SMILES string

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

InChI key

DKZPJLZXLKAMDO-UHFFFAOYSA-N

General description

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.

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
  • 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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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)
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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