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Pyrazole
Full structural formula
Skeletal formula with numbers
Ball-and-stick model
Space-filling model
Names
IUPAC name
Pyrazole
Other names
1,2-Diazole
Identifiers
CAS number 288-13-1 YesY
ChEBI CHEBI:17241 YesY
ChEMBL ChEMBL15967 YesY
ChemSpider 1019 YesY
DrugBank DB02757 YesY
Jmol-3D images Image
KEGG C00481 YesY
PubChem 1048
Properties
C3H4N2
Molar mass 68.08 g·mol−1
Melting point 66 to 70 °C (151 to 158 °F; 339 to 343 K)
Boiling point 186 to 188 °C (367 to 370 °F; 459 to 461 K)
Acidity (pKa) 14.0
Basicity (pKb) 2.5
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Pyrazole is the organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms. Pyrazoles are also the class of compounds that have the ring C3N2 with adjacent nitrogen atoms.[1] A notable drug containing a pyrazole ring is celecoxib (Celebrex).

Preparation and reactions[edit]

Pyrazoles are synthesized by the reaction of α,β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation:[2]

Pyrazoles synthesis.png

Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine. For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole:[3]

CH3C(O)CH2C(O)CH3 + N2H4 → (CH3)2C3HN2H + 2 H2O

History[edit]

The term pyrazole was given to this class of compounds by German Chemist Ludwig Knorr in 1883.[citation needed] In a classical method developed by German chemist Hans von Pechmann in 1898, pyrazole was synthesized from acetylene and diazomethane.[4]

Conversion to scorpionates[edit]

Pyrazoles react with potassium borohydride to form a class of ligands known as scorpionate. Pyrazole itself reacts with potassium borohydride at high temperatures (~200 °C) to form a tridentate ligand known as Tp ligand:

KBH4 + 3 C3H3N2H → KBH(C3H3N2)3 + 3 H2

Occurrence and uses[edit]

Celecoxib, a pyrazole derivative used as an analgesic

In medicine, derivatives of pyrazoles are used for their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, tranquilizing, muscle relaxing, psychoanaleptic, anticonvulsant, monoamineoxidase inhibiting, antidiabetic and antibacterial activities.

In 1959, the first natural pyrazole, 1-pyrazolyl-alanine, was isolated from seeds of watermelons[5][6]

Related heterocycles[edit]

Imidazole is an analog of pyrazole with two non-adjacent nitrogen atoms. In isoxazole, another analog, the nitrogen atom in position 1 replaced by oxygen.

References[edit]

  1. ^ Eicher, T.; Hauptmann, S. (2003). The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications (2nd ed.). Wiley-VCH. ISBN 3-527-30720-6. 
  2. ^ A. Schmidt, A. Dreger (2011). "Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses". Curr. Org. Chem 15 (9): 1423–1463. doi:10.2174/138527211795378263. 
  3. ^ William S. Johnson and Robert J. Highet (1963). "3,5-Dimethylpyrazole". Org. Synth. ; Coll. Vol. 4, p. 351 
  4. ^ H. v. Pechmann (1898). "Pyrazol aus Acetylen und Diazomethan". Berichte der deutschen chemischen Gesellschaft 31 (3): 2950–51. doi:10.1002/cber.18980310363. 
  5. ^ Fowden; Noe, Ridd and White (1959). Proc. Chem. SOC.: 131.  Missing or empty |title= (help)
  6. ^ Noe, F F; L Fowden; Richmond, P. T. (1959). "alpha-Amino-beta-(pyrazolyl-N) propionic acid: a new amino-acid from Citrullus vulgaris (water melon)". Nature 184 (4688): 69–70. Bibcode:1959Natur.184...69B. doi:10.1038/184069a0. ISSN 0028-0836. 

Further reading[edit]

A. Schmidt, A. Dreger (2011). "Recent Advances in the Chemistry of Pyrazoles. Part 2. Reactions and N-Heterocyclic Carbenes of Pyrazole". Curr. Org. Chem. 15 (16): 2897 – 2970. doi:10.2174/138527211796378497. 


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Targeted News Service (subscription)
Tue, 10 Feb 2015 22:11:15 -0800

... for residues of the herbicide, halosulfuron-methyl, methyl 5-[(4,6-dimethoxy-2-pyrimidiny)amino] carbonylaminosulfonyl]-3-chloro-1-methyl-1 H-pyrazole-4-carboxylate, including its metabolites and degradates, in or on the raw agricultural ...
 
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Thu, 06 Nov 2014 09:15:00 -0800

The main structural feature of Taselisib is a seven-membered benzoxazepine core that is substituted with a functionalized pyrazole at one end and an N-isopropyl-3-methyl-1,2,4-triazole heterocycle at the other end. The discovery route to prepare the ...

reportingclimatescience.com

reportingclimatescience.com
Fri, 14 Nov 2014 02:53:09 -0800

This structure is held together by a combination of [N–H···N] hydrogen bonds between the terminal ​pyrazole rings and [π···π] stacking between the electron-rich pyrazoles and electron-poor ​tetrafluorobenzenes. Such a synergistic arrangement makes this ...
 
Phys.Org
Mon, 10 Nov 2014 08:00:25 -0800

The team demonstrated the effectiveness of the technique by using it to modify a wide variety of heterocyclic structures that are frequently present in drug molecules, including furans, benzofurans and benzothiophenes; indole, pyrrole, thiazole ...
 
Nashville Post (subscription)
Wed, 03 Dec 2014 10:19:05 -0800

US 8,901,125 entitled SUBSTITUTED BICYCLIC ALKOXY PYRAZOLE ANALOGS AS ALLOSTERIC MODULATORS OF MGLUR5 RECEPTORS invented by P. Jeffrey Conn, Brentwood, TN; Craig W. Lindsley, Brentwood, TN; Shaun R. Stauffer, Brentwood, TN ...

IPWatchdog.com

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Fri, 12 Sep 2014 05:00:00 -0700

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Thu, 18 Sep 2014 09:07:30 -0700

ipconazole (ISO), expected by 14 November. It will cover the endpoints of reproductive 2; STOT RE 2; acute toxicity 4; aquatic acute 1; and aquatic chronic 1;; 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]-1H-pyrazole-4-carboxamide. Expected ...

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