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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
288-13-1 YesY
ChEBI CHEBI:17241 YesY
ChEMBL ChEMBL15967 YesY
ChemSpider 1019 YesY
DrugBank DB02757 YesY
Jmol interactive 3D 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)
Basicity (pKb) 11.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Pyrazole is an 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. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).[1] Pyrazoles are also a class of compounds that have the ring C3N2 with adjacent nitrogen atoms.[2] 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:[3]

Pyrazoles synthesis.png

Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine. For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole:[4]

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.[5]

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, antifungal and antibacterial activities.

In 1959, the first natural pyrazole, 1-pyrazolyl-alanine, was isolated from seeds of watermelons[6][7]

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. ^ Dissociation constants of organic acids and bases
  2. ^ Eicher, T.; Hauptmann, S. (2003). The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications (2nd ed.). Wiley-VCH. ISBN 3-527-30720-6. 
  3. ^ 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. 
  4. ^ William S. Johnson and Robert J. Highet (1963). "3,5-Dimethylpyrazole". Org. Synth. ; Coll. Vol. 4, p. 351 
  5. ^ H. v. Pechmann (1898). "Pyrazol aus Acetylen und Diazomethan". Berichte der deutschen chemischen Gesellschaft 31 (3): 2950–51. doi:10.1002/cber.18980310363. 
  6. ^ Fowden; Noe, Ridd and White (1959). Proc. Chem. SOC.: 131.  Missing or empty |title= (help)
  7. ^ 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. 


Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Pyrazole — Please support Wikipedia.
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125 news items

 
WhaTech
Tue, 12 Jan 2016 05:48:33 -0800

The Global and Chinese Pyrazole Industry, 2010-2020 Market Research Report is a professional and in-depth study on the current state of the global Pyrazole industry with a focus on the Chinese market. The report provides key statistics on the market ...
 
Targeted News Service (subscription)
Mon, 01 Feb 2016 11:41:12 -0800

ALEXANDRIA, Va., Feb. 1 -- Merck Sharp & Dohme, Rahway, New Jersey, has been assigned a patent (9,242,981) developed by seven co-inventors for "fused pyrazole derivatives as novel ERK inhibitors." The co-inventors are Gerald W. Shipps Jr., ...

The Biological SCENE

The Biological SCENE
Fri, 18 Sep 2015 04:15:00 -0700

To run the reaction, chemists simply mix an arene with either an aromatic nitrogen heterocycle, such as imidazole or pyrazole, or an ammonia equivalent, such as ammonium carbamate, in the presence of an acridinium catalyst and the cocatalyst 2,2,6 ...

Toledo Blade

Toledo Blade
Sun, 06 Sep 2015 22:03:49 -0700

We have discovered that when the TRPC3 channel is closed by a drug called Pyrazole 10, fewer cells are dying. We then investigated how these cells were saved from dying. From our previous investigations and the work of others in this field, we were ...

CosmeticsDesign-Europe.com

CosmeticsDesign-Europe.com
Wed, 29 Jul 2015 02:51:12 -0700

The pyrazole salt has been found to combine good stability as a raw material and good shade intensity with a range of common couplers when formulated in hair dyeing composition. Submission I on the new hair dye was transmitted by Cosmetics Europe in ...
 
Beef Magazine
Sat, 24 Oct 2015 06:30:00 -0700

Tolfenpro utilizes a new active ingredient, Tolfenpyrad, in the pyrazole chemical class. It has a mode of action as a mitochondrial electron transport inhibitor, meaning that it prevents an insect's cells from producing the energy needed to function ...
 
CattleNetwork.com
Tue, 20 Oct 2015 20:33:45 -0700

Bayer HealthCare Animal Health announces Tolfenpro Insecticide Ear Tag, an ear tag option with a new active ingredient to help producers control horn flies and face flies in beef cattle, non-lactating dairy cattle and lactating dairy cattle. “Both horn ...
 
Chemical Watch (subscription)
Fri, 24 Jul 2015 03:22:38 -0700

The hair dye ingredient 1-hexyl 4,5-diamine pyrazole sulfate is safe for use at a maximum on-head concentration of 1.0%, the European Commission's Scientific Committee on Consumer Safety (SCCS) has concluded. The committee notes in its scientific ...
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