3,5-Dimethylpyrazole

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3,5-Dimethylpyrazole
3,5-Dimethylpyrazole.jpg
3,5-Dimethylpyrazole.svg
Names
Preferred IUPAC name
3,5-Dimethyl-1H-pyrazole
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.597 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-657-5
PubChem CID
UNII
  • InChI=1S/C5H8N2/c1-4-3-5(2)7-6-4/h3H,1-2H3,(H,6,7)
    Key: SDXAWLJRERMRKF-UHFFFAOYSA-N
  • CC1=CC(=NN1)C
Properties
C5H8N2
Molar mass 96.133 g·mol−1
Appearancewhite solid
Density 1.027 g/cm3
Melting point 107.5 °C (225.5 °F; 380.6 K)
Boiling point 218 °C (424 °F; 491 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H302, H315, H319, H335, H361, H373
P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,5-Dimethylpyrazole is an organic compound with the formula (CH3C)2CHN2H. It is one of several isomeric derivatives of pyrazole that contain two methyl substituents. The compound is unsymmetrical but the corresponding conjugate acid (pyrazolium) and conjugate base (pyrazolide) have C2v symmetry. It is a white solid that dissolves well in polar organic solvents.

It is a precursor to a variety of ligands that are widely studied in coordination chemistry including trispyrazolylborate, a trispyrazolylmethane, and a pyrazolyldiphosphine. [1] [2]

Condensation of acetylacetone and hydrazine gives 3,5-dimethylpyrazole: [3]

CH3C(O)CH2C(O)CH3  +   N2H4   (CH3C)2CHN2H   +   2 H2O

It has found use as a blocking agent for isocyanates. [4]

Related Research Articles

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

<span class="mw-page-title-main">Acetylacetone</span> Chemical compound

Acetylacetone is an organic compound with the chemical formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion, a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.

<span class="mw-page-title-main">Scorpionate ligand</span> Tridentate ligand which "pinches" the central metal atom

The term scorpionate ligand refers to a tridentate (three-donor-site) ligand which would bind to a metal in a fac manner. The most popular class of scorpionates are the hydrotris(pyrazolyl)borates or Tp ligands. These were also the first to become popular. These ligands first appeared in journals in 1966 from the then little-known DuPont chemist of Ukrainian descent, Swiatoslaw Trofimenko. Trofimenko called this discovery "a new and fertile field of remarkable scope".

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, which are in ortho-substitution. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugate acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C3N2 with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol.

<span class="mw-page-title-main">Trispyrazolylborate</span>

The trispyrazolylborate ligand, abbreviated Tp, is an anionic tridentate and tripodal ligand. Trispyrazolylborate refers specifically to the anion [HB(C3N2H3)3], but the term trispyrazolylborate refers to derivatives substituted at on the pyrazolyl rings. This family of compounds are sometimes called scorpionate ligands.

<span class="mw-page-title-main">Methylidyne radical</span> Chemical compound

Methylidyne, or (unsubstituted) carbyne, is an organic compound whose molecule consists of a single hydrogen atom bonded to a carbon atom. It is the parent compound of the carbynes, which can be seen as obtained from it by substitution of other functional groups for the hydrogen.

<span class="mw-page-title-main">Lithium bis(trimethylsilyl)amide</span> Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si(CH3)3)2. It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.

<span class="mw-page-title-main">Bis(diphenylphosphino)methane</span> Chemical compound

1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2. Dppm, a white, crystalline powder, is used in inorganic and organometallic chemistry as a ligand. It is more specifically a chelating ligand because it is a ligand that can bond to metals with two phosphorus donor atoms. The natural bite angle is 73°.

Organoplatinum chemistry is the chemistry of organometallic compounds containing a carbon to platinum chemical bond, and the study of platinum as a catalyst in organic reactions. Organoplatinum compounds exist in oxidation state 0 to IV, with oxidation state II most abundant. The general order in bond strength is Pt-C (sp) > Pt-O > Pt-N > Pt-C (sp3). Organoplatinum and organopalladium chemistry are similar, but organoplatinum compounds are more stable and therefore less useful as catalysts.

<span class="mw-page-title-main">Potassium trispyrazolylborate</span> Chemical compound

Potassium trispyrazolylborate, commonly abbreviated KTp, is the potassium salt of the trispyrazolylborate ligand.

Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH
3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

<span class="mw-page-title-main">Potassium tris(3,5-dimethyl-1-pyrazolyl)borate</span> Chemical compound

Potassium tris(3,5-dimethyl-1-pyrazolyl)borate, abbreviated KTp*, is the potassium salt of the anion HB((CH3)2C3N2H)3. Tp* is a tripodal ligand that binds to a metal in a facial manner, more specifically a Scorpionate ligand. KTp* is a white crystalline solid that is soluble in polar solvents, including water and several alcohols.

<span class="mw-page-title-main">Hexahydro-1,3,5-triazine</span> Class of chemical compounds

In chemistry, hexahydro-1,3,5-triazine is a class of heterocyclic compounds with the formula (CH2NR)3. They are reduced derivatives of 1,3,5-triazine, which have the formula (CHN)3, a family of aromatic heterocycles. They are often called triazacyclohexanes or TACH's but this acronym is also applied to cis,cis-1,3,5-triaminocyclohexane.

<span class="mw-page-title-main">Transition-metal allyl complex</span>

Transition-metal allyl complexes are coordination complexes with allyl and its derivatives as ligands. Allyl is the radical with the connectivity CH2CHCH2, although as a ligand it is usually viewed as an allyl anion CH2=CH−CH2, which is usually described as two equivalent resonance structures.

<span class="mw-page-title-main">Tris(dimethylamino)methane</span> Chemical compound

Tris(dimethylamino)methane (TDAM) is the simplest representative of the tris(dialkylamino)methanes of the general formula (R2N)3CH in which three of the four of methane's hydrogen atoms are replaced by dimethylamino groups (−N(CH3)2). Tris(dimethylamino)methane can be regarded as both an amine and an orthoamide.

<span class="mw-page-title-main">Organotantalum chemistry</span> Chemistry of compounds containing a carbon-to-tantalum bond

Organotantalum chemistry is the chemistry of chemical compounds containing a carbon-to-tantalum chemical bond. A wide variety of compound have been reported, initially with cyclopentadienyl and CO ligands. Oxidation states vary from Ta(V) to Ta(-I).

<span class="mw-page-title-main">Transition metal nitrile complexes</span> Class of coordination compounds containing nitrile ligands (coordinating via N)

Transition metal nitrile complexes are coordination compounds containing nitrile ligands. Because nitriles are weakly basic, the nitrile ligands in these complexes are often labile.

Transition metal amino acid complexes are a large family of coordination complexes containing the conjugate bases of the amino acids, the 2-aminocarboxylates. Amino acids are prevalent in nature, and all of them function as ligands toward the transition metals. Not included in this article are complexes of the amides and ester derivatives of amino acids. Also excluded are the polyamino acids including the chelating agents EDTA and NTA.

Transition metal complexes of 2,2'-bipyridine are coordination complexes containing one or more 2,2'-bipyridine ligands. Complexes have been described for all of the transition metals. Although few have any practical value, these complexes have been influential. 2,2'-Bipyridine is classified as a diimine ligand. Unlike the structures of pyridine complexes, the two rings in bipy are coplanar, which facilitates electron delocalization. As a consequence of this delocalization, bipy complexes often exhibit distinctive optical and redox properties.

<span class="mw-page-title-main">Copper compounds</span> Chemical compounds containing copper

Copper forms a rich variety of compounds, usually with oxidation states +1 and +2, which are often called cuprous and cupric, respectively. Copper compounds, whether organic complexes or organometallics, promote or catalyse numerous chemical and biological processes.

References

  1. Reger, Daniel L.; Grattan, T.Christian; Brown, Kenneth J.; Little, Christine A.; Lamba, Jaydeep J.S.; Rheingold, Arnold L.; Sommer, Roger D. (2000). "Syntheses of tris(pyrazolyl)methane ligands and {[tris(pyrazolyl)methane]Mn(CO)3}SO3CF3 complexes: Comparison of ligand donor properties". Journal of Organometallic Chemistry. 607 (1–2): 120–128. doi:10.1016/S0022-328X(00)00290-4.
  2. Schenck, Terry G.; Downes, J. M.; Milne, C. R. C.; MacKenzie, Peter B.; Boucher, Terry G.; Whelan, John; Bosnich, B. (1985). "Bimetallic reactivity. Synthesis of bimetallic complexes containing a bis(phosphino)pyrazole ligand". Inorganic Chemistry. 24 (15): 2334–2337. doi:10.1021/ic00209a003.
  3. Johnson, William S.; Highet, Robert J. (1951). "3,5-Dimethylpyrazole". Organic Syntheses . 31: 43. doi:10.15227/orgsyn.031.0043.
  4. "Blocked Isocyanates" (PDF). Lanxess. June 2020. Archived (PDF) from the original on 2020-09-27.